Bethanechol

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Bethanechol
Systematic (IUPAC) name
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
Clinical data
Trade namesUrecholine
AHFS/Drugs.commonograph
MedlinePlusa682849
Pregnancy cat.C (US)
Legal status ?
RoutesOral, subcutaneous
Identifiers
CAS number674-38-4 YesY
ATC codeN07AB02
PubChemCID 2370
IUPHAR ligand297
DrugBankDB01019
ChemSpider2280 YesY
UNII004F72P8F4 YesY
KEGGC06850 YesY
ChEBICHEBI:3084 YesY
ChEMBLCHEMBL1482 YesY
Synonyms2-[(aminocarbonyl)oxy]- N,N,N-trimethyl- 1-propanaminium
Chemical data
FormulaC7H17N2O2 
Mol. mass161.221 g/mol
 YesY (what is this?)  (verify)
 
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Bethanechol
Systematic (IUPAC) name
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
Clinical data
Trade namesUrecholine
AHFS/Drugs.commonograph
MedlinePlusa682849
Pregnancy cat.C (US)
Legal status ?
RoutesOral, subcutaneous
Identifiers
CAS number674-38-4 YesY
ATC codeN07AB02
PubChemCID 2370
IUPHAR ligand297
DrugBankDB01019
ChemSpider2280 YesY
UNII004F72P8F4 YesY
KEGGC06850 YesY
ChEBICHEBI:3084 YesY
ChEMBLCHEMBL1482 YesY
Synonyms2-[(aminocarbonyl)oxy]- N,N,N-trimethyl- 1-propanaminium
Chemical data
FormulaC7H17N2O2 
Mol. mass161.221 g/mol
 YesY (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 is sold under the brand names Duvoid (Roberts), Myotonachol (Glenwood), Urecholine (Merck Frosst) and Urocarb (Hamilton).

Uses[edit]

Bethanechol 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 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.[1] 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.[2]

Contraindications[edit]

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[edit]

  1. ^ Carter WJ (September 2008). "Unexpected benefits of bethanechol in adults with cerebral palsy". Med. J. Aust. 189 (5): 293. PMID 18759732. 
  2. ^ 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