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Amoxicillin
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<h2 id="medical-uses">Medical uses</h2> <p>Amoxicillin is used in the treatment of a number of infections, including <a href="/facts/Acute_otitis_media/m9g53GBM">acute otitis media</a>, <a href="/facts/Streptococcal_pharyngitis/bp4ATM2j">streptococcal pharyngitis</a>, <a href="/facts/Pneumonia/Jw0KquTA">pneumonia</a>, <a href="/facts/Cellulitis/hCIm7nzQ">skin infections</a>, <a href="/facts/Urinary_tract_infection/4NwY9tL0">urinary tract infections</a>, <i><a href="/facts/Salmonella/2SkCRybG">Salmonella</a></i> infections, <a href="/facts/Lyme_disease/820IycaC">Lyme disease</a>, and <a href="/facts/Chlamydia_infection/bcKTIM1L">chlamydia</a> infections.<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a><a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a> </p> <h3>Acute otitis media</h3> <p>Children with acute otitis media who are younger than six months of age are generally treated with amoxicillin or other antibiotics. Although most children with acute otitis media who are older than two years old do not benefit from treatment with amoxicillin or other antibiotics, such treatment may be helpful in children younger than two years old with acute otitis media that is bilateral or accompanied by ear drainage.<a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a> In the past, amoxicillin was dosed three times daily when used to treat acute otitis media, which resulted in missed doses in routine <a href="/facts/Ambulatory_care/AXaQLHqJ">ambulatory practice</a>. There is now evidence that two-times daily dosing or once-daily dosing has similar effectiveness.<a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a> </p> <h3>Respiratory infections</h3> <p>Most sinusitis infections are caused by <a href="/facts/Virus/mf88Bcbl">viruses</a>, for which amoxicillin and amoxicillin-clavulanate are ineffective,<a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a> and the small benefit gained by amoxicillin may be overridden by the adverse effects.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> Amoxicillin is considered the first-line <a href="/facts/Empirical_treatment/DQXq5MAu">empirical treatment</a> for most cases of uncomplicated bacterial sinusitis in children and adults when culture data is unavailable.<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> Amoxicillin is recommended as the preferred first-line treatment for <a href="/facts/Community-acquired_pneumonia/kmP37hGa">community-acquired pneumonia</a> in adults by the <a href="/facts/National_Institute_for_Health_and_Care_Excellence/83vtP8Lk">National Institute for Health and Care Excellence</a>, either alone (mild to moderate severity disease) or in combination with a <a href="/facts/Macrolide/21qIKr7a">macrolide</a>.<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> Research suggests that is as effective as <a href="/facts/Amoxicillin%2fclavulanic_acid/x19u4Lgj">co-amoxiclav</a> (a broad-spectrum antibiotic) for people admitted to hospital with pneumonia, regardless of its severity.<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a><a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> The <a href="/facts/World_Health_Organization/YNN3bgug">World Health Organization</a> (WHO) recommends amoxicillin as first-line treatment for pneumonia that is not "severe".<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> Amoxicillin is used in post-exposure inhalation of <a href="/facts/Anthrax/svk0t5G4">anthrax</a> to prevent disease progression and for prophylaxis.