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Imidazopyridine
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<h2 id="sedatives">Sedatives</h2> <p>Anxiolytics, sedatives and hypnotics (<a href="/facts/GABAA_receptor_positive_allosteric_modulator/trahTF7m">GABAA receptor positive allosteric modulators</a>): </p> <ul><li>Imidazo[1,2-a]pyridines: <ul><li><a href="/facts/Alpidem/EuMb4tm3">Alpidem</a> (original brand name Ananxyl)—an <a href="/facts/Anxiolytic/uEWpGca9">anxiolytic</a> that was withdrawn from the market worldwide in 1995 due to <a href="/facts/Hepatotoxicity/xbLcKPNG">hepatotoxicity</a>.</li> <li><a href="/facts/DS-1_(drug)/P0nUYumQ">DS-1</a>—a <a href="/facts/GABAA_receptor/6G4rAGb3">GABAA receptor</a> positive <a href="/facts/Allosteric_modulator/Gg1It5Cj">allosteric modulator</a> selective for the <a href="/facts/GABRA4/fdySU0yy">α4</a><a href="/facts/GABRB3/wyKS60WS">β3</a><a href="/facts/GABRD/9687tuu0">δ</a> subtype, which is not targeted by other GABAergics such as <a href="/facts/Benzodiazepine/IgbJr4jy">benzodiazepines</a> or other <a href="/facts/Nonbenzodiazepine/cXPFEcM8">nonbenzodiazepines</a>.<a class="footnote-ref" id="fnref:1" href="#fn:1"><sup>1</sup></a></li> <li><a href="/facts/Necopidem/l2YnlE1h">Necopidem</a>—an anxiolytic. It has not found clinical use.</li> <li><a href="/facts/Saripidem/5l9qACN7">Saripidem</a>—a <a href="/facts/Sedative/JWzvq66P">sedative</a> and <a href="/facts/Anxiolytic/uEWpGca9">anxiolytic</a>. It is not used clinically.</li> <li><a href="/facts/TP-003/Gozn2flv">TP-003</a>—a subtype-selective <a href="/facts/Partial_agonist/VLm2vmgU">partial agonist</a> at <a href="/facts/GABA_A_receptor/6G4rAGb3">GABAA receptors</a>, binding to GABAA receptor complexes bearing either <a href="/facts/GABRA2/6tRS5u3k">α2</a>, <a href="/facts/GABRA3/UhVxE0Sy">α3</a> or <a href="/facts/GABRA5/1W1Cne1d">α5</a> subunits, but only showing significant efficacy at α3.</li> <li><a href="/facts/Zolpidem/mkFaPJV7">Zolpidem</a> (original brand name Ambien)—a widely used <a href="/facts/Hypnotic/0SBVYkMe">hypnotic</a>. Generic versions are widely available.</li></ul></li> <li>Imidazo[4,5-c]pyridines: <ul><li><a href="/facts/Bamaluzole/5zkDUly0">Bamaluzole</a>—a <a href="/facts/GABAA_receptor/6G4rAGb3">GABAA receptor</a>-agonizing <a href="/facts/Anticonvulsant/uR8cxJbj">anticonvulsant</a> that was never marketed.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a></li></ul></li></ul> <h2 id="antipsychotic">Antipsychotic</h2> <p><a href="/facts/Antipsychotic/7bNTg7T3">Antipsychotics</a>: </p> <ul><li>Imidazo[1,2-a]pyridines: <ul><li><a href="/facts/Mosapramine/zdcnGm0x">Mosapramine</a> (brand name クレミン, Cremin)—an <a href="/facts/Atypical_antipsychotic/PQYUYXMu">atypical antipsychotic</a> used in Japan.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a></li></ul></li></ul> <h2 id="gastrointestinal">Gastrointestinal</h2> <p>Drugs used for <a href="/facts/Peptic_ulcer/peMGnYCd">peptic ulcer disease (PUD)</a>, <a href="/facts/Gastroesophageal_reflux_disease/8YhncnDz">GERD</a> and <a href="/facts/Prokinetic_agent/1UWsrM0h">gastroprokinetic agents</a> (motility stimulants): </p> <ul><li>Imidazo[1,2-a]pyridines: <ul><li><a href="/facts/CJ-033466/CHaXfzJJ">CJ-033466</a>—an experimental gastroprokinetic acting as a selective <a href="/facts/5-HT4_receptor/aFSHbN6U">5-HT4 serotonin receptor</a> partial agonist.<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a></li> <li><a href="/facts/Zolimidine/MqAAuUcy">Zolimidine</a>—a gastroprotective agent.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a></li> <li><a href="/facts/Linaprazan/3QEgCpJ0">Linaprazan</a>—a <a href="/facts/Discovery_and_development_of_proton_pump_inhibitors/1DUwJe2R">potassium-competitive acid blocker</a> which demonstrated similar efficacy as <a href="/facts/Esomeprazole/ogcBGRYX">esomeprazole</a> in healing and controlling symptoms of GERD patients with erosive esophagitis.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a></li> <li>SCH28080—the prototypical potassium-competitive acid blocker which has not found clinical use because of liver toxicity in animal trials and elevated liver enzyme activity in the serum of human volunteers.