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 category	US: C (Risk not ruled out)
Routes of administration	Oral, subcutaneous
Identifiers
CAS Number	674-38-4
ATC code	N07AB02 (WHO)
PubChem	CID 2370
IUPHAR/BPS	297
DrugBank	DB01019
ChemSpider	2280
UNII	004F72P8F4
KEGG	C06850
ChEBI	CHEBI:3084
ChEMBL	CHEMBL1482
Synonyms	2-[(aminocarbonyl)oxy]- N,N,N-trimethyl- 1-propanaminium
Chemical data
Formula	C7H17N2O2
Molar mass	161.221 g/mol
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 Key:NZUPCNDJBJXXRF-UHFFFAOYSA-O
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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).

Uses

Bethanechol alleviates dry mouth^[1] and is sometimes given orally or subcutaneously to treat urinary retention 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.^[2] Bethanechol is a powerful cholinergic agent which does not cross 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.^[3]

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.

See also

• Pilocarpine & Cevimeline - similar parasympathomimetic medicines for dry mouth (Xerostomia)

References

1. Gorsky, Meir; Epstein, Joel B.; Parry, Jamie; Epstein, Matthew S.; Le, Nhu D.; Silverman, Sol (2004-02-01). "The efficacy of pilocarpine and bethanechol upon saliva production in cancer patients with hyposalivation following radiation therapy". Oral Surgery, Oral Medicine, Oral Pathology, Oral Radiology, and Endodontics 97 (2): 190–195. doi:10.1016/S107921040300564X. ISSN 1079-2104. PMID 14970777.
2. Carter WJ (September 2008). "Unexpected benefits of bethanechol in adults with cerebral palsy". Med. J. Aust. 189 (5): 293. PMID 18759732.
3. Obied, Hassan (2011). Cholinergic Pharmacology. CSU.

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