<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a> </p> <h3><i>H. pylori</i></h3> <p>It is effective as one part of a multi-drug regimen for the treatment of stomach infections of <i><a href="/facts/Helicobacter_pylori/9q4H68LP">Helicobacter pylori</a></i>. It is typically combined with a <a href="/facts/Proton-pump_inhibitor/JIpwabbk">proton-pump inhibitor</a> (such as <a href="/facts/Omeprazole/rJNAvWSR">omeprazole</a>) and a <a href="/facts/Macrolide_antibiotic/21qIKr7a">macrolide antibiotic</a> (such as <a href="/facts/Clarithromycin/LoeUP4Ih">clarithromycin</a>); other drug combinations are also effective.<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a> </p> <h3>Lyme borreliosis</h3> <p>Amoxicillin is effective for the treatment of early cutaneous <a href="/facts/Lyme_borreliosis/820IycaC">Lyme borreliosis</a>; the effectiveness and safety of oral amoxicillin is neither better nor worse than common alternatively-used antibiotics.<a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> </p> <h3>Odontogenic infections</h3> <p>Amoxicillin is used to treat <a href="/facts/Odontogenic_infections/00nA3xct">odontogenic infections</a>, infections of the tongue, lips, and other oral tissues. It may be prescribed following a <a href="/facts/Tooth_extraction/gfgT6bPV">tooth extraction</a>, particularly in those with <a href="/facts/Compromised_immune_system/CIEujXmc">compromised immune systems</a>.<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> </p> <h3>Skin infections</h3> <p>Amoxicillin is occasionally used for the treatment of skin infections,<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> such as <a href="/facts/Acne_vulgaris/TKJxhHSd">acne vulgaris</a>.<a class="footnote-ref" id="fnref:39" href="#fn:39"><sup>39</sup></a> It is often an effective treatment for cases of acne vulgaris that have responded poorly to other antibiotics, such as <a href="/facts/Doxycycline/A8DBTzNh">doxycycline</a> and <a href="/facts/Minocycline/naFLfSJu">minocycline</a>.<a class="footnote-ref" id="fnref:40" href="#fn:40"><sup>40</sup></a> </p> <h3>Infections in infants in resource-limited settings</h3> <p>Amoxicillin is recommended by the World Health Organization for the treatment of <a href="/facts/Infant/gaEL1QL4">infants</a> with signs and symptoms of pneumonia in resource-limited situations when the parents are unable or unwilling to accept <a href="/facts/Hospitalization/WaryeVJd">hospitalization</a> of the child. Amoxicillin in combination with <a href="/facts/Gentamicin/QXlbQH79">gentamicin</a> is recommended for the treatment of infants with signs of other severe infections when hospitalization is not an option.<a class="footnote-ref" id="fnref:41" href="#fn:41"><sup>41</sup></a> </p> <h3>Prevention of bacterial endocarditis</h3> <p>It is also used to prevent <a href="/facts/Bacterial_endocarditis/vLgg8K1V">bacterial endocarditis</a> and as a pain-reliever in high-risk people having dental work done, to prevent <i><a href="/facts/Streptococcus_pneumoniae/B5XxK27j">Streptococcus pneumoniae</a></i> and other <a href="/facts/Encapsulated_bacteria/FVSHDlXL">encapsulated bacterial</a> infections in those without <a href="/facts/Spleen/6NKn9d8s">spleens</a>, such as people with <a href="/facts/Sickle-cell_disease/93LT7ATq">sickle-cell disease</a>, and for both the prevention and the treatment of <a href="/facts/Anthrax/svk0t5G4">anthrax</a>.<a class="footnote-ref" id="fnref:42" href="#fn:42"><sup>42</sup></a> The United Kingdom recommends against its use for infectious endocarditis prophylaxis.