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Phenylephrine
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<h2 id="medical-uses">Medical uses</h2> <h3>Decongestant</h3> <p>Phenylephrine is used as an alternative to <a href="/facts/Pseudoephedrine/b2rMjnLv">pseudoephedrine</a> as a decongestant, whose availability has been restricted in some countries due to a potential for use in the illicit synthesis of <a href="/facts/Methamphetamine/vS1jloMe">methamphetamine</a>.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> Its efficacy as an oral decongestant has been questioned, with several independent studies finding that it provided no more relief to sinus congestion than a placebo.<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a><a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a><a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> </p><p>A 2007 meta-analysis concluded that the evidence for its effectiveness is insufficient,<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> though another meta-analysis published shortly thereafter by researchers from <a href="/facts/GlaxoSmithKline/NrnnxFNW">GlaxoSmithKline</a> found the standard 10-mg dose to be more effective than a placebo; however, the fact that GSK markets many products containing phenylephrine has raised some speculation regarding selective publishing and other controversial techniques.<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a> A 2007 study by <a href="/facts/Wyeth_Consumer_Healthcare/oaUm9fwY">Wyeth Consumer Healthcare</a> notes that 7 studies available in 1976 support the efficacy of phenylephrine at a 10 mg dosage.<a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> The <a href="/facts/Food_and_Drug_Administration/rCEnh9WB">Food and Drug Administration</a> withdrew the indication "for the temporary relief of nasal congestion associated with sinusitis" in 2007.<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> </p><p>Two studies published in 2009, examined the effects of phenylephrine on symptoms of <a href="/facts/Allergic_rhinitis/ukE6bkIs">allergic rhinitis</a> by exposing people to pollen in a controlled, indoor environment. Neither study was able to distinguish between the effects of phenylephrine or a placebo. Pseudoephedrine and <a href="/facts/Loratadine/u3kQ4AFM">loratadine</a>–<a href="/facts/Montelukast/x26tXFtK">montelukast</a> therapy were found to be significantly more effective than both phenylephrine and placebo.<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a><a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a> </p><p>Pseudoephedrine was previously much more commonly available in the United States. However, provisions of the <a href="/facts/Combat_Methamphetamine_Epidemic_Act_of_2005/b4C3X3Xw">Combat Methamphetamine Epidemic Act of 2005</a> placed restrictions on the sale in the United States of pseudoephedrine products to prevent the <a href="/facts/Clandestine_chemistry/7h0ljKSs">clandestine manufacture</a> of methamphetamine. Since 2004, phenylephrine has been increasingly marketed as a substitute for pseudoephedrine; some manufacturers have changed the active ingredients of products to avoid restrictions on sales.<a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> Phenylephrine has been off-patent for some time,[<i>when?</i>] and many generic brands are available. </p><p>In September 2023, an independent advisory committee to the U.S. <a href="/facts/Food_and_Drug_Administration/rCEnh9WB">Food and Drug Administration</a> (FDA) unanimously agreed that there is insufficient evidence showing that "orally administered phenylephrine is effective as a nasal decongestant".<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> The committee also unanimously believes that this does not need further study. The FDA responded to the committee, stating it would take its advice under advisement.<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a><a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a> In November 2024, the FDA proposed to remove oral phenylephrine as an active ingredient that can be used in over-the-counter (OTC) monograph drug products for the temporary relief of nasal congestion.<a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a> </p> <h3>Hemorrhoids</h3> <p><a href="/facts/Hemorrhoids/wlInkR8T">Hemorrhoids</a> are caused by swollen <a href="/facts/Veins/I6ycr6gF">veins</a> in the <a href="/facts/Rectal/caqqyk2e">rectal</a> area.<a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a> Phenylephrine can be used topically to prevent symptoms of hemorrhoids. Phenylephrine causes the constriction of vascular smooth muscle and is often used in the treatment of hemorrhoids to narrow the swollen veins and relieve the attendant pain. However, veins contain less vascular smooth muscle in their walls than arteries. Products for treatment may also include substances that will form a protective barrier over the inflamed area, resulting in less pain when <a href="/facts/Feces/r9HDKB8G">feces</a> are passed.<a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a> </p><p>Phenylephrine hydrochloride at 0.25% is used as a <a href="/facts/Vasoconstriction/9hdY0aR2">vasoconstrictor</a> in <a href="/facts/Suppository/26njDQ8o">suppository</a> formulations for hemorrhoid treatment.<a class="footnote-ref" id="fnref:43" href="#fn:43"><sup>43</sup></a> </p> <h3>Pupil dilation</h3> <p class="note">"Prefrin" redirects here. For the iron supplement, see <a href="/facts/Proferrin/okvPXPWP">Proferrin</a>.</p> <p>Phenylephrine is used as an eye drop to dilate the pupil to facilitate visualization of the retina. It is often used in combination with <a href="/facts/Tropicamide/r5ph8vFh">tropicamide</a> as a synergist when tropicamide alone is not sufficient. Narrow-angle <a href="/facts/Glaucoma/MWqWVNz3">glaucoma</a> is a <a href="/facts/Contraindication/HawhU8x9">contraindication</a> to phenylephrine use. As a <a href="/facts/Mydriasis/19r5uMvC">mydriatic</a>, it is available in 2.5% and 10% <a href="/facts/Eye_drop/TzKX8700">eye drops</a>. Phenylephrine eye drops are applied to the eye after a topical anesthetic is applied.<a class="footnote-ref" id="fnref:44" href="#fn:44"><sup>44</sup></a> </p> <h3>Intraocular bleeding</h3> <p>Phenylephrine has been used as an <a href="/facts/Intracameral_injection/dnHv2gWm">intracameral injection</a> into the anterior chamber of the eye to arrest <a href="/facts/Intraocular_hemorrhage/7mww2gUt">intraocular bleeding</a> occurring during <a href="/facts/Cataract/RzN7k7K2">cataract</a> and <a href="/facts/Glaucoma/MWqWVNz3">glaucoma</a> <a href="/facts/Eye_surgery/MIBdYG7w">surgery</a>.<a class="footnote-ref" id="fnref:45" href="#fn:45"><sup>45</sup></a> </p> <h3>Low blood pressure</h3> <p>Phenylephrine is commonly used as a <a href="/facts/Vasopressor/GPCuG4aT">vasopressor</a> to increase the blood pressure in unstable patients with <a href="/facts/Hypotension/BhrdVVRS">hypotension</a> (low blood pressure), especially resulting from <a href="/facts/Septic_shock/yc9mgmrz">septic shock</a>.