BETHANECHOL CHLORIDE

First approved in 1948

Details

Stereochemistry	RACEMIC
Molecular Formula	C7H17N2O2.Cl
Molecular Weight	196.675
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
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 168 Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827\|https://adisinsight.springer.com/drugs/800033659	Agonist 2752	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 2752	4.04 null [pKi]
Muscarinic acetylcholine receptor M3 160 Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827\|https://adisinsight.springer.com/drugs/800033659	Agonist 2752	4.15 null [pKi]
Muscarinic acetylcholine receptor M4 87 Target ID: CHEMBL1821 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9224827\|https://adisinsight.springer.com/drugs/800033659	Agonist 2752	4.03 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary retention 2 Sources: https://www.drugs.com/pro/bethanechol.html	Primary		Approved 8583	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 Health Status: unhealthy Age Group: 31-71 Sex: M+F 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 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 Health Status: unhealthy Sex: F 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 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 Health Status: unhealthy Sex: M+F 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
Angiotensin II-induced relaxation of anococcygeus smooth muscle via desensitization of AT1 receptor, and activation of AT2 receptor associated with nitric-oxide synthase pathway.	2004-10	15178697
Fluoxetine and sertraline stimulate gastric acid secretion via a vagal pathway in anaesthetised rats.	2004-09	15225675
Regional gastric contractility alterations in a diabetic gastroparesis mouse model: effects of cholinergic and serotoninergic stimulation.	2004-09	15107299
Reduction of SNAP25 in acid secretion defect of Foxl1-/- gastric parietal cells.	2004-07-30	15240114
Prostaglandin E2 and bethanechol in combination for treating detrusor underactivity.	2004-07	15217463
Antiulcerogenic activity of ethanol extract of Solanum variabile (false "jurubeba").	2004-07	15182909
Acute exposure to methylmercury causes Ca2+ dysregulation and neuronal death in rat cerebellar granule cells through an M3 muscarinic receptor-linked pathway.	2004-07	15141107
Effects of TAK-802, a novel acetylcholinesterase inhibitor, and various cholinomimetics on the urodynamic characteristics in anesthetized guinea pigs.	2004-06-28	15212979
Contractile activity of mouse small intestinal longitudinal smooth muscle.	2004-05-15	15100002
TNF-alpha hyperpolarizes membrane potential and potentiates the response to nicotinic receptor stimulation in cultured rat myenteric neurones.	2004-05	15086448
Over expression of smooth muscle specific caldesmon by transfection and intermittent agonist induced contraction alters cellular morphology and restores differentiated smooth muscle phenotype.	2004-05	15076319
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.	2004-05	15041481
Peripheral PACAP inhibits gastric acid secretion through somatostatin release in mice.	2004-05	15023860
Lower urinary tract dysfunction in Machado-Joseph disease: a study of 11 clinical-urodynamic observations.	2004-03-15	14759635
Fetal gastrointestinal motility in a rabbit model of gastroschisis.	2004-03	15017553
Gastric antiulcer activity of Syngonanthus arthrotrichus SILVEIRA.	2004-03	14993797
Effects of TAK-802, a novel acetylcholinesterase inhibitor, on distension-induced rhythmic bladder contractions in rats and guinea pigs.	2004-02-06	14757154
The efficacy of pilocarpine and bethanechol upon saliva production in cancer patients with hyposalivation following radiation therapy.	2004-02	14970777
Micturition disturbance in acute idiopathic autonomic neuropathy.	2004-02	14742606
Decrease in maximal force generation in the neonatal mouse bladder corresponds to shift in myosin heavy chain isoform composition.	2004-02	14713839
Combination of a cholinergic drug and an alpha-blocker is more effective than monotherapy for the treatment of voiding difficulty in patients with underactive detrusor.	2004-02	14706012
Effects of hypoxia and putative transmitters on [Ca2+]i of rat glomus cells.	2004-01-09	14672819
Prostaglandin E2 and bethanechol in combination for treating detrusor underactivity.	2004-01	14678375
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
In vitro effects of cisapride, metoclopramide and bethanechol on smooth muscle preparations from abomasal antrum and duodenum of dairy cows.	2003-12	14962052
Role of leptin in the control of postprandial pancreatic enzyme secretion.	2003-12	14726613
Short fasting dramatically decreases rat duodenal secretory responsiveness to orexin A but not to VIP or melatonin.	2003-12	12869385
P2X2 subunits contribute to fast synaptic excitation in myenteric neurons of the mouse small intestine.	2003-11-01	12937291
Chronic extrinsic denervation of the small bowel: effect on adrenergic and cholinergic contractile mechanisms in canine ileal circular muscle.	2003-11	14639357
In vivo characterization of 5-HT1A receptor-mediated gastric relaxation in conscious dogs.	2003-11	14517177
Glucose acts in the CNS to regulate gastric motility during hypoglycemia.	2003-11	12869364
Development of ovine fetal ileal motility: role of muscarinic receptor subtypes.	2003-10	14586333
The cholinomimetic agent bethanechol activates IK(ACh) in feline atrial myocytes.	2003-10	12961062
Myoclonus and urinary retention following subarachnoid morphine injection in a dog.	2003-10	12925183
Mechanisms of altered vagal control in heart failure: influence of muscarinic receptors and acetylcholinesterase activity.	2003-10	12829433
Ipratropium bromide for treatment of bethanechol-induced sialorrhea.	2003-09	12921524
Pharmacological characterization of isolated human prostate.	2003-09	12913765
Immunomodulatory effects of inhaled carbon monoxide on rat syngeneic small bowel graft motility.	2003-09	12912858
Peristalsis is impaired in the small intestine of mice lacking the P2X3 subunit.	2003-08-15	12813150
Study of the afferent nervous system and its evaluation in women with impaired detrusor contractility treated with bethanechol.	2003-07	12837422
Muscarinic receptors control glucagon-like peptide 1 secretion by human endocrine L cells.	2003-07	12810581
Selective activation by photodynamic action of cholecystokinin receptor in the freshly isolated rat pancreatic acini.	2003-06	12813011
An embryonic chick pancreas organ culture model: characterization and neural control of exocrine release.	2003-05-30	12798208
Neuronal adrenergic and muscular cholinergic contractile hypersensitivity in canine jejunum after extrinsic denervation.	2003-05-24	12763419
Nitric oxide-dependent in vitro secretion of amylase from innervated or chronically denervated parotid glands of the rat in response to isoprenaline and vasoactive intestinal peptide.	2003-05	12719762
Murine in vitro whole bladder physiology.	2003	15088916
[Cluttering/tachyphemia].	2003	14626073
Uroneurological assessment of spina bifida cystica and occulta.	2003	12808708
Dyssynergic vesicourethral responses during bladder rehabilitation in spinal cord injury patients: effects of suprapubic percussion, credé method and bethanechol chloride.	1976-05	1271553

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

DUVOID

Preferred 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

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