<a class="footnote-ref" id="fnref:7" href="#fn:7"><sup>7</sup></a></li></ul></li> <li>Imidazo[4,5-b]pyridines: <ul><li><a href="/facts/Tenatoprazole/BaUC6nvS">Tenatoprazole</a>—it blocks the gastric <a href="/facts/Hydrogen_potassium_ATPase/8fbvtrRP">proton pump</a> leading to decline of <a href="/facts/Gastric_acid/btVCyhYH">gastric acid</a> production.</li></ul></li></ul> <h2 id="anti-inflammatories">Anti-inflammatories</h2> <p><a href="/facts/Nonsteroidal_anti-inflammatory_drug/coIkzl4s">NSAIDs</a>, <a href="/facts/Analgesics/xLj4XBcq">analgesics</a> and <a href="/facts/Antimigraine/bz43mSYn">antimigraine</a> drugs: </p> <ul><li>Imidazo[1,2-a]pyridines: <ul><li><a href="/facts/Miroprofen/xB6x0s5T">Miroprofen</a>—a derivative of <a href="/facts/Propionic_acid/ugBEw0Ia">propionic acid</a>.</li></ul></li> <li>Imidazo[4,5-b]pyridines: <ul><li><a href="/facts/Telcagepant/TPotLAk0">Telcagepant</a>—a <a href="/facts/Calcitonin_gene-related_peptide_receptor_antagonist/fg12vmUj">calcitonin gene-related peptide receptor antagonist</a> which was in clinical trials as a remedy for <a href="/facts/Migraine/5XaE1W25">migraine</a>. Its development was terminated.<a class="footnote-ref" id="fnref:8" href="#fn:8"><sup>8</sup></a></li></ul></li></ul> <h2 id="cardiovascular">Cardiovascular</h2> <p>Drugs acting on the <a href="/facts/Cardiovascular_system/WXwudzzc">cardiovascular system</a>: </p> <ul><li>Imidazo[1,2-a]pyridines: <ul><li><a href="/facts/Olprinone/228mAAub">Olprinone</a> (loprinone)—a <a href="/facts/Cardiac_stimulant/ds2xIzLf">cardiac stimulant</a>.<a class="footnote-ref" id="fnref:9" href="#fn:9"><sup>9</sup></a></li></ul></li></ul> <h2 id="bone">Bone</h2> <p>Drugs for treatment of <a href="/facts/Bone_disease/FfttXmMv">bone diseases</a>: </p> <ul><li>Imidazo[1,2-a]pyridines: <ul><li><a href="/facts/Minodronic_acid/EDlrClPK">Minodronic acid</a> (brand names Bonoteo, Recalbon)—a third-generation <a href="/facts/Bisphosphonate/s6po5jLd">bisphosphonate</a> used for the treatment of osteoporosis.<a class="footnote-ref" id="fnref:10" href="#fn:10"><sup>10</sup></a></li></ul></li></ul> <h2 id="antineoplastic">Antineoplastic</h2> <p><a href="/facts/Antineoplastic/fWTLbaUT">Antineoplastic</a> agents: </p> <ul><li>Imidazo[1,5-a]pyridines: <ul><li><a href="/facts/Fadrozole/nmSIYVnj">Fadrozole</a> (brand name Afema)—an <a href="/facts/Aromatase/MMXTK90e">aromatase</a> inhibitor.</li></ul></li> <li>Imidazo[4,5-c]pyridines: <ul><li><a href="/facts/3-Deazaneplanocin_A/eRjAXlSM">3-Deazaneplanocin A</a>—an <a href="/facts/S-Adenosyl-L-homocysteine/qejSLwMv"><i>S</i>-adenosyl-L-homocysteine</a> synthesis inhibitor and <a href="/facts/Histone_methyltransferase/bbCDPmlz">histone methyltransferase</a> <a href="/facts/EZH2/tU93NsJG">EZH2</a> inhibitor.</li></ul></li></ul> <h2 id="antiviral">Antiviral</h2> <p>Directly-acting <a href="/facts/Antiviral_drug/Xgbd2eI2">antiviral agents</a>: </p> <ul><li>Imidazo[1,2-a]pyridines: <ul><li>Tegobuvir (GS-9190) - an <a href="/facts/Allosteric_regulation/alMRuyt9">allosteric</a>, non-<a href="/facts/Nucleoside/G40crf0F">nucleoside</a> <a href="/facts/Hepacivirus_C/DFUwAzlB">hepatitis C virus</a> <a href="/facts/NS5B/QupCdRUa">NS5B</a> <a href="/facts/RNA-dependent_RNA_polymerase/UgPn4rjz">RNA-dependent RNA polymerase</a> inhibitor targeting the thumb II allosteric site.<a class="footnote-ref" id="fnref:11" href="#fn:11"><sup>11</sup></a></li></ul></li></ul> <h2 id="daergic">DAergic</h2> <ul><li>PIP3EA [885446-91-3] <a href="/facts/Dopamine_receptor_D4/26otIqul">D4 agonist</a>, shown to induce penile erection in rats.<a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a></li></ul> <h2 id="external-links">External links</h2> <ul><li> Media related to Imidazopyridines at Wikimedia Commons</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Wafford KA, van Niel MB, Ma QP, Horridge E, Herd MB, Peden DR, et al. (January 2009). "Novel compounds selectively enhance delta subunit containing GABA A receptors and increase tonic currents in thalamus". Neuropharmacology. 56 (1): 182–9. doi:10.1016/j.neuropharm.2008.08.004. PMID 18762200. S2CID 207224202. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9. <a href="0-412-46630-9" target="_blank">0-412-46630-9</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Takahashi N, Terao T, Oga T, Okada M (1999). "Comparison of risperidone and mosapramine addition to neuroleptic treatment in chronic schizophrenia". Neuropsychobiology. 