<a class="footnote-ref" id="fnref:46" href="#fn:46"><sup>46</sup></a><a class="footnote-ref" id="fnref:47" href="#fn:47"><sup>47</sup></a> Such use is common in <a href="/facts/Surgery/fG8tWf5Y">surgery</a> and <a href="/facts/Anesthesia/b3MKVn8E">anesthesia</a> or critical-care practices;<a class="footnote-ref" id="fnref:48" href="#fn:48"><sup>48</sup></a><a class="footnote-ref" id="fnref:49" href="#fn:49"><sup>49</sup></a> it is especially useful in counteracting the hypotensive effect of <a href="/facts/Epidural/jlVdMFPe">epidural</a> and <a href="/facts/Spinal_anesthesia/lGtF5kRs">spinal anesthesia</a>, as well as the vasodilating effect of bacterial toxins and the inflammatory response in <a href="/facts/Sepsis/n52bkffJ">sepsis</a> and <a href="/facts/Systemic_inflammatory_response_syndrome/yBfYlqoA">systemic inflammatory response syndrome</a>. </p><p>Because of its <a href="/facts/Vasoconstriction/9hdY0aR2">vasoconstrictive</a> effect, phenylephrine can cause severe <a href="/facts/Necrosis/zCPsTeWx">necrosis</a> if it infiltrates the surrounding tissues. Because of this, it should be given through a central line if at all possible. Damage may be prevented or mitigated by infiltrating the tissue with the alpha-blocker <a href="/facts/Phentolamine/JgzR1e3k">phentolamine</a> by subcutaneous injection.<a class="footnote-ref" id="fnref:50" href="#fn:50"><sup>50</sup></a> </p><p>In clinical studies, phenylephrine, administered <a href="/facts/Intravenous_administration/AwwuD3Nu">intravenously</a>, increases blood pressure, decreases <a href="/facts/Cardiac_output/7JCDn6Ht">cardiac output</a>, increases cerebral blood flow, and decreases cerebral tissue oxygen saturation.<a class="footnote-ref" id="fnref:51" href="#fn:51"><sup>51</sup></a><a class="footnote-ref" id="fnref:52" href="#fn:52"><sup>52</sup></a> The decreases in cardiac output, increases in cerebral blood flow, and decreases in cerebral tissue oxygen saturation with phenylephrine are all related to the degree of blood pressure increase.<a class="footnote-ref" id="fnref:53" href="#fn:53"><sup>53</sup></a> The decrease in cardiac output is primarily due to a decrease in <a href="/facts/Heart_rate/YngB0bzg">heart rate</a> and a modest decrease in <a href="/facts/Stroke_volume/juA5JeW8">stroke volume</a>.<a class="footnote-ref" id="fnref:54" href="#fn:54"><sup>54</sup></a> The decrease in heart rate is due to activation of the <a href="/facts/Baroreflex/PuVw15ba">arterial baroreflex</a>, which regulates heart rate in response to changes in blood pressure.<a class="footnote-ref" id="fnref:55" href="#fn:55"><sup>55</sup></a><a class="footnote-ref" id="fnref:56" href="#fn:56"><sup>56</sup></a> Because of the decrease in cardiac output, phenylephrine is a <a href="/facts/Inotrope/A58XE1pa">negative inotropic agent</a>.<a class="footnote-ref" id="fnref:57" href="#fn:57"><sup>57</sup></a> Its effects on cardiac output and cerebral oxygenation are unfavorable, and on account of this, the use of phenylephrine in the treatment of intraoperative hypotension is now being recommended against and moved away from in favor of other agents without these adverse effects like <a href="/facts/Ephedrine/wxXefYXQ">ephedrine</a> and <a href="/facts/Dopamine/5gNy8Xkd">dopamine</a>.<a class="footnote-ref" id="fnref:58" href="#fn:58"><sup>58</sup></a><a class="footnote-ref" id="fnref:59" href="#fn:59"><sup>59</sup></a> </p><p>When taken orally, phenylephrine has a threshold dose of about 50 mg to affect the cardiovascular system, a dose at which the drug decreases heart rate and slightly increases arterial blood pressure.<a class="footnote-ref" id="fnref:60" href="#fn:60"><sup>60</sup></a> Additionally, an <a href="/facts/Over-the-counter_drug/QI3FcgRf">over-the-counter</a> dose of 60 mg produces a slight increase in heart rate with no detectable changes in blood pressure.<a class="footnote-ref" id="fnref:61" href="#fn:61"><sup>61</sup></a> However, other literature reports that doses over 15 mg affect the cardiovascular system, including increases in blood pressure and decreases in heart rate.<a class="footnote-ref" id="fnref:62" href="#fn:62"><sup>62</sup></a> Higher doses, like 150 mg, more robustly affect the cardiovascular system.<a class="footnote-ref" id="fnref:63" href="#fn:63"><sup>63</sup></a> </p> <h3>Other uses</h3> <p>Phenylephrine has been used in the treatment of <a href="/facts/Postural_orthostatic_tachycardia_syndrome/Xndeukmn">postural orthostatic tachycardia syndrome</a> (POTS).<a class="footnote-ref" id="fnref:64" href="#fn:64"><sup>64</sup></a> It has been found to improve <a href="/facts/Vascular_resistance/XPH12Hub">vascular resistance</a>, enhance circulatory support, and improve symptoms of <a href="/facts/Orthostatic_intolerance/zA0L1a6b">orthostatic intolerance</a> in people with the condition.<a class="footnote-ref" id="fnref:65" href="#fn:65"><sup>65</sup></a> It has been described as particularly effective in people with <a href="/facts/Neuropathy/2KjA7nyD">neuropathic</a> POTS.<a class="footnote-ref" id="fnref:66" href="#fn:66"><sup>66</sup></a> However, phenylephrine has not been specifically approved for the treatment of POTS and data on this use are limited.<a class="footnote-ref" id="fnref:67" href="#fn:67"><sup>67</sup></a> This is also the case with other medications used in the treatment of POTS.<a class="footnote-ref" id="fnref:68" href="#fn:68"><sup>68</sup></a> </p><p>Phenylephrine has been used in the treatment of <a href="/facts/Priapism/zUtLjmTe">priapism</a>.<a class="footnote-ref" id="fnref:69" href="#fn:69"><sup>69</sup></a><a class="footnote-ref" id="fnref:70" href="#fn:70"><sup>70</sup></a> </p> <h3>Available forms</h3> <p>Phenylephrine is available in the form of <a href="/facts/Oral_administration/vNQcvLVx">oral</a> <a href="/facts/Tablet_(pharmacy)/PcYmnjd0">tablets</a> and <a href="/facts/Syrup/sYS48lTx">syrups</a> for use as a <a href="/facts/Nasal_decongestant/Vthbc5a0">nasal decongestant</a>, as an <a href="/facts/Intravenous/AwwuD3Nu">intravenous</a> <a href="/facts/Solution_(chemistry)/MGchhMQV">solution</a> to treat <a href="/facts/Hypotension/BhrdVVRS">hypotension</a>, as an <a href="/facts/Ophthalmology/024hdTWF">ophthalmic</a> solution, spray, or <a href="/facts/Eye_drop/TzKX8700">eye drop</a> to cause <a href="/facts/Pupil_dilation/0wP5p5KL">pupil dilation</a>, and as a <a href="/facts/Cocoa_butter/QYplogvG">cocoa butter</a> <a href="/facts/Suppository/26njDQ8o">suppository</a>, among other forms.<a class="footnote-ref" id="fnref:71" href="#fn:71"><sup>71</sup></a><a class="footnote-ref" id="fnref:72" href="#fn:72"><sup>72</sup></a> It was also previously available as a metered <a href="/facts/Aerosol/X1jXFLp2">aerosol</a> for <a href="/facts/Inhalational_administration/eB5VlguF">inhalation</a>, but this formulation was discontinued.<a class="footnote-ref" id="fnref:73" href="#fn:73"><sup>73</sup></a> </p><p>Phenylephrine is available both alone and in <a href="/facts/Combination_drug/pVS5UD72">combination</a> with other drugs.<a class="footnote-ref" id="fnref:74" href="#fn:74"><sup>74</sup></a><a class="footnote-ref" id="fnref:75" href="#fn:75"><sup>75</sup></a> These other drugs include <a href="/facts/Antihistamine/HuMC25lt">antihistamines</a> like <a href="/facts/Chlorpheniramine/fuBFmrko">chlorpheniramine</a>, <a href="/facts/Doxylamine/sCBJP1sc">doxylamine</a>, <a href="/facts/Promethazine/aN03q5Fv">promethazine</a>, and <a href="/facts/Mepyramine/XXqnuPQa">mepyramine</a> (pyrilamine); <a href="/facts/Analgesic/xLj4XBcq">analgesics</a> like <a href="/facts/Paracetamol/SNDfQWcf">paracetamol</a> (acetaminophen), <a href="/facts/Ibuprofen/vsKBTfVl">ibuprofen</a>, <a href="/facts/Ketorolac/rakTnlbx">ketorolac</a>, and <a href="/facts/Codeine/lr7WHXmX">codeine</a>; <a href="/facts/Cough_suppressant/2Qe0AjMx">cough suppressants</a> like <a href="/facts/Dextromethorphan/Jq9UgD4M">dextromethorphan</a>; <a href="/facts/Expectorant/rw9veqmh">expectorants</a> like <a href="/facts/Guiafenesin/6M5ShWzC">guiafenesin</a>; <a href="/facts/Anticholinergic/9mDjo23r">anticholinergics</a> like <a href="/facts/Cyclopentolate/oAPkYWXz">cyclopentolate</a> and <a href="/facts/Tropicamide/r5ph8vFh">tropicamide</a>; and <a href="/facts/Beta_agonist/YaDyG1pI">β-adrenergic receptor agonists</a> like <a href="/facts/Isoprenaline/5mE9d4Fx">isoprenaline</a> (isoproterenol).