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Identification
NameBethanechol
Accession NumberDB01019  (APRD00051)
TypeSmall Molecule
GroupsApproved
Description

Bethanechol is a synthetic ester structurally and pharmacologically related to acetylcholine. A slowly hydrolyzed muscarinic agonist with no nicotinic effects, bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, cardiac rate changes, and bronchial spasms. [PubChem]

Structure
Thumb
Synonyms
(2-Hydroxypropyl)trimethylammonium carbamate
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
2-Carbamoyloxypropyl-trimethylazanium
Amidopropyldimethylbetaine
Bethanechol
Carbamoyl-beta-methylcholine
carbamoyl-β-methylcholine
Carbamyl-beta-methylcholine
carbamyl-β-methylcholine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Duvoid Tablets 10 mgtablet10 mgoralPaladin Labs Inc1992-12-31Not applicableCanada
Duvoid Tablets 25 mgtablet25 mgoralPaladin Labs Inc1992-12-31Not applicableCanada
Duvoid Tablets 50 mgtablet50 mgoralPaladin Labs Inc1992-12-31Not applicableCanada
Myotonachol Tablets 10mgtablet10 mgoralGlenwood Laboratories Canada Ltd.1993-12-312010-07-16Canada
Myotonachol Tablets 25mgtablet25 mgoralGlenwood Laboratories Canada Ltd.1993-12-312010-07-16Canada
PHL-bethanechol Chloridetablet10 mgoralPharmel Inc1998-02-17Not applicableCanada
PHL-bethanechol Chloridetablet50 mgoralPharmel Inc1998-02-17Not applicableCanada
PHL-bethanechol Chloridetablet25 mgoralPharmel Inc1998-02-17Not applicableCanada
PMS-bethanechol Chloride Tab 10mgtablet10 mgoralPharmascience Inc1990-12-31Not applicableCanada
PMS-bethanechol Chloride Tab 25mgtablet25 mgoralPharmascience Inc1990-12-31Not applicableCanada
PMS-bethanechol Chloride Tab 50mgtablet50 mgoralPharmascience Inc1990-12-31Not applicableCanada
Urecholine Inj 5mg/mlliquid5 mgsubcutaneousMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1976-12-312003-01-31Canada
Urecholine Tab 10mgtablet10 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1976-12-312001-03-21Canada
Urecholine Tab 25mgtablet25 mgoralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1976-12-312001-01-25Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bethanechol Chloridetablet50 mg/1oralPliva Inc.1990-09-30Not applicableUs
Bethanechol Chloridetablet25 mg/1oralUpsher Smith Laboratories, Inc.2010-01-24Not applicableUs
Bethanechol Chloridetablet5 mg/1oralRising Pharmaceuticals Inc.2010-08-24Not applicableUs
Bethanechol Chloridetablet10 mg/1oralWockhardt Limited2003-09-29Not applicableUs
Bethanechol Chloridetablet50 mg/1oralWockhardt Limited2003-09-29Not applicableUs
Bethanechol Chloridetablet5 mg/1oralMajor Pharmaceuticals2010-04-01Not applicableUs
Bethanechol Chloridetablet25 mg/1oralRising Pharmaceuticals Inc.2010-04-06Not applicableUs
Bethanechol Chloridetablet5 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories, Inc.2007-05-01Not applicableUs
Bethanechol Chloridetablet10 mg/1oralAmerican Health Packaging2007-02-20Not applicableUs
Bethanechol Chloridetablet10 mg/1oralLannett Company, Inc.2008-03-27Not applicableUs
Bethanechol Chloridetablet10 mg/1oralGolden State Medical Supply, Inc.2010-04-06Not applicableUs