<a class="footnote-ref" id="fnref:43" href="#fn:43"><sup>43</sup></a> These recommendations do not appear to have changed the rates of infection for infectious endocarditis.<a class="footnote-ref" id="fnref:44" href="#fn:44"><sup>44</sup></a> </p> <h3>Combination treatment</h3> <p class="note">Main article: <a href="/facts/Amoxicillin%2fclavulanic_acid/x19u4Lgj">Amoxicillin/clavulanic acid</a></p> <p>Amoxicillin is susceptible to degradation by <a href="/facts/Beta-lactamase/8PdHT21m">β-lactamase</a>-producing bacteria, which are resistant to most β-lactam antibiotics, such as <a href="/facts/Penicillin/Abo8VQ3p">penicillin</a>. For this reason, it may be combined with <a href="/facts/Clavulanic_acid/8IpvLKpm">clavulanic acid</a>, a <a href="/facts/%25CE%2592-lactamase_inhibitor/oggKG7Mu">β-lactamase inhibitor</a>. This drug combination is commonly called <a href="/facts/Coamoxiclav/x19u4Lgj">co-amoxiclav</a>.<a class="footnote-ref" id="fnref:45" href="#fn:45"><sup>45</sup></a> </p> <h3>Spectrum of activity</h3> <p>It is a <a href="/facts/Antimicrobial_spectrum/Pr4kaKkm">moderate-spectrum</a>, <a href="/facts/Bacteriolytic/th8pXeEn">bacteriolytic</a>, <a href="/facts/%25CE%2592-lactam_antibiotic/MTqEtwsg">β-lactam antibiotic</a> in the <a href="/facts/Aminopenicillin/UN3g0dme">aminopenicillin</a> family used to treat susceptible <a href="/facts/Gram-positive/H6WYQ17e">Gram-positive</a> and <a href="/facts/Gram-negative/S1PbVtp4">Gram-negative</a> bacteria. It is usually the drug of choice within the class because it is better absorbed, following oral administration, than other β-lactam antibiotics. In general, <i><a href="/facts/Streptococcus/Fx8lJ0nz">Streptococcus</a>, <a href="/facts/Bacillus_subtilis/KA8AodsE">Bacillus subtilis</a>, <a href="/facts/Enterococcus/fHlRoS0V">Enterococcus</a>, <a href="/facts/Haemophilus/uKcnj55j">Haemophilus</a>, <a href="/facts/Helicobacter/EYzbnhTU">Helicobacter</a>,</i> and <i><a href="/facts/Moraxella/2k9t8NJn">Moraxella</a></i> are susceptible to amoxicillin, whereas <i><a href="/facts/Citrobacter/unF1RAJw">Citrobacter</a>, <a href="/facts/Klebsiella/mRzCFEfA">Klebsiella</a></i> and <i><a href="/facts/Pseudomonas_aeruginosa/HBhyIxAn">Pseudomonas aeruginosa</a></i> are resistant to it.<a class="footnote-ref" id="fnref:46" href="#fn:46"><sup>46</sup></a> Some <i><a href="/facts/Escherichia_coli/nR4Gvl56">E. coli</a></i> and most clinical strains of <i><a href="/facts/Staphylococcus_aureus/9yDVBMsc">Staphylococcus aureus</a></i> have developed resistance to amoxicillin to varying degrees.<a class="footnote-ref" id="fnref:47" href="#fn:47"><sup>47</sup></a> </p> <h2 id="adverse-effects">Adverse effects</h2> <p><a href="/facts/Adverse_drug_reaction/Ea0ktF6J">Adverse effects</a> are similar to those for other <a href="/facts/%25CE%2592-lactam_antibiotic/MTqEtwsg">β-lactam antibiotics</a>, including <a href="/facts/Nausea/dyhkcbeD">nausea</a>, <a href="/facts/Vomiting/R2vQkHqV">vomiting</a>, <a href="/facts/Rash/6J8jwo8f">rashes</a>, and antibiotic-associated <a href="/facts/Colitis/vMgDVDUf">colitis</a>. <a href="/facts/Diarrhea/6TBHaRdA">Diarrhea</a> (loose bowel movements) may also occur. </p><p>Rarer adverse effects include mental and behavioral changes, <a href="/facts/Lightheadedness/Gcuruugy">lightheadedness</a>, <a href="/facts/Insomnia/C1TnQTb2">insomnia</a>, <a href="/facts/Hyperactivity/uSqjIyhd">hyperactivity</a>, <a href="/facts/Psychomotor_agitation/n1vWk6RD">agitation</a>, <a href="/facts/Mental_confusion/Pcvw6deb">confusion</a>, <a href="/facts/Anxiety/Geekl883">anxiety</a>, <a href="/facts/Sensory_overload/1hB5XWkt">sensitivity to lights and sounds</a>, and <a href="/facts/Cognitive_impairment/VhJVfJ8a">unclear thinking</a>.