<a class="footnote-ref" id="fnref:76" href="#fn:76"><sup>76</sup></a><a class="footnote-ref" id="fnref:77" href="#fn:77"><sup>77</sup></a> It is used in combination with antihistamines and analgesics in cough and cold preparations, with anticholinergics in ophthalmic formulations, and with β-adrenergic receptor agonists in inhalational forms.<a class="footnote-ref" id="fnref:78" href="#fn:78"><sup>78</sup></a><a class="footnote-ref" id="fnref:79" href="#fn:79"><sup>79</sup></a> Intravenous phenylephrine is always formulated by itself.<a class="footnote-ref" id="fnref:80" href="#fn:80"><sup>80</sup></a> </p> <h2 id="contraindications">Contraindications</h2> <p>Phenylephrine is <a href="/facts/Contraindication/HawhU8x9">contraindicated</a> in people with <a href="/facts/Hypertension/wlAvBfcf">hypertension</a>, <a href="/facts/Hyperthyroidism/H9Eqmbgk">hyperthyroidism</a>, and <a href="/facts/Heart_disease/HD420nMv">heart disease</a> due to its <a href="/facts/Vasoconstriction/9hdY0aR2">vasoconstrictor</a> effects.<a class="footnote-ref" id="fnref:81" href="#fn:81"><sup>81</sup></a> Relative contraindications include people with <a href="/facts/Raynaud%27s_syndrome/VorWr74H">Raynaud's syndrome</a> due to vasoconstriction, those taking <a href="/facts/Monoamine_oxidase_inhibitor/obewT56a">monoamine oxidase inhibitors</a> (MAOIs) due to inhibition of the metabolism of phenylephrine, and people with <a href="/facts/Prostate/mrBdSsf7">prostate</a> problems due to potential exacerbation of <a href="/facts/Urinary_retention/YvTCprKk">urinary retention</a>.<a class="footnote-ref" id="fnref:82" href="#fn:82"><sup>82</sup></a><a class="footnote-ref" id="fnref:83" href="#fn:83"><sup>83</sup></a> </p> <h2 id="side-effects">Side effects</h2> <p>Phenylephrine taken orally at indicated doses is usually <a href="/facts/Tolerability/bIv7laJh">well-tolerated</a>.<a class="footnote-ref" id="fnref:84" href="#fn:84"><sup>84</sup></a> It may cause <a href="/facts/Side_effect/PhuX2haY">side effects</a> such as <a href="/facts/Headache/mdmmC9DP">headache</a>, <a href="/facts/Reflex_bradycardia/5IQbplys">reflex bradycardia</a>, <a href="/facts/Stimulation/qTbolu55">excitability</a>, <a href="/facts/Psychomotor_agitation/n1vWk6RD">restlessness</a>, and <a href="/facts/Cardiac_arrhythmia/ooEpr46Q">cardiac arrhythmias</a>.<a class="footnote-ref" id="fnref:85" href="#fn:85"><sup>85</sup></a> At higher than indicated doses, phenylephrine can increase <a href="/facts/Blood_pressure/VtqqSM2J">blood pressure</a> and decrease <a href="/facts/Heart_rate/YngB0bzg">heart rate</a>.<a class="footnote-ref" id="fnref:86" href="#fn:86"><sup>86</sup></a> A 45 mg dose of phenylephrine can increase systolic blood pressure by 20 mmHg.<a class="footnote-ref" id="fnref:87" href="#fn:87"><sup>87</sup></a> Possible <a href="/facts/Side_effect/PhuX2haY">side effects</a> of <a href="/facts/Intravenous_administration/AwwuD3Nu">intravenous</a> phenylephrine are <a href="/facts/Dose_dependency/DLcuLdHc">dose-dependent</a> and may include <a href="/facts/Bradycardia/70msP5HD">bradycardia</a> and <a href="/facts/Hypertension/wlAvBfcf">reactive hypertension</a>.<a class="footnote-ref" id="fnref:88" href="#fn:88"><sup>88</sup></a> </p> <h3>Heart</h3> <p>The primary side effect of phenylephrine is <a href="/facts/Hypertension/wlAvBfcf">high blood pressure</a>. People with high blood pressure are typically advised to avoid products containing it. Because this medication is a <a href="/facts/Sympathomimetic/IEYU5ERW">sympathomimetic</a> amine without <a href="/facts/%CE%92-adrenergic_receptor/uoAeJbcN">β-adrenergic receptor</a> <a href="/facts/Agonist/nz8U5NNp">agonist</a> activity, it does not increase contractility force and output of the cardiac muscle. It may increase blood pressure resulting in a <a href="/facts/Reflex_bradycardia/5IQbplys">slow heart rate</a> through stimulation of vascular (likely carotid) baroreceptors. A common side effect during IV administration is reflex bradycardia.<a class="footnote-ref" id="fnref:89" href="#fn:89"><sup>89</sup></a> The low concentration eye drops do not cause blood pressure changes and the changes with the higher dose drops do not last long.<a class="footnote-ref" id="fnref:90" href="#fn:90"><sup>90</sup></a> </p><p>The cardiovascular effects of phenylephrine may be potentiated in people with <a href="/facts/Hypertension/wlAvBfcf">hypertension</a>.<a class="footnote-ref" id="fnref:91" href="#fn:91"><sup>91</sup></a> <a href="/facts/Hypertensive_crisis/dDPo1RB3">Hypertensive crisis</a> with phenylephrine <a href="/facts/Eye_drop/TzKX8700">eye drops</a> has been reported in people with hypertension.<a class="footnote-ref" id="fnref:92" href="#fn:92"><sup>92</sup></a> In people with underlying <a href="/facts/Cardiovascular_disease/HD420nMv">cardiovascular disease</a>, phenylephrine has been found to increase blood pressure and cause associated impairment in myocardial perfusion.<a class="footnote-ref" id="fnref:93" href="#fn:93"><sup>93</sup></a> Other reported side effects of phenylephrine have included increased blood pressure, <a href="/facts/Vasoconstriction/9hdY0aR2">vasoconstriction</a> resulting in <a href="/facts/Orthostatic_hypotension/pkeTyF8w">worsened orthostatic tolerance</a>, <a href="/facts/Atrial_fibrillation/Rzkq1tmN">atrial fibrillation</a> following <a href="/facts/Coronary_artery_bypass_surgery/DDTF1jaB">coronary artery bypass surgery</a>, <a href="/facts/Cerebral_hypoxia/rKLaKRC3">decreased cerebral oxygenation</a>, bradycardia in people with <a href="/facts/Spinal_cord_injury/D0vo3ArR">spinal cord injury</a>, <a href="/facts/Cardiac_arrhythmia/ooEpr46Q">cardiac arrhythmias</a>, <a href="/facts/Pulmonary_edema/sVS5UDxl">pulmonary edema</a>, <a href="/facts/Myocardial_infarction/xoGw0qcG">myocardial infarction</a>, and <a href="/facts/Microvascular_occlusion/gAErCF9G">microvascular occlusion syndrome</a>.<a class="footnote-ref" id="fnref:94" href="#fn:94"><sup>94</sup></a> Rarely, <a href="/facts/Stroke/DwpjdzY0">stroke</a> has been reported with phenylephrine, including in the oral, topical, and intravenous forms.<a class="footnote-ref" id="fnref:95" href="#fn:95"><sup>95</sup></a> </p><p>Due to the increased risk of side effects in people with hypertension, phenylephrine is not suggested for use in this population.<a class="footnote-ref" id="fnref:96" href="#fn:96"><sup>96</sup></a><a class="footnote-ref" id="fnref:97" href="#fn:97"><sup>97</sup></a> </p> <h3>Others</h3> <p><a href="/facts/Prostatic_hyperplasia/ocGSCVK9">Prostatic hyperplasia</a> can also be worsened by use, and chronic use can lead to rebound <a href="/facts/Hyperemia/Snf41s0k">hyperemia</a>.<a class="footnote-ref" id="fnref:98" href="#fn:98"><sup>98</sup></a> People with a history of anxiety or panic disorders, or on anticonvulsant medication for epilepsy should not take this substance. The drug interaction might produce seizures. Some patients have been shown to have an upset stomach, severe abdominal cramping, and vomiting issues connected to taking this drug.