Bethanechol Chloridetablet25 mg/1oralAv Kare, Inc.2010-04-01Not applicableUs
Bethanechol Chloridetablet25 mg/1oralPliva Inc.1990-09-30Not applicableUs
Bethanechol Chloridetablet10 mg/1oralUpsher Smith Laboratories, Inc.2010-01-24Not applicableUs
Bethanechol Chloridetablet50 mg/1oralWockhardt USA LLC.2003-09-29Not applicableUs
Bethanechol Chloridetablet5 mg/1oralWockhardt Limited2003-09-29Not applicableUs
Bethanechol Chloridetablet50 mg/1oralAmneal Pharmaceuticals of New York, LLC2007-11-21Not applicableUs
Bethanechol Chloridetablet5 mg/1oralLannett Company, Inc.2008-03-27Not applicableUs
Bethanechol Chloridetablet5 mg/1oralGolden State Medical Supply, Inc.2010-08-24Not applicableUs
Bethanechol Chloridetablet50 mg/1oralMarlex Pharmaceuticals Inc2015-04-01Not applicableUs
Bethanechol Chloridetablet5 mg/1oralUpsher Smith Laboratories, Inc.2010-01-24Not applicableUs
Bethanechol Chloridetablet25 mg/1oralWockhardt USA LLC.2003-09-29Not applicableUs
Bethanechol Chloridetablet25 mg/1oralPhysicians Total Care, Inc.1995-08-14Not applicableUs
Bethanechol Chloridetablet10 mg/1oralPliva Inc.1990-09-30Not applicableUs
Bethanechol Chloridetablet50 mg/1oralLannett Company, Inc.2008-03-27Not applicableUs
Bethanechol Chloridetablet25 mg/1oralCaraco Pharmaceutical Laboratories, Ltd.2009-04-30Not applicableUs
Bethanechol Chloridetablet25 mg/1oralMarlex Pharmaceuticals Inc2015-04-01Not applicableUs
Bethanechol Chloridetablet25 mg/1oralAmneal Pharmaceuticals of New York, LLC2007-11-21Not applicableUs
Bethanechol Chloridetablet10 mg/1oralWockhardt USA LLC.2003-09-29Not applicableUs
Bethanechol Chloridetablet25 mg/1oralREMEDYREPACK INC.2013-09-19Not applicableUs
Bethanechol Chloridetablet5 mg/1oralPliva Inc.1990-09-30Not applicableUs
Bethanechol Chloridetablet25 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-11-21Not applicableUs
Bethanechol Chloridetablet50 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories, Inc.2007-05-01Not applicableUs
Bethanechol Chloridetablet5 mg/1oralCaraco Pharmaceutical Laboratories, Ltd.2009-04-30Not applicableUs
Bethanechol Chloridetablet10 mg/1oralMarlex Pharmaceuticals Inc2015-04-01Not applicableUs
Bethanechol Chloridetablet10 mg/1oralAmneal Pharmaceuticals of New York, LLC2007-11-21Not applicableUs
Bethanechol Chloridetablet5 mg/1oralWockhardt USA LLC.2003-09-29Not applicableUs
Bethanechol Chloridetablet25 mg/1oralAv Pak2007-01-11Not applicableUs
Bethanechol Chloridetablet5 mg/1oralAvera Mc Kennan Hospital2015-03-19Not applicableUs
Bethanechol Chloridetablet25 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2003-09-29Not applicableUs
Bethanechol Chloridetablet50 mg/1oralCaraco Pharmaceutical Laboratories, Ltd.2009-04-30Not applicableUs
Bethanechol Chloridetablet25 mg/1oralMajor Pharmaceuticals2010-04-01Not applicableUs
Bethanechol Chloridetablet5 mg/1oralAmneal Pharmaceuticals of New York, LLC2007-11-21Not applicableUs
Bethanechol Chloridetablet25 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories, Inc.2007-05-01Not applicableUs
Bethanechol Chloridetablet50 mg/1oralGolden State Medical Supply, Inc.2010-04-06Not applicableUs
Bethanechol Chloridetablet10 mg/1oralAv Pak2007-01-11Not applicableUs
