Bethanechol

Bethanechol

Systematic (IUPAC) name
2-(carbamoyloxy)- N,N,N-trimethylpropan- 1-aminium
Clinical data
Trade names	Urecholine
AHFS/Drugs.com	monograph
MedlinePlus	a682849
Pregnancy cat.	C (US)
Legal status	?
Routes	Oral, subcutaneous
Identifiers
CAS number	674-38-4 Y
ATC code	N07AB02
PubChem	CID 2370
IUPHAR ligand	297
DrugBank	APRD00051
ChemSpider	2280 Y
UNII	004F72P8F4 Y
KEGG	C06850 Y
ChEBI	CHEBI:3084 Y
ChEMBL	CHEMBL1482 Y
Synonyms	2-[(aminocarbonyl)oxy]- N,N,N-trimethyl- 1-propanaminium
Chemical data
Formula	C7H17N2O2
Mol. mass	161.221 g/mol
SMILES	eMolecules & PubChem
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
N (what is this?)  (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 does not involve the action of the muscarinic M3 receptor subtype in-vitro (Benavides-Haro et al. (2003))

Bethanechol is sold under the brand names Duvoid (Roberts), Myotonachol (Glenwood), Urecholine (Merck Frosst) and Urocarb (Hamilton).

Uses

Bethanechol is sometimes given orally or subcutaneously to treat urinary retention resulting from general anesthetic or diabetic neuropathy of the bladder, or to treat gastrointestinal atony (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. Bethanechol is a powerful cholinergic agent which efficiently crosses the blood - brain barrier and may have powerful nootropic properties in enhancement of neural signaling and processing speed as well.

Atropine is given preoperatively to prevent voiding of the bowel/bladder during surgery, Bethanechol is then given postoperatively to revert this action.

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

(Benavides-Haro et al. (2003)). The cholinomimetic agent bethanechol activates IK(ACh) in feline atrial myocytes. Naunyn-Schmiedederg's Arch Pharmacol. 368:309-315