<a class="footnote-ref" id="fnref:99" href="#fn:99"><sup>99</sup></a> </p><p>Phenylephrine is pregnancy category C. Due to the lack of studies done in animals and in humans, it is not known whether there is harm to the fetus. Phenylephrine should only be given to pregnant women who have a clear need.<a class="footnote-ref" id="fnref:100" href="#fn:100"><sup>100</sup></a> </p><p>Extended use may cause <a href="/facts/Rhinitis_medicamentosa/EedknaIe">rhinitis medicamentosa</a>, a condition of <a href="/facts/Rebound_effect/ngI6B2gB">rebound</a> <a href="/facts/Nasal_congestion/xClWzxrg">nasal congestion</a>.<a class="footnote-ref" id="fnref:101" href="#fn:101"><sup>101</sup></a> </p> <h2 id="interactions">Interactions</h2> <p>Phenylephrine is susceptible to <a href="/facts/Drug_metabolism/I5nQ28Ma">metabolism</a> by <a href="/facts/Monoamine_oxidase/4bJuxUFy">monoamine oxidase</a>.<a class="footnote-ref" id="fnref:102" href="#fn:102"><sup>102</sup></a><a class="footnote-ref" id="fnref:103" href="#fn:103"><sup>103</sup></a> Because of this, <a href="/facts/Monoamine_oxidase_inhibitor/obewT56a">monoamine oxidase inhibitors</a> (MAOIs) can inhibit the metabolism of phenylephrine and increase exposure to the medication.<a class="footnote-ref" id="fnref:104" href="#fn:104"><sup>104</sup></a><a class="footnote-ref" id="fnref:105" href="#fn:105"><sup>105</sup></a> Whereas a 45 mg oral dose of phenylephrine alone increases <a href="/facts/Systolic_blood_pressure/VtqqSM2J">systolic blood pressure</a> by 20 mmHg, use of this dose in people on MAOIs increases systolic blood pressure by more than 60 mmHg.<a class="footnote-ref" id="fnref:106" href="#fn:106"><sup>106</sup></a> </p><p>Phenylephrine can interact with other <a href="/facts/Adrenergic/7rl3jv45">adrenergic</a> drugs, such as <a href="/facts/Beta_blocker/PRsWgpLV">beta blockers</a> like <a href="/facts/Propranolol/QvH2XYt1">propranolol</a>, <a href="/facts/Alpha-1_blocker/IFz841Cn">α1-adrenergic receptor antagonists</a> like <a href="/facts/Chlorpromazine/oFja1FYA">chlorpromazine</a>, <a href="/facts/Alpha-2_agonist/dWAlxo8z">α2-adrenergic receptor agonists</a> like <a href="/facts/Clonidine/xPebaeST">clonidine</a>, <a href="/facts/Norepinephrine_reuptake_inhibitor/UW3udbj0">norepinephrine reuptake inhibitors</a> like <a href="/facts/Atomoxetine/Pg9hgoYx">atomoxetine</a> and <a href="/facts/Amitriptyline/7YGkJGfr">amitriptyline</a>, and MAOIs (which increase norepinephrine levels).<a class="footnote-ref" id="fnref:107" href="#fn:107"><sup>107</sup></a> It can also interact with <a href="/facts/Corticosteroid/jeL2QeIL">corticosteroids</a> like <a href="/facts/Prednisone/eGgPIauI">prednisone</a>, which sensitize the vasculature to sympathomimetics and augment their vasoconstrictive effects, and with <a href="/facts/Ergot_alkaloid/7Uw5WeoP">ergot alkaloids</a>, which also have <a href="/facts/Vasoconstriction/9hdY0aR2">vasoconstrictor</a> effects and can have additive or synergistic effects with phenylephrine.<a class="footnote-ref" id="fnref:108" href="#fn:108"><sup>108</sup></a> In addition, combination of phenylephrine with other <a href="/facts/Sympathomimetic/IEYU5ERW">sympathomimetic</a> drugs can increase <a href="/facts/Pressor/GPCuG4aT">pressor</a> effects and the risk of hemorrhagic stroke.<a class="footnote-ref" id="fnref:109" href="#fn:109"><sup>109</sup></a> Other drugs that may decrease the effects of phenylephrine may include <a href="/facts/Calcium_channel_blockers/st91pD2K">calcium channel blockers</a>, <a href="/facts/ACE_inhibitors/cHT1Yxub">ACE inhibitors</a> and <a href="/facts/Benzodiazepine/IgbJr4jy">benzodiazepines</a>.<a class="footnote-ref" id="fnref:110" href="#fn:110"><sup>110</sup></a> Patients taking these medications may need a higher dose of phenylephrine to achieve a comparable increase in blood pressure.<a class="footnote-ref" id="fnref:111" href="#fn:111"><sup>111</sup></a> Concomitant use of phenylephrine with the preceding agents may necessitate dose adjustments. </p><p><a href="/facts/Acetaminophen/SNDfQWcf">Acetaminophen</a> (paracetamol) has been found to increase exposure to oral phenylephrine.<a class="footnote-ref" id="fnref:112" href="#fn:112"><sup>112</sup></a> It more than doubles phenylephrine's <a href="/facts/Bioavailability/9l6na9MV">bioavailability</a>, reduces its <a href="/facts/Absorption_(pharmacokinetics)/LCezQPJK">absorption</a> half-time by 50%, increases phenylephrine levels by approximately 2-fold, and increases peak phenylephrine levels by 4-fold, with substantial <a href="/facts/Interindividual_variability/f2wzYLbI">interindividual variability</a>.<a class="footnote-ref" id="fnref:113" href="#fn:113"><sup>113</sup></a> Phenylephrine is widely formulated with acetaminophen in combination products.<a class="footnote-ref" id="fnref:114" href="#fn:114"><sup>114</sup></a> The combination may increase the cardiovascular effects of phenylephrine.<a class="footnote-ref" id="fnref:115" href="#fn:115"><sup>115</sup></a> The mechanism of the interaction between phenylephrine and acetaminophen is unknown, but it has been suggested that it may be due to saturation of <a href="/facts/Sulfation/lI6B3Y1M">sulfation</a> <a href="/facts/Metabolic_pathway/8Py8HKJd">pathways</a> by acetaminophen that also participate in phenylephrine metabolism.<a class="footnote-ref" id="fnref:116" href="#fn:116"><sup>116</sup></a> </p> <h2 id="pharmacology">Pharmacology</h2> <h3>Pharmacodynamics</h3> <p>Phenylephrine is a <a href="/facts/Binding_selectivity/RryTsdGv">selective</a> <a href="/facts/Agonist/nz8U5NNp">agonist</a> of the <a href="/facts/%CE%911-adrenergic_receptor/JbPCT974">α1-adrenergic receptor</a>, one of the <a href="/facts/Biological_target/7bakbMFR">biological targets</a> of the <a href="/facts/Catecholamine/hHFrCMgM">catecholamine</a> <a href="/facts/Hormone/WFnBnINJ">hormones</a> and <a href="/facts/Neurotransmitter/LlpYFSU3">neurotransmitters</a> <a href="/facts/Epinephrine/k7vvMI7E">epinephrine</a> (adrenaline) and <a href="/facts/Norepinephrine/AjTIC9ox">norepinephrine</a> (noradrenaline).<a class="footnote-ref" id="fnref:117" href="#fn:117"><sup>117</sup></a><a class="footnote-ref" id="fnref:118" href="#fn:118"><sup>118</sup></a><a class="footnote-ref" id="fnref:119" href="#fn:119"><sup>119</sup></a> It is a <a href="/facts/Full_agonist/nz8U5NNp">full agonist</a> of the α1-adrenergic receptor in most assessed <a href="/facts/Tissue_(biology)/H7CpML7A">tissues</a>.<a class="footnote-ref" id="fnref:120" href="#fn:120"><sup>120</sup></a> The drug has weak, minimal, or no agonist activity at the <a href="/facts/%CE%912-adrenergic_receptor/QmUrvvYn">α2-adrenergic receptor</a> or the <a href="/facts/%CE%92-adrenergic_receptor/uoAeJbcN">β-adrenergic receptors</a>.<a class="footnote-ref" id="fnref:121" href="#fn:121"><sup>121</sup></a><a class="footnote-ref" id="fnref:122" href="#fn:122"><sup>122</sup></a><a class="footnote-ref" id="fnref:123" href="#fn:123"><sup>123</sup></a> At the β-adrenergic receptors, it is a <a href="/facts/Partial_agonist/VLm2vmgU">partial agonist</a>.<a class="footnote-ref" id="fnref:124" href="#fn:124"><sup>124</sup></a> </p><p>Phenylephrine also has relatively little or no activity as a <a href="/facts/Norepinephrine_releasing_agent/Ua8s5KKG">norepinephrine releasing agent</a>.