39 (2): 81–5. doi:10.1159/000026565. PMID 10072664. S2CID 6554048. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Mikami T, Ochi Y, Suzuki K, Saito T, Sugie Y, Sakakibara M (April 2008). "5-Amino-6-chloro-N-[(1-isobutylpiperidin-4-yl)methyl]-2-methylimidazo[1,2-alpha]pyridine-8-carboxamide (CJ-033,466), a novel and selective 5-hydroxytryptamine4 receptor partial agonist: pharmacological profile in vitro and gastroprokinetic effect in conscious dogs". The Journal of Pharmacology and Experimental Therapeutics. 325 (1): 190–9. doi:10.1124/jpet.107.133850. PMID 18198343. S2CID 40500864. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Belohlavek D, Malfertheiner P (1979). "The effect of zolimidine, imidazopyridine-derivate, on the duodenal ulcer healing". Scandinavian Journal of Gastroenterology. Supplement. 54: 44. PMID 161649. <a href="/wiki/PMID_(identifier)" target="_blank">/wiki/PMID_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Kahrilas PJ, Dent J, Lauritsen K, Malfertheiner P, Denison H, Franzén S, Hasselgren G (December 2007). "A randomized, comparative study of three doses of AZD0865 and esomeprazole for healing of reflux esophagitis". Clinical Gastroenterology and Hepatology. 5 (12): 1385–91. doi:10.1016/j.cgh.2007.08.014. PMID 17950677. <a href="https://doi.org/10.1016%2Fj.cgh.2007.08.014" target="_blank">https://doi.org/10.1016%2Fj.cgh.2007.08.014</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>Ravinder Reddy S, Basavaraja HS, Shivaprasad S. "Reversible Proton Pump Inhibitors: A Superior Edge — Features". Pharmabiz.com. Saffron Media Pvt. Ltd I. Archived from the original on 5 March 2016. Retrieved 7 December 2015. <a href="https://web.archive.org/web/20160305125148/http://www.pharmabiz.com/article/detnews.asp?articleid=21265§ionid=46" target="_blank">https://web.archive.org/web/20160305125148/http://www.pharmabiz.com/article/detnews.asp?articleid=21265§ionid=46</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>"Merck Announces Second Quarter 2011 Financial Results". Archived from the original on 12 April 2013. Retrieved 6 December 2015. <a href="https://web.archive.org/web/20130412063354/http://www.mercknewsroom.com/press-release/financial-news/merck-announces-second-quarter-2011-financial-results" target="_blank">https://web.archive.org/web/20130412063354/http://www.mercknewsroom.com/press-release/financial-news/merck-announces-second-quarter-2011-financial-results</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>Uemura Y, Tanaka S, Ida S, Yuzuriha T (December 1993). "Pharmacokinetic study of loprinone hydrochloride, a new cardiotonic agent, in beagle dogs". The Journal of Pharmacy and Pharmacology. 45 (12): 1077–81. doi:10.1111/j.2042-7158.1993.tb07184.x. PMID 7908977. S2CID 39583447. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Hegde S, Schmidt M (January 2010). "To market, to market—2009". Annual Reports in Medicinal Chemistry. 45: 466–537. doi:10.1016/s0065-7743(10)45028-9. ISBN 9780123809025. <a href="9780123809025" target="_blank">9780123809025</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>Hebner CM, Han B, Brendza KM, Nash M, Sulfab M, Tian Y, et al. (2012). "The HCV non-nucleoside inhibitor Tegobuvir utilizes a novel mechanism of action to inhibit NS5B polymerase function". PLOS ONE. 7 (6): e39163. Bibcode:2012PLoSO...739163H. doi:10.1371/journal.pone.0039163. PMC 3374789. PMID 22720059. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3374789" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3374789</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>Melis, Maria Rosaria; Succu, Salvatora; Sanna, Fabrizio; Melis, Tiziana; Mascia, Maria Stefania; Enguehard‐Gueiffier, Cécile; Hubner, Harald; Gmeiner, Peter; Gueiffier, Alain; Argiolas, Antonio (2006). "PIP3EA and PD‐168077, two selective dopamine D4 receptor agonists, induce penile erection in male rats: site and mechanism of action in the brain". European Journal of Neuroscience. 24 (7): 2021–2030. doi:10.1111/j.1460-9568.2006.05043.x. ISSN 0953-816X. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> </ol>