<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><a class="footnote-ref" id="fnref:50" href="#fn:50"><sup>50</sup></a> Immediate medical care is required upon the first signs of these adverse effects.<a class="footnote-ref" id="fnref:51" href="#fn:51"><sup>51</sup></a> Similarly to other penicillins, amoxicillin has been associated with an increased risk of <a href="/facts/Seizure/zuIrQyze">seizures</a>.<a class="footnote-ref" id="fnref:52" href="#fn:52"><sup>52</sup></a><a class="footnote-ref" id="fnref:53" href="#fn:53"><sup>53</sup></a><a class="footnote-ref" id="fnref:54" href="#fn:54"><sup>54</sup></a><a class="footnote-ref" id="fnref:55" href="#fn:55"><sup>55</sup></a> Amoxicillin-induced <a href="/facts/Neurotoxicity/FrgTICfX">neurotoxicity</a> has been especially associated with concentrations of greater than 110 mg/L.<a class="footnote-ref" id="fnref:56" href="#fn:56"><sup>56</sup></a> </p><p>The onset of an <a href="/facts/Allergic_reaction/dYAVosh8">allergic reaction</a> to amoxicillin can be very sudden and intense; emergency medical attention must be sought as quickly as possible. The initial phase of such a reaction often starts with a change in mental state, skin rash with intense itching (often beginning in the fingertips and around the groin area and rapidly spreading), and sensations of fever, nausea, and vomiting. Any other symptoms that seem even remotely suspicious must be taken very seriously. However, more mild allergy symptoms, such as a rash, can occur at any time during treatment, even up to a week after treatment has ceased. For some people allergic to amoxicillin, the adverse effects can be fatal due to <a href="/facts/Anaphylaxis/F9IDQxeL">anaphylaxis</a>.<a class="footnote-ref" id="fnref:57" href="#fn:57"><sup>57</sup></a> </p><p>Use of the amoxicillin/clavulanic acid combination for more than one week has caused a drug-induced immunoallergic-type <a href="/facts/Hepatitis/FIN87T5e">hepatitis</a> in some patients. Young children having ingested acute overdoses of amoxicillin manifested <a href="/facts/Lethargy/wJFlYuB7">lethargy</a>, vomiting, and <a href="/facts/Renal_failure/gsqb5nos">renal dysfunction</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>There is poor reporting of adverse effects of amoxicillin from clinical trials. For this reason, the severity and frequency of adverse effects from amoxicillin are probably higher than reported in clinical trials.<a class="footnote-ref" id="fnref:60" href="#fn:60"><sup>60</sup></a> </p> <h3>Nonallergic rash</h3> <p>Between 3 and 10% of children taking amoxicillin (or <a href="/facts/Ampicillin/oIodNyBw">ampicillin</a>) show a late-developing (>72 hours after beginning medication and having never taken penicillin-like medication previously) rash, which is sometimes referred to as the "amoxicillin rash". The rash can also occur in adults and may rarely be a component of the <a href="/facts/DRESS_syndrome/UnHsEbv0">DRESS syndrome</a>.<a class="footnote-ref" id="fnref:61" href="#fn:61"><sup>61</sup></a> </p><p>The rash is described as <a href="/facts/Maculopapular/YAIQGkbB">maculopapular</a> or morbilliform (<a href="/facts/Measles/tepQCUIG">measles-like</a>; therefore, in medical literature, it is called "amoxicillin-induced morbilliform rash".