<a class="footnote-ref" id="fnref:125" href="#fn:125"><sup>125</sup></a><a class="footnote-ref" id="fnref:126" href="#fn:126"><sup>126</sup></a> As such, it has little activity as an indirectly acting <a href="/facts/Sympathomimetic/IEYU5ERW">sympathomimetic</a> and non-selective activator of <a href="/facts/Adrenergic_receptor/uoAeJbcN">adrenergic receptors</a>.<a class="footnote-ref" id="fnref:127" href="#fn:127"><sup>127</sup></a><a class="footnote-ref" id="fnref:128" href="#fn:128"><sup>128</sup></a> This is in contrast to related sympathomimetics like <a href="/facts/Pseudoephedrine/b2rMjnLv">pseudoephedrine</a>.<a class="footnote-ref" id="fnref:129" href="#fn:129"><sup>129</sup></a> However, more recent research suggests that phenylephrine may actually be more <a href="/facts/Potency_(pharmacology)/D38FDyPh">potent</a> as a norepinephrine releasing agent than has previously been thought.<a class="footnote-ref" id="fnref:130" href="#fn:130"><sup>130</sup></a> This might help to explain certain unexpected <a href="/facts/Pharmacodynamics/zdvfFshl">pharmacodynamic</a> effects of the drug.<a class="footnote-ref" id="fnref:131" href="#fn:131"><sup>131</sup></a> </p><p>Because of its α1-adrenergic receptor agonism, phenylephrine is a directly acting sympathomimetic <a href="/facts/Vasoconstrictor/9hdY0aR2">vasoconstrictor</a><a class="footnote-ref" id="fnref:132" href="#fn:132"><sup>132</sup></a><a class="footnote-ref" id="fnref:133" href="#fn:133"><sup>133</sup></a> and produces both <a href="/facts/Vein/I6ycr6gF">venous</a> and <a href="/facts/Artery/Y1Yj0jat">arterial</a> <a href="/facts/Vasoconstriction/9hdY0aR2">vasoconstriction</a>.<a class="footnote-ref" id="fnref:134" href="#fn:134"><sup>134</sup></a><a class="footnote-ref" id="fnref:135" href="#fn:135"><sup>135</sup></a> The term <i>sympathomimetic</i> means that it mimics the actions of epinephrine or norepinephrine.<a class="footnote-ref" id="fnref:136" href="#fn:136"><sup>136</sup></a> </p><p>Phenylephrine works as a <a href="/facts/Nasal_decongestant/Vthbc5a0">nasal decongestant</a> by causing local vasoconstriction in the nose.<a class="footnote-ref" id="fnref:137" href="#fn:137"><sup>137</sup></a> Whereas the related sympathomimetic decongestant <a href="/facts/Pseudoephedrine/b2rMjnLv">pseudoephedrine</a> causes both vasoconstriction and increase of <a href="/facts/Mucociliary_clearance/1RKhjzVd">mucociliary clearance</a> through its non-specific adrenergic activity, phenylephrine's selective α1-adrenergic receptor agonism causes vasoconstriction alone, resulting in a difference in their methods of action. </p> <h3>Pharmacokinetics</h3> <h4>Absorption</h4> <p>Phenylephrine is rapidly <a href="/facts/Absorption_(pharmacokinetics)/LCezQPJK">absorbed</a> from the <a href="/facts/Gastrointestinal_tract/nK2zwqBS">gastrointestinal tract</a> when taken <a href="/facts/Oral_administration/vNQcvLVx">orally</a>.<a class="footnote-ref" id="fnref:138" href="#fn:138"><sup>138</sup></a> However, its absorption is incomplete and erratic.<a class="footnote-ref" id="fnref:139" href="#fn:139"><sup>139</sup></a> Because of extensive <a href="/facts/First-pass_metabolism/jfDsbq7S">first-pass metabolism</a>, phenylephrine has an oral <a href="/facts/Bioavailability/9l6na9MV">bioavailability</a> of only about 38% relative to <a href="/facts/Intravenous_administration/AwwuD3Nu">intravenous administration</a>.<a class="footnote-ref" id="fnref:140" href="#fn:140"><sup>140</sup></a><a class="footnote-ref" id="fnref:141" href="#fn:141"><sup>141</sup></a><a class="footnote-ref" id="fnref:142" href="#fn:142"><sup>142</sup></a><a class="footnote-ref" id="fnref:143" href="#fn:143"><sup>143</sup></a> However, another source has stated that the bioavailability of phenylephrine is poorly documented and may actually be as low as 0.003%.<a class="footnote-ref" id="fnref:144" href="#fn:144"><sup>144</sup></a> The <a href="/facts/Tmax_(pharmacology)/IceQcRQB">time to peak</a> concentrations is 1.0 to 1.3 hours.<a class="footnote-ref" id="fnref:145" href="#fn:145"><sup>145</sup></a> </p> <h4>Distribution</h4> <p>The <a href="/facts/Steady-state_(pharmacokinetics)/x4CUUnle">steady-state</a> <a href="/facts/Volume_of_distribution/64B8XegG">volume of distribution</a> of phenylephrine is 340 L.<a class="footnote-ref" id="fnref:146" href="#fn:146"><sup>146</sup></a> </p><p>Phenylephrine does not cross the <a href="/facts/Blood%E2%80%93brain_barrier/xYzvVwdu">blood–brain barrier</a> and hence is a <a href="/facts/Peripherally_selective_drug/Jzzu4aSg">peripherally selective drug</a> with no <a href="/facts/Central_nervous_system/k8I6To97">central nervous system</a> activity.<a class="footnote-ref" id="fnref:147" href="#fn:147"><sup>147</sup></a><a class="footnote-ref" id="fnref:148" href="#fn:148"><sup>148</sup></a><a class="footnote-ref" id="fnref:149" href="#fn:149"><sup>149</sup></a><a class="footnote-ref" id="fnref:150" href="#fn:150"><sup>150</sup></a> Its lack of blood-brain barrier permeability is related to its <a href="/facts/Hydroxyl_group/1Hs2QAEv">hydroxyl groups</a> and high <a href="/facts/Hydrophilicity/k8p95WYu">hydrophilicity</a>.<a class="footnote-ref" id="fnref:151" href="#fn:151"><sup>151</sup></a><a class="footnote-ref" id="fnref:152" href="#fn:152"><sup>152</sup></a> The lack of central permeation with phenylephrine is in contrast to certain other related decongestant and sympathomimetic agents like <a href="/facts/Pseudoephedrine/b2rMjnLv">pseudoephedrine</a>, <a href="/facts/Ephedrine/wxXefYXQ">ephedrine</a>, and <a href="/facts/Phenylpropanolamine/Bp2fDnBs">phenylpropanolamine</a>.<a class="footnote-ref" id="fnref:153" href="#fn:153"><sup>153</sup></a><a class="footnote-ref" id="fnref:154" href="#fn:154"><sup>154</sup></a><a class="footnote-ref" id="fnref:155" href="#fn:155"><sup>155</sup></a> </p> <h4>Metabolism</h4> <p>Phenylephrine is <a href="/facts/Metabolism/WxDrm8k5">metabolized</a> in the <a href="/facts/Intestine/nK2zwqBS">intestines</a> and <a href="/facts/Liver/Rtp4Fk2b">liver</a> prior to reaching the systemic circulation when taken orally.<a class="footnote-ref" id="fnref:156" href="#fn:156"><sup>156</sup></a> It is extensively metabolized during first-pass metabolism due to susceptibility to <a href="/facts/Monoamine_oxidase/4bJuxUFy">monoamine oxidases</a>, similarly to <a href="/facts/Epinephrine/k7vvMI7E">epinephrine</a>.<a class="footnote-ref" id="fnref:157" href="#fn:157"><sup>157</sup></a><a class="footnote-ref" id="fnref:158" href="#fn:158"><sup>158</sup></a><a class="footnote-ref" id="fnref:159" href="#fn:159"><sup>159</sup></a><a class="footnote-ref" id="fnref:160" href="#fn:160"><sup>160</sup></a> Phenylephrine is metabolized via <a href="/facts/Oxidation/Pyd5RVcj">oxidative</a> <a href="/facts/Deamination/aBIhMC23">deamination</a> by both <a href="/facts/MAO-A/VXqw1LUU">MAO-A</a> and <a href="/facts/MAO-B/wa0xq7KL">MAO-B</a>.<a class="footnote-ref" id="fnref:161" href="#fn:161"><sup>161</sup></a><a class="footnote-ref" id="fnref:162" href="#fn:162"><sup>162</sup></a><a class="footnote-ref" id="fnref:163" href="#fn:163"><sup>163</sup></a> In contrast to epinephrine and <a href="/facts/Norepinephrine/AjTIC9ox">norepinephrine</a>, phenylephrine is not a <a href="/facts/Catecholamine/hHFrCMgM">catecholamine</a>, and is not metabolized by <a href="/facts/Catechol_O-methyltransferase/GlKMEABG">catechol O-methyltransferase</a> (COMT).