BETHANECHOL CHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C7H17N2O2.Cl
Molecular Weight	196.675
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].CC(C[N+](C)(C)C)OC(N)=O

InChI

InChIKey=XXRMYXBSBOVVBH-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29279881 | https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5513ddc8-90c8-4548-8188-5a807465cdc4

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 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827\|https://adisinsight.springer.com/drugs/800033659	Agonist 2678	4.01 null [pKi]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827\|https://adisinsight.springer.com/drugs/800033659	Agonist 2678	4.04 null [pKi]
Muscarinic acetylcholine receptor M3 159 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827\|https://adisinsight.springer.com/drugs/800033659	Agonist 2678	4.15 null [pKi]
Muscarinic acetylcholine receptor M4 86 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827\|https://adisinsight.springer.com/drugs/800033659	Agonist 2678	4.03 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary retention 2 Sources: https://www.drugs.com/pro/bethanechol.html	Primary		Approved 8429	Bethanechol chloride Approved Use Bethanechol chloride is indicated for the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention. Launch Date 1948

Doses

Dose	Population	Adverse events
50 mg single, intramuscular MTD Dose: 50 mg Route: intramuscular Route: single Dose: 50 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6124217	unhealthy, 31-71 n = 9 Health Status: unhealthy Condition: duodenal ulcer (patients after proximal gastric vagotomy) Age Group: 31-71 Sex: M+F Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/6124217	Sources: https://pubmed.ncbi.nlm.nih.gov/6124217
50 mg 4 times / day multiple, oral Overdose Dose: 50 mg, 4 times / day Route: oral Route: multiple Dose: 50 mg, 4 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5513ddc8-90c8-4548-8188-5a807465cdc4&type=display	unhealthy Health Status: unhealthy Condition: urinary retention Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5513ddc8-90c8-4548-8188-5a807465cdc4&type=display	Other AEs: Abdominal discomfort, Salivation... Other AEs: Abdominal discomfort Salivation Flushed skin Sweating Nausea Vomiting Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=5513ddc8-90c8-4548-8188-5a807465cdc4&type=display
20 mg 3 times / day multiple, oral Recommended Dose: 20 mg, 3 times / day Route: oral Route: multiple Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21546875	unhealthy n = 31 Health Status: unhealthy Condition: bladder dysfunction after type III radical hysterectomy Sex: F Population Size: 31 Sources: https://pubmed.ncbi.nlm.nih.gov/21546875	Other AEs: Nausea, Abdominal distension... Other AEs: Nausea (12.9%) Abdominal distension (6.4%) Abdominal cramps (9.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/21546875
50 mg 3 times / day multiple, oral (max) Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16927740	unhealthy n = 18 Health Status: unhealthy Condition: xerostomia Sex: M+F Population Size: 18 Sources: https://pubmed.ncbi.nlm.nih.gov/16927740	Other AEs: Sweating, Flushing... Other AEs: Sweating (27%) Flushing (27%) Stomach cramps (12%) Diarrhea (12%) Headache (17%) Dizziness (17%) Visual disorders NEC (12%) Urination abnormal NOS (28%) Sources: https://pubmed.ncbi.nlm.nih.gov/16927740