<a class="footnote-ref" id="fnref:62" href="#fn:62"><sup>62</sup></a>). It starts on the trunk and can spread from there. This rash is unlikely to be a true allergic reaction and is not a contraindication for future amoxicillin usage, nor should the current regimen necessarily be stopped. However, this common amoxicillin rash and a dangerous allergic reaction cannot easily be distinguished by inexperienced persons, so a healthcare professional is often required to distinguish between the two.<a class="footnote-ref" id="fnref:63" href="#fn:63"><sup>63</sup></a><a class="footnote-ref" id="fnref:64" href="#fn:64"><sup>64</sup></a> </p><p>A nonallergic amoxicillin rash may also be an indicator of <a href="/facts/Infectious_mononucleosis/pTwDw4VF">infectious mononucleosis</a>. Some studies indicate about 80–90% of patients with acute <a href="/facts/Epstein%25E2%2580%2593Barr_virus/Uv8f1PNd">Epstein–Barr virus</a> infection treated with amoxicillin or ampicillin develop such a rash.<a class="footnote-ref" id="fnref:65" href="#fn:65"><sup>65</sup></a> </p> <h2 id="interactions">Interactions</h2> <p>Amoxicillin may interact with these drugs: </p> <ul><li><a href="/facts/Anticoagulants/cARpjm0G">Anticoagulants</a> (<a href="/facts/Dabigatran/qEzkkvr4">dabigatran</a>, <a href="/facts/Warfarin/kMnH6tb0">warfarin</a>).<a class="footnote-ref" id="fnref:66" href="#fn:66"><sup>66</sup></a><a class="footnote-ref" id="fnref:67" href="#fn:67"><sup>67</sup></a><a class="footnote-ref" id="fnref:68" href="#fn:68"><sup>68</sup></a><a class="footnote-ref" id="fnref:69" href="#fn:69"><sup>69</sup></a></li> <li><a href="/facts/Methotrexate/LoDvhRKX">Methotrexate</a> (<a href="/facts/Chemotherapy/fWTLbaUT">chemotherapy</a> and <a href="/facts/Immunosuppressant/ctlB3Hda">immunosuppressant</a>).<a class="footnote-ref" id="fnref:70" href="#fn:70"><sup>70</sup></a><a class="footnote-ref" id="fnref:71" href="#fn:71"><sup>71</sup></a></li> <li><a href="/facts/Typhoid_vaccine/PWs2g8uB">Typhoid</a>, <a href="/facts/Cholera_vaccine/hW6PBKmt">Cholera</a> and <a href="/facts/BCG_vaccine/1hG40pC8">BCG</a> vaccines.<a class="footnote-ref" id="fnref:72" href="#fn:72"><sup>72</sup></a><a class="footnote-ref" id="fnref:73" href="#fn:73"><sup>73</sup></a></li> <li><a href="/facts/Probenecid/bCAH0sqh">Probenecid</a> reduces renal excretion and increases blood levels of amoxicillin.<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></li> <li><a href="/facts/Oral_contraceptives/QfDgVrGA">Oral contraceptives</a> potentially become less effective.<a class="footnote-ref" id="fnref:76" href="#fn:76"><sup>76</sup></a></li> <li><a href="/facts/Allopurinol/uTKf79Yr">Allopurinol</a> (<a href="/facts/Gout/ktWD69YP">gout</a> treatment).<a class="footnote-ref" id="fnref:77" href="#fn:77"><sup>77</sup></a><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></li> <li><a href="/facts/Mycophenolic_acid/kHpk0USt">Mycophenolate</a> (immunosuppressant)<a class="footnote-ref" id="fnref:80" href="#fn:80"><sup>80</sup></a></li></ul> <p>When given intravenously or intramuscularly:<a class="footnote-ref" id="fnref:81" href="#fn:81"><sup>81</sup></a> </p> <ul><li>It should not be mixed with blood products, or <a href="/facts/Proteinaceous/Jxmagu3E">proteinaceous</a> fluids (including protein <a href="/facts/Hydrolysates/NYIGlHAu">hydrolysates</a>) or with intravenous lipid emulsions</li> <li><a href="/facts/Aminoglycoside/eNQrtDg0">aminoglycoside</a> should be injected at a separate site from amoxicillin if the patient is prescribed both medications at the same time. Neither drug should be mixed in a syringe. Neither should they be mixed in an intravenous fluid container or giving set because of loss of activity of the aminoglycoside under these conditions.