<a class="footnote-ref" id="fnref:164" href="#fn:164"><sup>164</sup></a> Besides monoamine oxidase, phenylephrine is also metabolized by <a href="/facts/Sulfation/lI6B3Y1M">sulfation</a> and <a href="/facts/Glucuronidation/G5qfwsFb">glucuronidation</a> <a href="/facts/Conjugation_(biochemistry)/WYyXtFIU">conjugation</a>.<a class="footnote-ref" id="fnref:165" href="#fn:165"><sup>165</sup></a><a class="footnote-ref" id="fnref:166" href="#fn:166"><sup>166</sup></a> Non-oral routes of phenylephrine, like <a href="/facts/Intranasal_administration/W0hvb0gd">intranasal</a>, <a href="/facts/Ophthalmic_drug_administration/VlyFY5Nl">ophthalmic</a>, and <a href="/facts/Parenteral_administration/LsyoHTzH">parenteral</a>, do not undergo first-pass metabolism in the gastrointestinal tract.<a class="footnote-ref" id="fnref:167" href="#fn:167"><sup>167</sup></a> </p><p>The major <a href="/facts/Metabolite/nAyywVtA">metabolite</a> of phenylephrine is <a href="https://pubchem.ncbi.nlm.nih.gov/compound/3-Hydroxymandelic-acid"><i>meta</i>-hydroxymandelic acid</a>, which is inactive.<a class="footnote-ref" id="fnref:168" href="#fn:168"><sup>168</sup></a><a class="footnote-ref" id="fnref:169" href="#fn:169"><sup>169</sup></a> Lesser metabolites of phenylephrine include <a href="/facts/Sulfate/yuWVxsUf">sulfate</a> and <a href="/facts/Glucuronide/I1EMKqWM">glucuronide</a> conjugates, which are also inactive.<a class="footnote-ref" id="fnref:170" href="#fn:170"><sup>170</sup></a><a class="footnote-ref" id="fnref:171" href="#fn:171"><sup>171</sup></a> </p><p>Unlike phenylephrine, related sympathomimetics with a <a href="/facts/Methyl_group/fkM97EMD">methyl group</a> at the α carbon (i.e., <a href="/facts/Substituted_amphetamine/KlmrodPb">amphetamines</a>), like <a href="/facts/Ephedrine/wxXefYXQ">ephedrine</a>, <a href="/facts/Pseudoephedrine/b2rMjnLv">pseudoephedrine</a>, <a href="/facts/Phenylpropanolamine/Bp2fDnBs">phenylpropanolamine</a>, <a href="/facts/Methoxamine/jsIMY4Ky">methoxamine</a>, and <a href="/facts/Methoxyphenamine/z6tbKjzs">methoxyphenamine</a>, are resistant to degradation by monoamine oxidase.<a class="footnote-ref" id="fnref:172" href="#fn:172"><sup>172</sup></a> </p> <h4>Elimination</h4> <p>Phenylephrine is primarily <a href="/facts/Excretion/mspsTfnv">excreted</a> in <a href="/facts/Urine/oNUYVtvX">urine</a>.<a class="footnote-ref" id="fnref:173" href="#fn:173"><sup>173</sup></a><a class="footnote-ref" id="fnref:174" href="#fn:174"><sup>174</sup></a> It is recovered 86% in urine.<a class="footnote-ref" id="fnref:175" href="#fn:175"><sup>175</sup></a> The drug is excreted in urine 3 to 16% unchanged, 57% as <a href="https://pubchem.ncbi.nlm.nih.gov/compound/3-Hydroxymandelic-acid"><i>meta</i>-hydroxymandelic acid</a>, and 8% as <a href="/facts/Sulfate/yuWVxsUf">sulfate</a> <a href="/facts/Conjugation_(biochemistry)/WYyXtFIU">conjugates</a>.<a class="footnote-ref" id="fnref:176" href="#fn:176"><sup>176</sup></a><a class="footnote-ref" id="fnref:177" href="#fn:177"><sup>177</sup></a> <a href="/facts/Glucuronide/I1EMKqWM">Glucuronide</a> conjugates constitute a smaller portion of phenylephrine.<a class="footnote-ref" id="fnref:178" href="#fn:178"><sup>178</sup></a> </p><p>Phenylephrine has a relatively short <a href="/facts/Elimination_half-life/7nB2JtMr">elimination half-life</a> of 2.0 to 3.0 hours regardless of <a href="/facts/Route_of_administration/LsyoHTzH">route of administration</a>.<a class="footnote-ref" id="fnref:179" href="#fn:179"><sup>179</sup></a><a class="footnote-ref" id="fnref:180" href="#fn:180"><sup>180</sup></a><a class="footnote-ref" id="fnref:181" href="#fn:181"><sup>181</sup></a><a class="footnote-ref" id="fnref:182" href="#fn:182"><sup>182</sup></a><a class="footnote-ref" id="fnref:183" href="#fn:183"><sup>183</sup></a> Its lack of metabolism by COMT is said to be responsible for its much longer <a href="/facts/Duration_of_action/zdvfFshl">duration of action</a> than related agents like <a href="/facts/Norepinephrine/AjTIC9ox">norepinephrine</a>.<a class="footnote-ref" id="fnref:184" href="#fn:184"><sup>184</sup></a> </p> <h2 id="chemistry">Chemistry</h2> <p>Phenylephrine is a <a href="/facts/Substituted_phenethylamine/dte6TQxS">substituted phenethylamine</a> and can also be referred to <a href="/facts/Chemical_structure/r5rT1Lj4">structurally</a> as (<i>R</i>)-β,3-dihydroxy-<i>N</i>-methylphenethylamine.<a class="footnote-ref" id="fnref:185" href="#fn:185"><sup>185</sup></a><a class="footnote-ref" id="fnref:186" href="#fn:186"><sup>186</sup></a><a class="footnote-ref" id="fnref:187" href="#fn:187"><sup>187</sup></a> It is closely <a href="/facts/Structural_analog/3aysWSVG">structurally related</a> to <a href="/facts/Epinephrine/k7vvMI7E">epinephrine</a> (adrenaline; 3,4,β-trihydroxy-<i>N</i>-methylphenethylamine), differing from it only in the absence of one <a href="/facts/Hydroxyl_group/1Hs2QAEv">hydroxyl group</a> on the <a href="/facts/Phenyl_ring/Ql9Yx5uu">phenyl ring</a>.<a class="footnote-ref" id="fnref:188" href="#fn:188"><sup>188</sup></a> It is a <a href="/facts/Chirality/hjx0eGrB">chiral</a> compound and is used as the <a href="/facts/Enantiopure_drug/D2UlXdtH">enantiopure</a> (<i>R</i>)-<a href="/facts/Stereoisomer/I3kzlDE8">stereoisomer</a>.<a class="footnote-ref" id="fnref:189" href="#fn:189"><sup>189</sup></a><a class="footnote-ref" id="fnref:190" href="#fn:190"><sup>190</sup></a> The <a href="/facts/Racemic_mixture/STEagtrD">racemic</a> form has not been formally named or used.<a class="footnote-ref" id="fnref:191" href="#fn:191"><sup>191</sup></a> </p><p>Phenylephrine is the <i>N</i>-<a href="/facts/Methyl_group/fkM97EMD">methylated</a> <a href="/facts/Chemical_derivative/JYcbLkbm">derivative</a> of <a href="/facts/Norfenefrine/hzfQkGEz">norfenefrine</a> (3,β-dihydroxyphenethylamine).<a class="footnote-ref" id="fnref:192" href="#fn:192"><sup>192</sup></a> The <a href="/facts/Racemic_mixture/STEagtrD">racemic</a> <i>N</i>-<a href="/facts/Ethyl_group/ydVhnBwD">ethyl</a> <a href="/facts/Structural_analog/3aysWSVG">analogue</a> is <a href="/facts/Etilefrine/4flQgCcH">etilefrine</a> (ethylphenephrine).<a class="footnote-ref" id="fnref:193" href="#fn:193"><sup>193</sup></a> <a href="/facts/Synephrine/c4SecSgp">Synephrine</a> (<i>p</i>-synephrine, oxedrine; 4,β-dihydroxyphenethylamine) is a <a href="/facts/Positional_isomer/vEQEBbWQ">positional isomer</a> of phenylephrine.<a class="footnote-ref" id="fnref:194" href="#fn:194"><sup>194</sup></a> In contrast to epinephrine and <a href="/facts/Norepinephrine/AjTIC9ox">norepinephrine</a> (noradrenaline; 3,4,β-trihydroxyphenethylamine), phenylephrine is not a <a href="/facts/Catecholamine/hHFrCMgM">catecholamine</a> since it does not have two hydroxyl groups on its phenyl ring.<a class="footnote-ref" id="fnref:195" href="#fn:195"><sup>195</sup></a> Besides the catecholamines, the chemical structure of phenylephrine somewhat resembles that of <a href="/facts/Amphetamine/yKIpLJ9E">amphetamine</a> (α-methylphenethylamine).<a class="footnote-ref" id="fnref:196" href="#fn:196"><sup>196</sup></a> However, phenylephrine does not have a <a href="/facts/Methyl_group/fkM97EMD">methyl group</a> at the α <a href="/facts/Carbon/ukrgQexo">carbon</a> and hence is not an amphetamine itself.<a class="footnote-ref" id="fnref:197" href="#fn:197"><sup>197</sup></a> </p><p>Phenylephrine is a <a href="/facts/Small_molecule/kbwq3VBn">small-molecule</a> compound with the <a href="/facts/Molecular_formula/hghUtthl">molecular formula</a> C9H13NO2 and a <a href="/facts/Molecular_weight/FWueGMed">molecular weight</a> of 167.205 g/mol.