Mosapride

{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 462255663 | IUPAC_name = 4-Amino-5-chloro-2-ethoxy-''N''-<nowiki>[[</nowiki>4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl]benzamide | image = Mosapride.svg | image_class = skin-invert-image | width = 260 | image2 = 3D Mosapride.png | image_class2 = bg-transparent

| tradename = | Drugs.com = {{drugs.com|international|mosapride}} | pregnancy_AU =  | pregnancy_US =  | pregnancy_category = | legal_AU =  | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration =

| CAS_number_Ref = {{cascite|changed|??}} | CAS_number = 112885-41-3 | ATC_prefix = A03 | ATC_suffix = FA09 | PubChem = 119584 | ChEBI = 94373 | IUPHAR_ligand = 242 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB11675 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 106780 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = I8MFJ1C0BY | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D08236 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 60889

| C=21 | H=25 | Cl=1 | F=1 | N=3 | O=3 | smiles = Clc1cc(c(OCC)cc1N)C(=O)NCC3OCCN(Cc2ccc(F)cc2)C3 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C21H25ClFN3O3/c1-2-28-20-10-19(24)18(22)9-17(20)21(27)25-11-16-13-26(7-8-29-16)12-14-3-5-15(23)6-4-14/h3-6,9-10,16H,2,7-8,11-13,24H2,1H3,(H,25,27) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = YPELFRMCRYSPKZ-UHFFFAOYSA-N | synonyms = }}

'''Mosapride''' is a gastroprokinetic agent that acts as a selective 5HT4 agonist. The major active metabolite of mosapride, known as M1, additionally acts as a 5HT3 antagonist,<ref name="Tack-2012">{{cite journal | vauthors = Tack J, Camilleri M, Chang L, Chey WD, Galligan JJ, Lacy BE, Müller-Lissner S, Quigley EM, Schuurkes J, De Maeyer JH, Stanghellini V | display-authors = 6 | title = Systematic review: cardiovascular safety profile of 5-HT(4) agonists developed for gastrointestinal disorders | journal = Alimentary Pharmacology & Therapeutics | volume = 35 | issue = 7 | pages = 745–67 | date = April 2012 | pmid = 22356640 | pmc = 3491670 | doi = 10.1111/j.1365-2036.2012.05011.x }}</ref> which accelerates emptying throughout the whole of the gastrointestinal tract in humans,<ref name="pmid16898619">{{cite journal | vauthors = Odaka T, Suzuki T, Seza A, Yamaguchi T, Saisho H | title = [Serotonin 5- HT4 receptor agonist (mosapride citrate)] | language = ja | journal = Nihon Rinsho. Japanese Journal of Clinical Medicine | volume = 64 | issue = 8 | pages = 1491–4 | date = August 2006 | pmid = 16898619 }}</ref> and is used for the treatment of gastritis, gastroesophageal reflux disease, functional dyspepsia<ref name="pmid18457463">{{cite journal | vauthors = Curran MP, Robinson DM | title = Mosapride in gastrointestinal disorders | journal = Drugs | volume = 68 | issue = 7 | pages = 981–91 | year = 2008 | pmid = 18457463 | doi = 10.2165/00003495-200868070-00007 | s2cid = 195686202 }}</ref> and irritable bowel syndrome.<ref>{{cite journal | vauthors = Mizuta Y, Shikuwa S, Isomoto H, Mishima R, Akazawa Y, Masuda J, Omagari K, Takeshima F, Kohno S | display-authors = 6 | title = Recent insights into digestive motility in functional dyspepsia | journal = Journal of Gastroenterology | volume = 41 | issue = 11 | pages = 1025–40 | date = November 2006 | pmid = 17160514 | doi = 10.1007/s00535-006-1966-z | s2cid = 13353302 }}</ref> It is recommended to be taken on an empty stomach (i.e. at least one hour before food or two hours after food).<ref>{{cite journal | vauthors = Kato S, Morie T, Yoshida N | title = Synthesis and biological activities of metabolites of mosapride, a new gastroprokinetic agent | journal = Chemical & Pharmaceutical Bulletin | volume = 43 | issue = 4 | pages = 699–702 | date = April 1995 | pmid = 7600620 | doi = 10.1248/cpb.43.699 | doi-access = free }}</ref>