</li> <li><a href="/facts/Ciprofloxacin/RNAy8SHB">ciprofloxacin</a> should not be mixed with amoxicillin.</li> <li>Infusions containing <a href="/facts/Dextran/SwRxlR4A">dextran</a> or <a href="/facts/Bicarbonate/zzSVVAl1">bicarbonate</a> should not be mixed with amoxicillin solutions.</li></ul> <h2 id="pharmacology">Pharmacology</h2> <p>Amoxicillin (α-amino-<i>p</i>-hydroxybenzyl penicillin) is a semisynthetic derivative of penicillin with a structure similar to ampicillin but with better absorption when taken by mouth, thus yielding higher concentrations in blood and in urine.<a class="footnote-ref" id="fnref:82" href="#fn:82"><sup>82</sup></a> Amoxicillin diffuses easily into tissues and body fluids. It will cross the <a href="/facts/Placenta/7XUoks1b">placenta</a> and is excreted into <a href="/facts/Breastmilk/wVfKCjyw">breastmilk</a> in small quantities. It is metabolized by the liver and excreted into the urine. It has an onset of 30 minutes and a <a href="/facts/Biological_half-life/7nB2JtMr">half-life</a> of 3.7 hours in newborns and 1.4 hours in adults.<a class="footnote-ref" id="fnref:83" href="#fn:83"><sup>83</sup></a> </p><p>Amoxicillin attaches to the <a href="/facts/Cell_wall/DYXJVrnw">cell wall</a> of susceptible bacteria and results in their death. It is effective against streptococci, pneumococci, enterococci, <i><a href="/facts/Haemophilus_influenzae/wqIpoDI1">Haemophilus influenzae</a></i>, <i>Escherichia coli</i>, <i><a href="/facts/Proteus_mirabilis/awwMoQdt">Proteus mirabilis</a></i>, <i><a href="/facts/Neisseria_meningitidis/u4SqwHuc">Neisseria meningitidis</a></i>, <i><a href="/facts/Neisseria_gonorrhoeae/2oq5rccN">Neisseria gonorrhoeae</a></i>, <i><a href="/facts/Shigella/xKEXoT4w">Shigella</a></i>, <i><a href="/facts/Chlamydia_trachomatis/54QHKFWC">Chlamydia trachomatis</a></i>, <i>Salmonella</i>, <i><a href="/facts/Borrelia_burgdorferi/sSvh5CyA">Borrelia burgdorferi</a></i>, and <i>Helicobacter pylori</i>.<a class="footnote-ref" id="fnref:84" href="#fn:84"><sup>84</sup></a> As a derivative of <a href="/facts/Ampicillin/oIodNyBw">ampicillin</a>, amoxicillin is a member of the <a href="/facts/Penicillin/Abo8VQ3p">penicillin</a> family and, like penicillins, is a <a href="/facts/%25CE%2592-lactam_antibiotic/MTqEtwsg">β-lactam antibiotic</a>.<a class="footnote-ref" id="fnref:85" href="#fn:85"><sup>85</sup></a> It inhibits <a href="/facts/Cross-link/zeQ9hEAA">cross-linkage</a> between the linear <a href="/facts/Peptidoglycan/lflRRUNw">peptidoglycan</a> polymer chains that make up a major component of the bacterial <a href="/facts/Cell_wall/DYXJVrnw">cell wall</a>. It has two <a href="/facts/Ionizable/W13Ceavd">ionizable</a> groups in the physiological range (the <a href="/facts/Amino_group/SN7W44fv">amino group</a> in alpha-position to the <a href="/facts/Amide/C6kCzYEA">amide</a> <a href="/facts/Carbonyl_group/KJ71bo3X">carbonyl group</a> and the <a href="/facts/Carboxyl_group/U4xuMosy">carboxyl group</a>).<a class="footnote-ref" id="fnref:86" href="#fn:86"><sup>86</sup></a> </p> <h2 id="chemistry">Chemistry</h2> <p>Amoxicillin is a <a href="/facts/%25CE%2592-lactam/jasUACD2">β-lactam</a> and <a href="/facts/Aminopenicillin/UN3g0dme">aminopenicillin</a> <a href="/facts/Antibiotic/sF1kIfxg">antibiotic</a> in terms of <a href="/facts/Chemical_structure/r5rT1Lj4">chemical structure</a>.<a class="footnote-ref" id="fnref:87" href="#fn:87"><sup>87</sup></a><a class="footnote-ref" id="fnref:88" href="#fn:88"><sup>88</sup></a> It is <a href="/facts/Structural_analog/3aysWSVG">structurally related</a> to <a href="/facts/Ampicillin/oIodNyBw">ampicillin</a>.