otilonium bromide
{{Short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 408354493
| IUPAC_name = N,N-Diethyl-N-methyl-2-(4-[2-(octyloxy)benzamido]benzoyloxy)ethanaminium bromide
| image = Otilonium bromide.png
| tradename = Spasmoctyl 40, Doralin, Menoctyl
| Drugs.com = {{drugs.com|international|otilonium-bromide}}
| pregnancy_AU =
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| legal_AU =
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| routes_of_administration =
| bioavailability =
| protein_bound =
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| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 26095-59-0
| ATC_prefix = A03
| ATC_suffix = AB06
| PubChem = 72092
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 21HN3N72PV
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07083
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 65077
| C = 29
| H = 43
| Br = 1
| N = 2
| O = 4
| smiles = CCCCCCCCOC1=CC=CC=C1C(=O)NC2=CC=C(C=C2)C(=O)OCC[N+](C)(CC)CC.[Br-]
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C29H42N2O4.BrH/c1-5-8-9-10-11-14-22-34-27-16-13-12-15-26(27)28(32)30-25-19-17-24(18-20-25)29(33)35-23-21-31(4,6-2)7-3;/h12-13,15-20H,5-11,14,21-23H2,1-4H3;1H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = VWZPIJGXYWHBOW-UHFFFAOYSA-N
}}
Otilonium bromide is a drug used to treat abdominal pain caused by irritable bowel syndrome. It is an antispasmodic, which is useful to treat the symptoms of irritable bowel syndrome by reducing abdominal spasms (colic), bloating, pain, and gut motility.
It is an antimuscarinic and calcium channel blocker used to relieve spasmodic pain of the gut, especially in irritable bowel syndrome.{{cite web|archive-url=https://web.archive.org/web/20160304071357/http://www.grupounipharm.com/sites/default/files/DISMOX+Inserto+CORREGIDO+2011.+Ingl%C3%A9s.pdf|url=http://www.grupounipharm.com/sites/default/files/DISMOX+Inserto+CORREGIDO+2011.+Ingl%C3%A9s.pdf|title=Dismox|archive-date=4 March 2016}} This means it works in the gut themselves, by relaxing the small muscles of the intestines, which results in relieving cramps and therefore reduces pain.
Medical uses
A pooled analysis of three clinical trials suggest that otilonium bromide is more effective than placebo for the treatment of irritable bowel syndrome.{{cite journal | vauthors = Clavé P, Tack J | title = Efficacy of otilonium bromide in irritable bowel syndrome: a pooled analysis | journal = Therapeutic Advances in Gastroenterology | volume = 10 | issue = 3 | pages = 311–322 | date = March 2017 | pmid = 28246548 | pmc = 5305018 | doi = 10.1177/1756283X16681708 }}
Pharmacology
Otilonium bromide binds to both muscarinic receptors and tachykinin NK2 receptors.{{cite journal | vauthors = Evangelista S | title = Otilonium bromide: a selective spasmolytic for the gastrointestinal tract | journal = The Journal of International Medical Research | volume = 27 | issue = 5 | pages = 207–22 | date = 1999 | pmid = 10689627 | doi = 10.1177/030006059902700501 | doi-access = free }} It has been shown to inhibit L-type and T-type calcium channels, actions which may contribute to or determine its effects in the gut.{{cite journal | vauthors = Martin MT, Hove-Madsen L, Jimenez M | title = Otilonium bromide inhibits muscle contractions via L-type calcium channels in the rat colon | journal = Neurogastroenterology and Motility | volume = 16 | issue = 2 | pages = 175–83 | date = April 2004 | pmid = 15086871 | doi = 10.1111/j.1365-2982.2004.00518.x | s2cid = 7315438 }}{{cite journal | vauthors = Strege PR, Sha L, Beyder A, Bernard CE, Perez-Reyes E, Evangelista S, Gibbons SJ, Szurszewski JH, Farrugia G | display-authors = 6 | title = T-type Ca(2+) channel modulation by otilonium bromide | journal = American Journal of Physiology. Gastrointestinal and Liver Physiology | volume = 298 | issue = 5 | pages = G706-13 | date = May 2010 | pmid = 20203058 | pmc = 2867415 | doi = 10.1152/ajpgi.00437.2009 }}
When taken orally, very little of the drug is absorbed into the rest of the body,{{cite journal | vauthors = Shin BS, Kim JJ, Kim J, Hu SK, Kim HJ, Hong SH, Kim HK, Lee HS, Yoo SD | display-authors = 6 | title = Oral bioavailability and enterohepatic recirculation of otilonium bromide in rats | journal = Archives of Pharmacal Research | volume = 31 | issue = 1 | pages = 117–24 | date = January 2008 | pmid = 18277617 | doi = 10.1007/s12272-008-1129-2 | s2cid = 25727036 }} which means that most of its actions remain confined to the gastrointestinal system.
Adverse effects
Otilonium bromide is generally well tolerated and does not have the side-effects observed with similar classes of drugs. {{cite journal | vauthors = Evangelista S | title = Quaternary ammonium derivatives as spasmolytics for irritable bowel syndrome | journal = Current Pharmaceutical Design | volume = 10 | issue = 28 | pages = 3561–3568 | date = November 2004 | pmid = 15579053 | doi = 10.2174/1381612043382972 }} A case of cardiovascular toxicity was reported due to an overdose. {{cite journal | vauthors = Zaki SA, Helal ME, Rashid A | title = Cardiovascular Toxicity Due to Otilonium Bromide Overdose: A Case Report | language = English | journal = The Journal of Emergency Medicine | volume = 62 | issue = 3 | pages = e47-e50 | date = March 2022 | pmid = 35031171 | doi = 10.1016/j.jemermed.2021.10.025 }}{{cite web | url = https://www.medsafe.govt.nz/profs/class/Agendas/agen53OtiloniumBromide.pdf | title = Submission for the classification of Otilonium bromide 40 mg film-coated tables (10 and 30 tablet pack) as Pharmacist Only | work = Arai BioFarma Limited }}
References
{{Reflist}}
{{Drugs for functional gastrointestinal disorders}}
{{Muscarinic acetylcholine receptor modulators}}
Category:Muscarinic antagonists
Category:Quaternary ammonium compounds