<a class="footnote-ref" id="fnref:198" href="#fn:198"><sup>198</sup></a><a class="footnote-ref" id="fnref:199" href="#fn:199"><sup>199</sup></a> It is a highly <a href="/facts/Hydrophilic/k8p95WYu">hydrophilic</a> compound, with an experimental <a href="/facts/Partition_coefficient/D4aTlBal">log P</a> of -0.3.<a class="footnote-ref" id="fnref:200" href="#fn:200"><sup>200</sup></a><a class="footnote-ref" id="fnref:201" href="#fn:201"><sup>201</sup></a><a class="footnote-ref" id="fnref:202" href="#fn:202"><sup>202</sup></a> Phenylephrine is used medically almost always as the <a href="/facts/Hydrochloride/7Sdqua4a">hydrochloride</a> <a href="/facts/Salt_(chemistry)/lsSKwGpn">salt</a>.<a class="footnote-ref" id="fnref:203" href="#fn:203"><sup>203</sup></a><a class="footnote-ref" id="fnref:204" href="#fn:204"><sup>204</sup></a> However, the <a href="/facts/Free_base/bLMkVbTk">free base</a> form and the <a href="/facts/Tannate/sop1UP0T">tannate</a> salt have also been used pharmaceutically to a much lesser extent.<a class="footnote-ref" id="fnref:205" href="#fn:205"><sup>205</sup></a> </p><p><a href="/facts/Pivenfrine/c0rb7PVt">Pivenfrine</a> is the 3-<a href="/facts/Pivalate/dDnDBbo0">pivalate</a> <a href="/facts/Ester/FoUAIIw4">ester</a> of phenylephrine and has much greater <a href="/facts/Lipophilicity/AWpsR8Xe">lipophilicity</a> in comparison.<a class="footnote-ref" id="fnref:206" href="#fn:206"><sup>206</sup></a><a class="footnote-ref" id="fnref:207" href="#fn:207"><sup>207</sup></a> </p> <h2 id="history">History</h2> <p>Phenylephrine was first patented in 1927 and was first introduced for medical use in 1938.<a class="footnote-ref" id="fnref:208" href="#fn:208"><sup>208</sup></a> </p> <h2 id="society-and-culture">Society and culture</h2> <h3>Names</h3> <p>Phenylephrine is the <a href="/facts/Generic_term/nENLNhIF">generic name</a> of the drug and its <a href="/facts/International_Nonproprietary_Name/wYL655x6">INN</a>Tooltip International Nonproprietary Name, <a href="/facts/British_Approved_Name/pm1t52SQ">BAN</a>Tooltip British Approved Name, and <a href="/facts/D%C3%A9nomination_Commune_Fran%C3%A7aise/Kvfl1AVE">DCF</a>Tooltip Dénomination Commune Française, while its <a href="/facts/United_States_Adopted_Name/5AFEKGfQ">USAN</a>Tooltip United States Adopted Name and <a href="/facts/British_Approved_Name/pm1t52SQ">BANM</a>Tooltip British Approved Name in the case of the <a href="/facts/Hydrochloride/7Sdqua4a">hydrochloride</a> <a href="/facts/Salt_(chemistry)/lsSKwGpn">salt</a> are phenylephrine hydrochloride.<a class="footnote-ref" id="fnref:209" href="#fn:209"><sup>209</sup></a><a class="footnote-ref" id="fnref:210" href="#fn:210"><sup>210</sup></a><a class="footnote-ref" id="fnref:211" href="#fn:211"><sup>211</sup></a><a class="footnote-ref" id="fnref:212" href="#fn:212"><sup>212</sup></a> Synonyms of phenylephrine include phenephrine, fenefrine, L-m-synephrine, metaoxedrine, neo-oxedrine, mesatonum, neosynephrine, and m-sympatol.<a class="footnote-ref" id="fnref:213" href="#fn:213"><sup>213</sup></a><a class="footnote-ref" id="fnref:214" href="#fn:214"><sup>214</sup></a><a class="footnote-ref" id="fnref:215" href="#fn:215"><sup>215</sup></a> Brand names of phenylephrine include Neosynephrine or Neo-Synephrine and Sudafed PE, among numerous others.<a class="footnote-ref" id="fnref:216" href="#fn:216"><sup>216</sup></a><a class="footnote-ref" id="fnref:217" href="#fn:217"><sup>217</sup></a><a class="footnote-ref" id="fnref:218" href="#fn:218"><sup>218</sup></a><a class="footnote-ref" id="fnref:219" href="#fn:219"><sup>219</sup></a> </p> <h3>Availability</h3> <p>Phenylephrine is available worldwide as a <a href="/facts/Prescription_drug/a2zNYPMq">prescription drug</a> in many different <a href="/facts/Pharmaceutical_form/ahtNIMrF">formulations</a>.<a class="footnote-ref" id="fnref:220" href="#fn:220"><sup>220</sup></a> </p> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Richards E, Lopez MJ, Maani CV (2023). "Phenylephrine". StatPearls. Treasure Island, Florida: StatPearls Publishing. PMID 30521222. Retrieved 27 April 2023. <a href="http://www.ncbi.nlm.nih.gov/books/NBK534801/" target="_blank">http://www.ncbi.nlm.nih.gov/books/NBK534801/</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Joint Formulary Committee (2018). BNF 76 : September 2018 - March 2019. London: British Medical Association, Royal Pharmaceutical Society of Great Britain. pp. 188–189. ISBN 9780857113382. OCLC 1021215075. <a href="9780857113382" target="_blank">9780857113382</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Richards E, Lopez MJ, Maani CV (2023). "Phenylephrine". StatPearls. Treasure Island, Florida: StatPearls Publishing. PMID 30521222. Retrieved 27 April 2023. <a href="http://www.ncbi.nlm.nih.gov/books/NBK534801/" target="_blank">http://www.ncbi.nlm.nih.gov/books/NBK534801/</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Joint Formulary Committee (2018). BNF 76 : September 2018 - March 2019. London: British Medical Association, Royal Pharmaceutical Society of Great Britain. pp. 188–189. ISBN 9780857113382. OCLC 1021215075. <a href="9780857113382" target="_blank">9780857113382</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Richards E, Lopez MJ, Maani CV (2023). "Phenylephrine". StatPearls. Treasure Island, Florida: StatPearls Publishing. PMID 30521222. Retrieved 27 April 2023. <a href="http://www.ncbi.nlm.nih.gov/books/NBK534801/" target="_blank">http://www.ncbi.nlm.nih.gov/books/NBK534801/</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Eccles R (January 2007). "Substitution of phenylephrine for pseudoephedrine as a nasal decongeststant. An illogical way to control methamphetamine abuse". Br J Clin Pharmacol. 63 (1): 10–14. doi:10.1111/j.1365-2125.2006.02833.x. PMC 2000711. PMID 17116124. PE and PDE are sympathomimetic vasoconstrictors that are closely related to adrenaline in structure, as illustrated in Figure 1. PE differs chemically from adrenaline only in the absence of one hydroxyl group from the benzene ring. [...] PE is a relatively selective α1 agonist. It has weak α2 adrenoceptor agonist activity and low β agonist activity. Most of the α1 agonist activity is due to a direct action on α receptors with relatively little indirect effect via noradrenaline release [11]. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2000711" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2000711</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>O'Donnell SR (March 1995). "Sympathomimetic vasoconstrictors as nasal decongestants". Med J Aust. 162 (5): 264–267. doi:10.5694/j.1326-5377.1995.tb139882.x. PMID 7534374. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>U.S. patent 1,932,347, application 1928, expired 1950 <a href="https://patents.google.com/patent/US1932347" target="_blank">https://patents.google.com/patent/US1932347</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 541. ISBN 9783527607495. <a href="9783527607495" target="_blank">9783527607495</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> <li id="fn:17"><p>Joint Formulary Committee (2018). BNF 76 : September 2018 - March 2019. London: British Medical Association, Royal Pharmaceutical Society of Great Britain. pp. 188–189. ISBN 9780857113382. OCLC 1021215075. <a href="9780857113382" target="_blank">9780857113382</a> <a href="#fnref:17" class="footnote-back-ref">↩</a></p></li> <li id="fn:18"><p>"Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023. <a href="https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals" target="_blank">https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals</a> <a href="#fnref:18" class="footnote-back-ref">↩</a></p></li> <li id="fn:19"><p>"First Generic Drug Approvals 2023". U.S. Food and Drug Administration (FDA). 