In addition to its prokinetic properties, mosapride also exerts anti-inflammatory effects on the gastrointestinal tract which may contribute to some of its therapeutic effects.<ref name="pmid21115544">{{cite journal | vauthors = Tsuchida Y, Hatao F, Fujisawa M, Murata T, Kaminishi M, Seto Y, Hori M, Ozaki H | display-authors = 6 | title = Neuronal stimulation with 5-hydroxytryptamine 4 receptor induces anti-inflammatory actions via α7nACh receptors on muscularis macrophages associated with postoperative ileus | journal = Gut | volume = 60 | issue = 5 | pages = 638–47 | date = May 2011 | pmid = 21115544 | pmc = 3071096 | doi = 10.1136/gut.2010.227546 }}</ref> Mosapride also promotes neurogenesis in the gastrointestinal tract which may prove useful in certain bowel disorders.<ref name="pmid22194416">{{cite journal | vauthors = Kawahara I, Kuniyasu H, Matsuyoshi H, Goto K, Obata K, Misawa H, Fujii H, Takaki M | display-authors = 6 | title = Comparison of effects of a selective 5-HT reuptake inhibitor versus a 5-HT4 receptor agonist on in vivo neurogenesis at the rectal anastomosis in rats | journal = American Journal of Physiology. Gastrointestinal and Liver Physiology | volume = 302 | issue = 6 | pages = G588-97 | date = March 2012 | pmid = 22194416 | doi = 10.1152/ajpgi.00284.2011 | hdl = 10564/2701 | hdl-access = free }}</ref><ref name="pmid20146727">{{cite journal | vauthors = Matsuyoshi H, Kuniyasu H, Okumura M, Misawa H, Katsui R, Zhang GX, Obata K, Takaki M | display-authors = 6 | title = A 5-HT(4)-receptor activation-induced neural plasticity enhances in vivo reconstructs of enteric nerve circuit insult | journal = Neurogastroenterology and Motility | volume = 22 | issue = 7 | pages = 806–13, e226 | date = July 2010 | pmid = 20146727 | doi = 10.1111/j.1365-2982.2010.01474.x | s2cid = 36819102 }}</ref> The neurogenesis is due to mosapride's effect on the 5-HT4 receptor where it acts as an agonist.<ref name="Goto-2013">{{cite journal | vauthors = Goto K, Kato G, Kawahara I, Luo Y, Obata K, Misawa H, Ishikawa T, Kuniyasu H, Nabekura J, Takaki M | display-authors = 6 | title = In vivo imaging of enteric neurogenesis in the deep tissue of mouse small intestine | journal = PLOS ONE | volume = 8 | issue = 1 | article-number = e54814 | year = 2013 | pmid = 23382976 | pmc = 3561410 | doi = 10.1371/journal.pone.0054814 | bibcode = 2013PLoSO...854814G | doi-access = free }}</ref>

Its common side effects include dry mouth, abdominal pain, dizziness, headache, insomnia, malaise, nausea, diarrhea and sometimes constipation.<ref name="pmid18457463"/><ref>[http://www.drugsupdate.com/generic/view/328 Mosapride drug information – Drugs Update India]</ref> Unlike some other prokinetic agents, mosapride has little effect on potassium channels, no effect on hERG transfected cells, and no effect on cardiovascular function that could be detected in tests on humans.<ref name="Tack-2012"/><ref name="Kii-1997">{{cite journal | vauthors = Kii Y, Ito T | title = Effects of 5-HT4-receptor agonists, cisapride, mosapride citrate, and zacopride, on cardiac action potentials in guinea pig isolated papillary muscles | journal = Journal of Cardiovascular Pharmacology | volume = 29 | issue = 5 | pages = 670–5 | date = May 1997 | pmid = 9213211 | doi = 10.1097/00005344-199705000-00016 | doi-access = free }}</ref> Due to the pharmacokinetics of mosapride, it would take 1,000–3,000 times the therapeutic dose to elicit cardiovascular effects.<ref name="Kii-2002">{{cite journal | vauthors = Kii Y, Ito T | title = Drug-induced ventricular tachyarrhythmia in isolated rabbit hearts with atrioventricular block | journal = Pharmacology & Toxicology | volume = 90 | issue = 5 | pages = 246–53 | date = May 2002 | pmid = 12076305 | doi = 10.1034/j.1600-0773.2002.900504.x | doi-access = free }}</ref>

== References == {{reflist}}

Category:Motility stimulants Category:Serotonin receptor agonists Category:Benzamides Category:Morpholines Category:Phenol ethers Category:Chloroarenes Category:4-Fluorophenyl compounds Category:Ethoxy compounds Category:Carboxamides