Bethanechol

Clinical data
Trade names	Urecholine, others
Other names	2-[(aminocarbonyl)oxy]- N,N,N-trimethyl- 1-propanaminium Carbamyl-β-methylcholine
AHFS/Drugs.com	Monograph
MedlinePlus	a682849
Routes of administration	By mouth, subcutaneous
ATC code	N07AB02 (WHO)
Legal status
Legal status	EU: Rx-only[1]
Identifiers
IUPAC name 2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
CAS Number	674-38-4 Y
PubChem CID	2370
IUPHAR/BPS	297
DrugBank	DB01019 Y
ChemSpider	2280 Y
UNII	004F72P8F4
KEGG	C06850 Y
ChEBI	CHEBI:3084 Y
ChEMBL	ChEMBL1482 Y
CompTox Dashboard (EPA)	DTXSID5048398
Chemical and physical data
Formula	C7H17N2O2
Molar mass	161.225 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC(C)C[N+](C)(C)C)N
InChI InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1 Y Key:NZUPCNDJBJXXRF-UHFFFAOYSA-O Y
(verify)

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^[2] and is sometimes given orally or subcutaneously to treat urinary retention^[3] 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.^[4]

Atropine is given preoperatively to prevent voiding of the bowel/bladder during surgery; then, bethanechol is given postoperatively to revert this action.^[5]

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

External links

• "Bethanechol". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 28 June 2019.