30 May 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023. <a href="https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals" target="_blank">https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals</a> <a href="#fnref:19" class="footnote-back-ref">↩</a></p></li> <li id="fn:20"><p>"Max Strength Decongestant Tablets" (PDF). www.mhra.gov.uk. p. 10. Archived from the original (PDF) on 19 August 2019. Retrieved 10 January 2019. <a href="https://web.archive.org/web/20190819052429/http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con014437.pdf" target="_blank">https://web.archive.org/web/20190819052429/http://www.mhra.gov.uk/home/groups/par/documents/websiteresources/con014437.pdf</a> <a href="#fnref:20" class="footnote-back-ref">↩</a></p></li> <li id="fn:21"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:21" class="footnote-back-ref">↩</a></p></li> <li id="fn:22"><p>Hatton RC, Hendeles L (March 2022). "Why Is Oral Phenylephrine on the Market After Compelling Evidence of Its Ineffectiveness as a Decongestant?". Ann Pharmacother. 56 (11): 1275–1278. doi:10.1177/10600280221081526. PMID 35337187. S2CID 247712448. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:22" class="footnote-back-ref">↩</a></p></li> <li id="fn:23"><p>Lowe D (March 2022). "The Uselessness of Phenylephrine". Science (blog). <a href="https://www.science.org/content/blog-post/uselessness-phenylephrine" target="_blank">https://www.science.org/content/blog-post/uselessness-phenylephrine</a> <a href="#fnref:23" class="footnote-back-ref">↩</a></p></li> <li id="fn:24"><p>Christensen J (12 September 2023). "Popular OTC medicines for colds and allergies don't work, FDA panel says". CNN. Retrieved 12 September 2023. <a href="https://www.cnn.com/2023/09/12/health/phenylephrine-tablets-ineffective-fda-panel-says/index.html" target="_blank">https://www.cnn.com/2023/09/12/health/phenylephrine-tablets-ineffective-fda-panel-says/index.html</a> <a href="#fnref:24" class="footnote-back-ref">↩</a></p></li> <li id="fn:25"><p>"FDA Proposes Ending Use of Oral Phenylephrine as OTC Monograph Nasal Decongestant Active Ingredient After Extensive Review". U.S. Food and Drug Administration (FDA) (Press release). 7 November 2024. Retrieved 10 November 2024. <a href="https://www.fda.gov/news-events/press-announcements/fda-proposes-ending-use-oral-phenylephrine-otc-monograph-nasal-decongestant-active-ingredient-after" target="_blank">https://www.fda.gov/news-events/press-announcements/fda-proposes-ending-use-oral-phenylephrine-otc-monograph-nasal-decongestant-active-ingredient-after</a> <a href="#fnref:25" class="footnote-back-ref">↩</a></p></li> <li id="fn:26"><p>Presley B, Bianchi B, Coleman J, Diamond F, McNally G (July 2018). "Efficiency of extraction and conversion of pseudoephedrine to methamphetamine from tamper-resistant and non-tamper-resistant formulations". Journal of Pharmaceutical and Biomedical Analysis. 156: 16–22. doi:10.1016/j.jpba.2018.04.016. PMID 29684907. S2CID 13660478. <a href="https://doi.org/10.1016%2Fj.jpba.2018.04.016" target="_blank">https://doi.org/10.1016%2Fj.jpba.2018.04.016</a> <a href="#fnref:26" class="footnote-back-ref">↩</a></p></li> <li id="fn:27"><p>Horak F, Zieglmayer P, Zieglmayer R, Lemell P, Yao R, Staudinger H, et al. (February 2009). "A placebo-controlled study of the nasal decongestant effect of phenylephrine and pseudoephedrine in the Vienna Challenge Chamber". Annals of Allergy, Asthma & Immunology. 102 (2): 116–20. doi:10.1016/S1081-1206(10)60240-2. PMID 19230461. Phenylephrine was not significantly different from placebo in the primary end point. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:27" class="footnote-back-ref">↩</a></p></li> <li id="fn:28"><p>Day JH, Briscoe MP, Ratz JD, Danzig M, Yao R (April 2009). "Efficacy of loratadine-montelukast on nasal congestion in patients with seasonal allergic rhinitis in an environmental exposure unit". Annals of Allergy, Asthma & Immunology. 102 (4): 328–38. doi:10.1016/S1081-1206(10)60339-0. PMID 19441605. There were no statistically significant differences between phenylephrine and placebo for any measures. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:28" class="footnote-back-ref">↩</a></p></li> <li id="fn:29"><p>Hendeles L, Hatton RC (July 2006). "Oral phenylephrine: an ineffective replacement for pseudoephedrine?". The Journal of Allergy and Clinical Immunology. 118 (1): 279–80. doi:10.1016/j.jaci.2006.03.002. PMID 16815167. <a href="https://doi.org/10.1016%2Fj.jaci.2006.03.002" target="_blank">https://doi.org/10.1016%2Fj.jaci.2006.03.002</a> <a href="#fnref:29" class="footnote-back-ref">↩</a></p></li> <li id="fn:30"><p>Hatton RC, Winterstein AG, McKelvey RP, Shuster J, Hendeles L (March 2007). "Efficacy and safety of oral phenylephrine: systematic review and meta-analysis". The Annals of Pharmacotherapy. 41 (3): 381–90. doi:10.1345/aph.1H679. PMID 17264159. S2CID 25627664. Archived from the original (abstract) on 27 February 2007.(published online Jan 2007) <a href="https://web.archive.org/web/20070227143703/http://www.theannals.com/cgi/content/abstract/aph.1H679v1" target="_blank">https://web.archive.org/web/20070227143703/http://www.theannals.com/cgi/content/abstract/aph.1H679v1</a> <a href="#fnref:30" class="footnote-back-ref">↩</a></p></li> <li id="fn:31"><p>Kollar C, Schneider H, Waksman J, Krusinska E (June 2007). "Meta-analysis of the efficacy of a single dose of phenylephrine 10 mg compared with placebo in adults with acute nasal congestion due to the common cold". Clinical Therapeutics. 29 (6): 1057–70. doi:10.1016/j.clinthera.2007.05.021. PMID 17692721. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:31" class="footnote-back-ref">↩</a></p></li> <li id="fn:32"><p>Desjardins PJ, Berlin RG (October 2007). "Efficacy of phenylephrine". British Journal of Clinical Pharmacology. 64 (4): 555–6, author reply 557. doi:10.1111/j.1365-2125.2007.02935.x. PMC 2048561. PMID 17610531. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2048561" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2048561</a> <a href="#fnref:32" class="footnote-back-ref">↩</a></p></li> <li id="fn:33"><p>"Phenylephrine Monograph for Professionals". Drugs.com. AHFS. 2 March 2022. Retrieved 9 May 2022. However, efficacy of oral phenylephrine for this use [as a decongestant] has been questioned. <a href="https://www.drugs.com/monograph/phenylephrine.html" target="_blank">https://www.drugs.com/monograph/phenylephrine.html</a> <a href="#fnref:33" class="footnote-back-ref">↩</a></p></li> <li id="fn:34"><p>Horak F, Zieglmayer P, Zieglmayer R, Lemell P, Yao R, Staudinger H, et al. (February 2009). "A placebo-controlled study of the nasal decongestant effect of phenylephrine and pseudoephedrine in the Vienna Challenge Chamber". Annals of Allergy, Asthma & Immunology. 102 (2): 116–20. doi:10.1016/S1081-1206(10)60240-2. PMID 19230461. Phenylephrine was not significantly different from placebo in the primary end point. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:34" class="footnote-back-ref">↩</a></p></li> <li id="fn:35"><p>Day JH, Briscoe MP, Ratz JD, Danzig M, Yao R (April 2009). 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