Bethanechol Chloridetablet25 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Bethanechol Chloridetablet10 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2003-09-29Not applicableUs
Bethanechol Chloridetablet50 mg/1oralUpsher Smith Laboratories, Inc.2010-01-24Not applicableUs
Bethanechol Chloridetablet10 mg/1oralRising Pharmaceuticals Inc.2010-04-06Not applicableUs
Bethanechol Chloridetablet25 mg/1oralWockhardt Limited2003-09-29Not applicableUs
Bethanechol Chloridetablet10 mg/1oralCaraco Pharmaceutical Laboratories, Ltd.2009-04-30Not applicableUs
Bethanechol Chloridetablet10 mg/1oralMajor Pharmaceuticals2010-04-01Not applicableUs
Bethanechol Chloridetablet50 mg/1oralRising Pharmaceuticals Inc.2010-04-06Not applicableUs
Bethanechol Chloridetablet10 mg/1oralGlobal Pharmaceuticals, Division of Impax Laboratories, Inc.2007-05-01Not applicableUs
Bethanechol Chloridetablet25 mg/1oralGolden State Medical Supply, Inc.2010-04-06Not applicableUs
Bethanechol Chloridetablet50 mg/1oralAv Kare, Inc.2010-04-01Not applicableUs
Bethanechol Chloridetablet10 mg/1oralAmerican Health Packaging2015-01-15Not applicableUs
Bethanechol Chloridetablet25 mg/1oralLannett Company, Inc.2008-03-27Not applicableUs
Urecholinetablet25 mg/1oralTeva Women's Health, Inc.2000-04-01Not applicableUs
Urecholinetablet5 mg/1oralTeva Women's Health, Inc.2001-02-01Not applicableUs
Urecholinetablet10 mg/1oralTeva Women's Health, Inc.2001-02-01Not applicableUs
Urecholinetablet50 mg/1oralTeva Women's Health, Inc.2001-02-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DuvoidRoberts
MyotonacholGlenwood
MyotonineNot Available
UrabethNot Available
Uro-CarbHamilton
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Bethanechol Chloride
590-63-6
Thumb
  • InChI Key: XXRMYXBSBOVVBH-UHFFFAOYNA-N
  • Monoisotopic Mass: 196.097855505
  • Average Mass: 196.675
DBSALT000234
Categories
UNII004F72P8F4
CAS number674-38-4
WeightAverage: 161.2221
Monoisotopic: 161.129002798
Chemical FormulaC7H17N2O2
InChI KeyInChIKey=NZUPCNDJBJXXRF-UHFFFAOYSA-O
InChI
InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
IUPAC Name
1-(trimethylazaniumyl)propan-2-yl carbamate
SMILES
CC(C[N+](C)(C)C)OC(N)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholines. These are organic compounds containing a N,N,N-trimethylethanolammonium cation.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassQuaternary ammonium salts
Sub ClassCholines
Direct ParentCholines
Alternative Parents
Substituents
  • Choline
  • Hydrocarbon derivative
  • Organooxygen compound
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.
PharmacodynamicsBethanechol is a parasympathomimetic (cholinergic) used for the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention. Bethanechol, a cholinergic agent, is a synthetic ester which is structurally and pharmacologically related to acetylcholine. It increases the tone of the detrusor urinae muscle, usually producing a contraction sufficiently strong to initiate micturition and empty the bladder. It stimulates gastric motility, increases gastric tone, and often restores impaired rhythmic peristalsis. Bethanechol chloride is not destroyed by cholinesterase and its effects are more prolonged than those of acetytcholine.