<a class="footnote-ref" id="fnref:89" href="#fn:89"><sup>89</sup></a><a class="footnote-ref" id="fnref:90" href="#fn:90"><sup>90</sup></a> </p><p>The experimental <a href="/facts/Partition_coefficient/D4aTlBal">log P</a> of amoxicillin is 0.87.<a class="footnote-ref" id="fnref:91" href="#fn:91"><sup>91</sup></a><a class="footnote-ref" id="fnref:92" href="#fn:92"><sup>92</sup></a> It is described as an "ambiphilic"—between <a href="/facts/Hydrophilic/k8p95WYu">hydrophilic</a> and <a href="/facts/Lipophilic/AWpsR8Xe">lipophilic</a>—antibiotic.<a class="footnote-ref" id="fnref:93" href="#fn:93"><sup>93</sup></a> </p> <h2 id="history">History</h2> <p class="note">See also: <a href="/facts/Timeline_of_antibiotics/WXMhnNYq">Timeline of antibiotics</a></p> <p>Amoxicillin was one of several <a href="/facts/Semisynthesis/nEMoPxhv">semisynthetic</a> derivatives of 6-aminopenicillanic acid (<a href="/facts/6-APA/fQXXYpyn">6-APA</a>) developed by the <a href="/facts/Beecham_Group/SN7wXHx9">Beecham Group</a> in the 1960s. It was invented by Anthony Alfred Walter Long and John Herbert Charles Nayler, two British scientists.<a class="footnote-ref" id="fnref:94" href="#fn:94"><sup>94</sup></a><a class="footnote-ref" id="fnref:95" href="#fn:95"><sup>95</sup></a> It became available in 1972 and was the second <a href="/facts/Aminopenicillin/UN3g0dme">aminopenicillin</a> to reach the market (after <a href="/facts/Ampicillin/oIodNyBw">ampicillin</a> in 1961).<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><a class="footnote-ref" id="fnref:98" href="#fn:98"><sup>98</sup></a> <a href="/facts/Coamoxiclav/x19u4Lgj">Co-amoxiclav</a> became available in 1981.<a class="footnote-ref" id="fnref:99" href="#fn:99"><sup>99</sup></a> </p> <h2 id="society-and-culture">Society and culture</h2> <h3>Economics</h3> <p>Amoxicillin is relatively inexpensive.<a class="footnote-ref" id="fnref:100" href="#fn:100"><sup>100</sup></a> In 2022, a survey of eight generic antibiotics commonly prescribed in the United States found their average cost to be about $42.67, while amoxicillin was sold for $12.14 on average.<a class="footnote-ref" id="fnref:101" href="#fn:101"><sup>101</sup></a> </p> <h3>Modes of delivery</h3> <p>Pharmaceutical manufacturers make amoxicillin in tri<a href="/facts/Hydrate/dev82l69">hydrate</a> form, for oral use available as <a href="/facts/Capsule_(pharmacy)/cVSWhU1m">capsules</a>, regular, chewable and dispersible <a href="/facts/Tablet_(pharmacy)/PcYmnjd0">tablets</a>, syrup and <a href="/facts/Pediatric/hnkMfLeg">pediatric</a> <a href="/facts/Suspension_(chemistry)/S3xp96TL">suspension</a> for oral use, and as the sodium salt for <a href="/facts/Intravenous/AwwuD3Nu">intravenous</a> administration.[<i>medical citation needed</i>] </p><p>An <a href="/facts/Extended-release/YpWevExQ">extended-release</a> is available.<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> The intravenous form of amoxicillin is not sold in the United States.<a class="footnote-ref" id="fnref:104" href="#fn:104"><sup>104</sup></a> When an intravenous aminopenicillin is required in the United States, ampicillin is typically used. When there is an adequate response to ampicillin, the course of antibiotic therapy may often be completed with oral amoxicillin.<a class="footnote-ref" id="fnref:105" href="#fn:105"><sup>105</sup></a> </p><p>Research with mice indicated successful delivery using <a href="/facts/Intraperitoneally/AwQIlxSb">intraperitoneally</a> injected amoxicillin-bearing <a href="/facts/Microparticles/bYKcPY7F">microparticles</a>.