{{short description|Chemical compound}} {{Use dmy dates|date=September 2017}} {{Drugbox | Watchedfields = changed | verifiedrevid = 457629847 | image = Bethanechol-2D.svg | image_class = skin-invert-image | alt =
<!--Clinical data--> | tradename = Urecholine, others | Drugs.com = {{drugs.com|monograph|bethanechol}} | MedlinePlus = a682849 | pregnancy_category = | routes_of_administration = By mouth, subcutaneous | ATC_prefix = N07 | ATC_suffix = AB02 | ATC_supplemental =
<!-- Legal status --> | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> | legal_AU_comment = | legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> | legal_BR_comment = | legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> | legal_CA_comment = | legal_DE = <!-- Anlage I, II, III or Unscheduled --> | legal_DE_comment = | legal_NZ = <!-- Class A, B, C --> | legal_NZ_comment = | legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C --> | legal_UK_comment = | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | legal_US_comment = | legal_EU = Rx-only | legal_EU_comment = <ref>{{cite web | title = Active substance: bethanechol | work = List of nationally authorised medicinal products, Human Medicines Evaluation Division | publisher = European Medicines Agency | date = 11 February 2021 | url = https://www.ema.europa.eu/documents/psusa/bethanechol-list-nationally-authorised-medicinal-products-psusa/00000402/202006_en.pdf }}</ref> | legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> | legal_UN_comment = | legal_status = <!-- For countries not listed above -->
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 674-38-4 | PubChem = 2370 | IUPHAR_ligand = 297 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB01019 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 2280 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 004F72P8F4 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C06850 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 3084 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1482
<!--Chemical data--> | IUPAC_name = 2-(Carbamoyloxy)-''N'',''N'',''N''-trimethylpropan-1-aminium | C=7 | H=17 | N=2 | O=2 | smiles = O=C(OC(C)C[N+](C)(C)C)N | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = NZUPCNDJBJXXRF-UHFFFAOYSA-O | synonyms = 2-[(aminocarbonyl)oxy]- ''N'',''N'',''N''-trimethyl- 1-propanaminium<br />Carbamyl-β-methylcholine }}
'''Bethanechol''' is a parasympathomimetic choline carbamate that selectively stimulates muscarinic receptors without any effect on nicotinic receptors. Unlike acetylcholine, bethanechol is not hydrolyzed by cholinesterase and will therefore have a long duration of action. Bethanechol is sold under the brand names Duvoid (Roberts), Myotonachol (Glenwood), Urecholine (Merck Frosst), and Urocarb (Hamilton). The name ''bethanechol'' refers to its structure as the urethane of beta-methylcholine.
== Medical uses ==
Bethanechol alleviates dry mouth<ref>{{cite journal | vauthors = Gorsky M, Epstein JB, Parry J, Epstein MS, Le ND, Silverman S | title = The efficacy of pilocarpine and bethanechol upon saliva production in cancer patients with hyposalivation following radiation therapy | journal = Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, and Endodontics | volume = 97 | issue = 2 | pages = 190–195 | date = February 2004 | pmid = 14970777 | doi = 10.1016/j.tripleo.2003.08.031 }}</ref> and is sometimes given orally or subcutaneously to treat urinary retention<ref>{{cite journal | vauthors = Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM | title = The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis | journal = Neurourology and Urodynamics | volume = 41 | issue = 1 | pages = 127–139 | date = January 2022 | pmid = 34816481 | doi = 10.1002/nau.24839 | s2cid = 244530010 | url = https://pure.bond.edu.au/ws/files/118955227/AM_The_effectiveness_of_parasympathomimetics_for_treating.pdf }}</ref> resulting from general anesthetic, diabetic neuropathy of the bladder, or a side effect of antidepressants; or to treat gastrointestinal lack of muscular tone. The muscarinic receptors in the bladder and gastrointestinal tract stimulate contraction of the bladder and expulsion of urine, and increased gastrointestinal motility, respectively. Bethanechol should be used to treat these disorders only after mechanical obstruction is ruled out as a possible cause.
Its potential benefit in the treatment of cerebral palsy has been investigated.<ref name="pmid18759732">{{cite journal | vauthors = Carter WJ | title = Unexpected benefits of bethanechol in adults with cerebral palsy | journal = The Medical Journal of Australia | volume = 189 | issue = 5 | pages = 293 | date = September 2008 | pmid = 18759732 | doi = 10.5694/j.1326-5377.2008.tb02034.x | s2cid = 29048832 }}</ref>
Atropine is given preoperatively to prevent voiding of the bowel/bladder during surgery; then, bethanechol is given postoperatively to revert this action.<ref>{{cite book|last=Obied|first=Hassan | name-list-style = vanc |title=Cholinergic Pharmacology|year=2011|publisher=CSU}}</ref>
== Contraindications ==
Use of bethanechol, as well as all other muscarinic receptor agonists, is contraindicated in patients with asthma, coronary insufficiency, peptic ulcers, intestinal obstruction and hyperthyroidism. The parasympathomimetic action of this drug will exacerbate the symptoms of these disorders.
== References == {{Reflist}}
== External links == * {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/bethanechol | archive-url = https://web.archive.org/web/20190628211729/https://druginfo.nlm.nih.gov/drugportal/name/bethanechol | url-status = dead | archive-date = 28 June 2019 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Bethanechol }}
{{Urologicals}} {{Muscarinic acetylcholine receptor modulators}} {{Portal bar | Medicine}}
Category:Carbamates Category:Choline esters Category:M1 receptor agonists Category:M2 receptor agonists Category:M3 receptor agonists Category:M4 receptor agonists Category:M5 receptor agonists Category:Peripherally selective drugs Category:Quaternary ammonium compounds