Mechanism of actionBethanechol directly stimulates cholinergic receptors in the parasympathetic nervous system while stimulating the ganglia to a lesser extent. Its effects are predominantly muscarinic, inducing little effect on nicotinic receptors and negligible effects on the cardiovascular system.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8407
Blood Brain Barrier+0.9789
Caco-2 permeable+0.5251
P-glycoprotein substrateNon-substrate0.7295
P-glycoprotein inhibitor INon-inhibitor0.9508
P-glycoprotein inhibitor IINon-inhibitor0.8371
Renal organic cation transporterNon-inhibitor0.9209
CYP450 2C9 substrateNon-substrate0.8304
CYP450 2D6 substrateNon-substrate0.8066
CYP450 3A4 substrateSubstrate0.5216
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9522
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9047
Ames testNon AMES toxic0.6804
CarcinogenicityCarcinogens 0.522
BiodegradationNot ready biodegradable0.8058
Rat acute toxicity2.7833 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9852
hERG inhibition (predictor II)Non-inhibitor0.8915
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sun pharmaceutical industries inc
  • Odyssey pharmaceuticals inc
  • Able laboratories inc
  • Actavis totowa llc
  • Amneal pharmaceutical
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Emcure pharmaceuticals usa inc
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lannett holdings inc
  • Lannett co inc
  • Pharmax group inc
  • Sandoz inc
  • Upsher smith laboratories inc
  • Watson laboratories inc
  • Wockhardt ltd
  • Wellspring pharmaceutical corp
  • Glenwood inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral10 mg/1
Tabletoral25 mg/1
Tabletoral5 mg/1
Tabletoral50 mg/1
Tabletoral10 mg
Tabletoral25 mg
Tabletoral50 mg
Liquidsubcutaneous5 mg
Prices
Unit descriptionCostUnit
Bethanechol chloride powder10.1USD g
Urecholine 50 mg tablet3.95USD tablet
Urecholine 25 mg tablet3.46USD tablet
Bethanechol Chloride 50 mg tablet2.97USD tablet
Bethanechol 50 mg tablet2.85USD tablet
Bethanechol Chloride 25 mg tablet1.86USD tablet
Urecholine 10 mg tablet1.85USD tablet
Bethanechol 25 mg tablet1.78USD tablet
Bethanechol Chloride 10 mg tablet1.39USD tablet
Bethanechol 10 mg tablet1.34USD tablet
Urecholine 5 mg tablet1.14USD tablet
Bethanechol Chloride 5 mg tablet0.74USD tablet
Bethanechol 5 mg tablet0.71USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting pointabout 220Major, R.T. and Bonnett, H.T.; U.S. Patent 2,322,375: June 22,1943; assigned to Merck & Co., Inc.
water solubility10 mg/mL (chloride salt)Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.311 mg/mLALOGPS
logP-2.8ALOGPS
logP-4.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)15.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.44 m3·mol-1ChemAxon
Polarizability17.73 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Major, R.T. and Bonnett, H.T.; U.S. Patent 2,322,375: June 22,1943; assigned to Merck &
Co., Inc.

General ReferencesNot Available
External Links
ATC CodesN07AB02
AHFS Codes
  • 12:04.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (74.1 KB)
Interactions
Drug Interactions
Drug
CimetropiumBethanechol may decrease the anticholinergic activities of Cimetropium Bromide.
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Bethanechol.
TacrineThe risk or severity of adverse effects can be increased when Tacrine is combined with Bethanechol.
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals to avoid nausea.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then trigge...
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Agrawal A, Hila A, Tutuian R, Mainie I, Castell DO: Bethanechol improves smooth muscle function in patients with severe ineffective esophageal motility. J Clin Gastroenterol. 2007 Apr;41(4):366-70. [PubMed:17413603 ]
  4. Buranakarl C, Kijtawornrat A, Angkanaporn K, Komolvanich S, Bovee KC: Effects of bethanechol on canine urinary bladder smooth muscle function. Res Vet Sci. 2001 Dec;71(3):175-81. [PubMed:11798291 ]
  5. Cruzblanca H: An M2-like muscarinic receptor enhances a delayed rectifier K+ current in rat sympathetic neurones. Br J Pharmacol. 2006 Oct;149(4):441-9. Epub 2006 Sep 4. [PubMed:16953191 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23