<a class="footnote-ref" id="fnref:106" href="#fn:106"><sup>106</sup></a> </p> <h3>Names</h3> <p>Amoxicillin is the <a href="/facts/International_nonproprietary_name/wYL655x6">international nonproprietary name</a> (INN),<a class="footnote-ref" id="fnref:107" href="#fn:107"><sup>107</sup></a> <a href="/facts/British_Approved_Name/pm1t52SQ">British Approved Name</a> (BAN), and <a href="/facts/United_States_Adopted_Name/5AFEKGfQ">United States Adopted Name</a> (USAN), while amoxycillin is the <a href="/facts/Australian_Approved_Name/lLXrcJ5F">Australian Approved Name</a> (AAN). </p><p>Amoxicillin is one of the semisynthetic penicillins discovered by the former pharmaceutical company <a href="/facts/Beecham_Group/SN7wXHx9">Beecham Group</a>. The patent for amoxicillin has expired, thus amoxicillin and co-amoxiclav preparations are marketed under various brand names across the world.<a class="footnote-ref" id="fnref:108" href="#fn:108"><sup>108</sup></a> </p> <h2 id="veterinary-uses">Veterinary uses</h2> <p>Amoxicillin is also sometimes used as an <a href="/facts/Antibiotic_use_in_livestock/NzwPDrK5">antibiotic for animals</a>. The use of amoxicillin for animals intended for human consumption (<a href="/facts/Chicken/RD2eTd83">chickens</a>, <a href="/facts/Cattle/44qV9B6S">cattle</a>, and <a href="/facts/Swine/7SE0mdWz">swine</a> for example) has been approved.<a class="footnote-ref" id="fnref:109" href="#fn:109"><sup>109</sup></a> </p> <h2 id="further-reading">Further reading</h2> <ul><li>Neal MJ (2002). <i>Medical Pharmacology at a Glance</i> (4th ed.). 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Retrieved 8 April 2012. <a href="https://web.archive.org/web/20181222141136/http://www.toku-e.com/Assets/MIC/Amoxicillin%20sodium%20salt.pdf" target="_blank">https://web.archive.org/web/20181222141136/http://www.toku-e.com/Assets/MIC/Amoxicillin%20sodium%20salt.pdf</a> <a href="#fnref:46" class="footnote-back-ref">↩</a></p></li> <li id="fn:47"><p>Tadesse BT, Ashley EA, Ongarello S, Havumaki J, Wijegoonewardena M, González IJ, et al. (September 2017). "Antimicrobial resistance in Africa: a systematic review". BMC Infectious Diseases. 17 (1): 616. doi:10.1186/s12879-017-2713-1. PMC 5594539. PMID 28893183. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5594539" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5594539</a> <a href="#fnref:47" class="footnote-back-ref">↩</a></p></li> <li id="fn:48"><p>"Amoxil (amoxicillin) Capsules, Tablets, Chewable Tablets, and Powder for Oral Suspension". DailyMed. Archived from the original on 9 October 2022. Retrieved 8 October 2022. Central Nervous System: Reversible hyperactivity, agitation, anxiety, insomnia, confusion, convulsions, behavioral changes, and/or dizziness have been reported rarely. <a href="https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=49302" target="_blank">https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=49302</a> <a href="#fnref:48" class="footnote-back-ref">↩</a></p></li> <li id="fn:49"><p>Esposito S, Canevini MP, Principi N (July 2017). "Complications associated with antibiotic administration: neurological adverse events and interference with antiepileptic drugs". Int J Antimicrob Agents. 50 (1): 1–8. doi:10.1016/j.ijantimicag.2017.01.027. PMID 28414069. Benzylpenicillin, the most neurotoxic among the penicillins, has often been associated with the development of encephalopathy and seizures both in animals and humans [21], [22]. 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