AEs

Sourcing

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

PubMed

Title	Date	PubMed
Aging effects on contractility of longitudinal and circular detrusor and trigone of rat bladder.	2001 Aug	11458124
PYY inhibits CCK-stimulated pancreatic secretion through the area postrema in unanesthetized rats.	2001 Aug	11448870
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
Differences in Ca(2+) signaling underlie age-specific effects of secretagogues on colonic Cl(-) transport.	2001 Mar	11171585
Inhibition of gastric acid secretion by saiboku-to, an oriental herbal medicine, in rats.	2001 May	11341671
Cholinergic stimulation enhances colonic motor activity, transit, and sensation in humans.	2001 Nov	11668032
Dependency of detrusor contractions on calcium sensitization and calcium entry through LOE-908-sensitive channels.	2001 Sep	11522599
Secretion of the trefoil factor TFF3 from the isolated vascularly perfused rat colon.	2001 Sep 15	11495677
Impaired gastrocolonic response and peristaltic reflex in slow-transit constipation: role of 5-HT(3) pathways.	2002 Aug	12121888
Different role of the histamine H3-receptor in vagal-, betanechol-, pentagastrin-induced gastric acid secretion in anaesthetized rats.	2002 Jul	12190086
Generation of a cell line with smooth muscle phenotype from hypertrophied urinary bladder.	2002 Jul	12055106
Muscarinic receptors control postprandial release of glucagon-like peptide-1: in vivo and in vitro studies in rats.	2002 Jun	12021207
Pharmacologic treatment of anal fissure with botoxin, diltiazem, or bethanechol.	2002 May-Jun	12022973
Antagonistic effects of CompB on orphanin FQ-induced colonic contractions in rats.	2002 Nov 1	12409005
Antisecretory effect of somatostatin on gastric acid via inhibition of histamine release in isolated mouse stomach.	2002 Oct 4	12354575
[Cluttering/tachyphemia].	2003	14626073
Pharmacological discrimination between muscarinic receptor signal transduction cascades with bethanechol chloride.	2003 Apr	12711626
Role of leptin in the control of postprandial pancreatic enzyme secretion.	2003 Dec	14726613
Muscarinic receptors couple to modulation of nicotinic ACh receptor desensitization in myenteric neurons.	2003 Jul	12620888
Selective activation by photodynamic action of cholecystokinin receptor in the freshly isolated rat pancreatic acini.	2003 Jun	12813011
ERG K+ channels modulate the electrical and contractile activities of gallbladder smooth muscle.	2003 Mar	12431906
An embryonic chick pancreas organ culture model: characterization and neural control of exocrine release.	2003 May 30	12798208
P2X2 subunits contribute to fast synaptic excitation in myenteric neurons of the mouse small intestine.	2003 Nov 1	12937291
Pharmacological characterization of isolated human prostate.	2003 Sep	12913765
Acetylcholine release in the pontine reticular formation of C57BL/6J mouse is modulated by non-M1 muscarinic receptors.	2004	15207318
Successful pharmacotherapy for an adult case with prolonged symptoms of postganglionic cholinergic dysautonomia.	2004	15159611
Prostaglandin E2 and bethanechol in combination for treating detrusor underactivity.	2004 Jul	15217463
Acute exposure to methylmercury causes Ca2+ dysregulation and neuronal death in rat cerebellar granule cells through an M3 muscarinic receptor-linked pathway.	2004 Jul	15141107
Fetal gastrointestinal motility in a rabbit model of gastroschisis.	2004 Mar	15017553
Lower urinary tract dysfunction in Machado-Joseph disease: a study of 11 clinical-urodynamic observations.	2004 Mar 15	14759635
Expressions of CCAAT-enhancer-binding proteins and c-Myc in the parotid gland of the rat: in vivo effects of isoprenaline, bethanechol, vasoactive intestinal peptide and food intake.	2004 May	15041481

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

Name

Type

Language

BETHANECHOL CHLORIDE

Common Name

English

Bethanechol chloride [WHO-DD]

Common Name

English

BETHANECHOL CHLORIDE [USP-RS]

Common Name

English

MYOTONACHOL

Brand Name

English

BETHANECHOL CHLORIDE [JAN]

Common Name

English

URECHOLINE

Brand Name

English

1-PROPANAMINIUM, 2-((AMINOCARBONYL)OXY)-N,N,N-TRIMETHYL-, CHLORIDE, (±)-

Systematic Name

English

NSC-30783

Code

English

BETHANECHOL CHLORIDE [USP MONOGRAPH]

Common Name

English

DUVOID

Brand Name

English

BETHANECHOL CHLORIDE [MI]

Common Name

English

BETHANECHOL CHLORIDE [ORANGE BOOK]

Common Name

English

BETHANECHOL CHLORIDE [MART.]

Common Name

English

(±)-(2-HYDROXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE CARBAMATE

Systematic Name

English

BETHANECHOL CHLORIDE [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704