Bethanechol

Identification

Summary

Bethanechol is a muscarinic agonist used to treat postoperative and postpartum nonobstructive functional urinary retention and neurogenic atony of the bladder with retention.

Brand Names
Duvoid
Generic Name
Bethanechol
DrugBank Accession Number
DB01019
Background

Bethanechol is a synthetic ester that was initially synthesized in 1935.1,4 As a cholinergic agent, bethanechol is similar in structure and pharmacological function to acetylcholine and is used in specific cases when stimulation of the parasympathetic nervous system is necessary.1,4 For example, bethanechol is readily used to treat postoperative or postpartum urinary retention. An advantage of bethanechol is that in contrast to acetylcholine, bethanechol is not degraded by cholinesterase allowing its effects to be longer-lasting.4

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 161.2221
Monoisotopic: 161.129002798
Chemical Formula
C7H17N2O2
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

Pharmacology

Indication

Bethanechol is indicated for the treatment of acute, functional postpartum and postoperative urinary retention. It is also indicated for the treatment of neurogenic atony of the bladder with retention.3,4

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Bethanechol is selective for muscarinic receptors and has little to no impact on nicotinic receptors.1 The charged quaternary amine in the structure of bethanechol prevents it from crossing the blood-brain barrier which minimizes central nervous system related adverse effects.1

Mechanism of action

Bethanechol is a direct muscarinic agonist and stimulates the parasympathetic nervous system by binding to postganglionic muscarinic receptors.2,1

Though there are 5 types of muscarinic receptors (M1, M2, M3, M4, M5), binding of bethanechol to M3 is most clinically significant since M3 receptors are present in intestinal smooth muscle and the bladder.2 The cholinergic effects of bethanechol lead to increased detrusor muscle tone to promote bladder emptying and increased smooth muscle tone which restores gastrointestinal peristalsis and motility.2

As a result of selectivity for muscarinic receptors, bethanechol produces minimal to no nicotinic effects.1

TargetActionsOrganism
AMuscarinic acetylcholine receptor M3
agonist
Humans
UMuscarinic acetylcholine receptor M1
agonist
Humans
UMuscarinic acetylcholine receptor M2
agonist
Humans
UMuscarinic acetylcholine receptor M4
agonist
Humans
UMuscarinic acetylcholine receptor M5
agonist
Humans
Absorption

After oral administration of bethanechol, maximum effectiveness of the drug on the bladder and GI tract typically occur after 60-90 minutes; however, effects may present as early as 30 minutes after administration. The duration of action of a typical oral dose of bethanechol is around 1 hour while higher doses (300-400 mg) may be effective for up to 6 hours.4

Subcutaneously administered bethanechol produces effects more rapidly after 5-15 minutes with maximum effectiveness achieved after 15-30 minutes. The effects of subcutaneous bethanechol subside within 2 hours of administration.4

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Symptoms of bethanechol overdose include nausea, vomiting, abdominal discomfort, salivation, sweating, and flushing of the skin.4

In case of overdose, atropine sulfate is available as an antidote and although subcutaneous administration is preferred, it may be given intravenously in emergencies. In adults, the recommended dose of atropine is 0.6 mg and may be repeated every 2 hours based on the patient’s response. In infants and children up to 12 years of age, the recommended dose of atropine is 0.01 mg/kg (maximum single dose = 0.04 mg) and may be repeated every 2 hours until the desired response is achieved or until adverse effects of atropine limit usage.4

