BETHANECHOL

Details

Stereochemistry	RACEMIC
Molecular Formula	C7H17N2O2
Molecular Weight	161.2221
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

SMILES

CC(C[N+](C)(C)C)OC(N)=O

InChI

InChIKey=NZUPCNDJBJXXRF-UHFFFAOYSA-O

InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1

HIDE SMILES / InChI

Molecular Formula	C7H17N2O2
Molecular Weight	161.2221
Charge	1
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

Bethanechol is a parasympathomimetic choline carbamate that selectively stimulates muscarinic receptors with little effect on nicotinic receptors. Bethanechol is indicated for the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M1 169	Agonist 2,678	4.01 null [pKi]
Muscarinic acetylcholine receptor M2 121	Agonist 2,678	4.04 null [pKi]
Muscarinic acetylcholine receptor M3 159	Agonist 2,678	4.15 null [pKi]
Muscarinic acetylcholine receptor M4 86	Agonist 2,678	4.03 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary retention 2	Primary		Approved 8,429	Bethanechol chloride

Doses

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Dose	Population	Adverse events
50 mg single, intramuscular MTD	unhealthy, 31-71
50 mg 4 times / day multiple, oral Overdose	unhealthy	Other AEs: Abdominal discomfort, Salivation...
20 mg 3 times / day multiple, oral Recommended	unhealthy	Other AEs: Nausea, Abdominal distension...
50 mg 3 times / day multiple, oral Recommended	unhealthy	Other AEs: Sweating, Flushing...

Showing 1 to 4 of 4 entries

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AEs

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AE	Dose	Population
Abdominal discomfort	50 mg 4 times / day multiple, oral Overdose	unhealthy
Flushed skin	50 mg 4 times / day multiple, oral Overdose	unhealthy
Nausea	50 mg 4 times / day multiple, oral Overdose	unhealthy
Salivation	50 mg 4 times / day multiple, oral Overdose	unhealthy
Sweating	50 mg 4 times / day multiple, oral Overdose	unhealthy

Showing 1 to 5 of 17 entries

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3084	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3084
MolPort	MolPort-006-167-685	https://www.molport.com/shop/molecule-link/MolPort-006-167-685

Showing 1 to 2 of 2 entries

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PubMed

Show entries

Title	Date	PubMed
Cholinergic stimulation of the lower esophageal sphincter in patients with vagotomy and antrectomy.	1975 Mar	1124744
Selective involvement of calcium and calcium channels in stimulated mucin secretion from rat colon.	2001 Dec	11761027
Regional differences in the response of feline esophageal smooth muscle to stretch and cholinergic stimulation.	2001 Dec	11705751
Effects of YM905, a novel muscarinic M3-receptor antagonist, on experimental models of bowel dysfunction in vivo.	2001 Jul	11488427
Stimulatory effects of nitric oxide donors on gastric acid secretion in isolated mouse stomach.	2001 May 25	11408038

Showing 1 to 5 of 24 entries

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Patents

Sample Use Guides

In Vivo Use Guide

The usual adult oral dose ranges from 10 to 50 mg three or four times a day. The minimum effective dose is determined by giving 5 to 10 mg initially and repeating the same amount at hourly intervals until satisfactory response occurs, or until a maximum of 50 mg has been given. The effects of the drug sometimes appear within 30 minutes and are usually maximal within 60 to 90 minutes. The drug effects persist for about one hour.

Route of Administration: Oral