In mice, the oral LD50 of bethanechol is 1510 mg/kg.4

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Bethanechol.
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Bethanechol.
AmikacinThe therapeutic efficacy of Bethanechol can be decreased when used in combination with Amikacin.
AprotininThe risk or severity of adverse effects can be increased when Aprotinin is combined with Bethanechol.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Bethanechol.
BetaineThe risk or severity of adverse effects can be increased when Betaine is combined with Bethanechol.
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Bethanechol.
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Bethanechol.
Botulinum toxin type AThe risk or severity of hypotension can be increased when Botulinum toxin type A is combined with Bethanechol.
Botulinum toxin type BThe risk or severity of hypotension can be increased when Botulinum toxin type B is combined with Bethanechol.
Interactions
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Food Interactions
  • Take on an empty stomach. Nausea and vomiting may occur if taken after food.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Bethanechol chlorideH4QBZ2LO84590-63-6XXRMYXBSBOVVBH-UHFFFAOYSA-N
Product Images
International/Other Brands
Duvoid (Roberts) / Myotonachol (Glenwood) / Myotonine / Uro-Carb (Hamilton)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Duvoid Tablets 10 mgTablet10 mgOralPaladin Labs Inc1992-12-31Not applicableCanada flag
Duvoid Tablets 25 mgTablet25 mgOralPaladin Labs Inc1992-12-31Not applicableCanada flag
Duvoid Tablets 50 mgTablet50 mgOralPaladin Labs Inc1992-12-31Not applicableCanada flag
Myotonachol Tablets 10mgTablet10 mgOralGlenwood Inc.1993-12-312010-07-16Canada flag
Myotonachol Tablets 25mgTablet25 mgOralGlenwood Inc.1993-12-312010-07-16Canada flag
Urecholine Inj 5mg/mlLiquid5 mg / mLSubcutaneousMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1976-12-312003-01-31Canada flag
Urecholine Tab 10mgTablet10 mg / tabOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1976-12-312001-03-21Canada flag
Urecholine Tab 25mgTablet25 mg / tabOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1976-12-312001-01-25Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Bethanechol ChlorideTablet25 mg/1OralWockhardt2003-09-29Not applicableUS flag
Bethanechol ChlorideTablet10 mg/1OralImpax Generics2007-05-012013-12-31US flag
Bethanechol ChlorideTablet50 mg/1OralTeva Pharmaceuticals USA, Inc.1990-09-302021-03-31US flag50111 0326 01 nlmimage10 9c2f4e4a
Bethanechol ChlorideTablet5 mg/1OralHeritage Pharmaceuticals Inc.2010-05-04Not applicableUS flag
Bethanechol ChlorideTablet10 mg/1OralAmneal Pharmaceuticals LLC2007-11-21Not applicableUS flag
Bethanechol ChlorideTablet5 mg/1OralRising Pharmaceuticals2010-08-24Not applicableUS flag
Bethanechol ChlorideTablet10 mg/1OralActavis Totowa LLC2002-07-302010-07-30US flag
Bethanechol ChlorideTablet5 mg/1OralAvera McKennan Hospital2015-03-192017-05-24US flag
Bethanechol ChlorideTablet25 mg/1OralAmerincan Health Packaging2007-02-202015-09-30US flag
Bethanechol ChlorideTablet5 mg/1OralTeva Pharmaceuticals USA, Inc.1990-09-302021-02-28US flag50111 0323 01 nlmimage10 aa2f556a

Categories

ATC Codes
N07AB02 — Bethanechol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Quaternary ammonium salts
Direct Parent
Tetraalkylammonium salts
Alternative Parents
Carboximidic acids and derivatives / Organopnictogen compounds / Organooxygen compounds / Organic salts / Imines / Hydrocarbon derivatives / Amines / Organic cations
Substituents
Aliphatic acyclic compound / Amine / Carboximidic acid derivative / Hydrocarbon derivative / Imine / Organic cation / Organic oxygen compound / Organic salt / Organooxygen compound / Organopnictogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
carbamate ester, quaternary ammonium ion (CHEBI:3084)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
004F72P8F4
CAS number
674-38-4
InChI Key
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

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 References
  1. Padda IS, Derian A: Bethanechol . [Article]
  2. Bui T, Duong H: Muscarinic Agonists . [Article]
  3. Pakala RS, Brown KN, Preuss CV: Cholinergic Medications . [Article]
  4. DailyMed Drug Label Information: Bethanechol chloride oral tablets [Link]
Human Metabolome Database
HMDB0015154
KEGG Compound
C06850
PubChem Compound
2370
PubChem Substance
46507707
ChemSpider
2280
BindingDB
39342
RxNav
19257
ChEBI
3084
ChEMBL
CHEMBL1482
Therapeutic Targets Database
DAP000263
PharmGKB
PA448613
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bethanechol
AHFS Codes
  • 12:04.00 — Parasympathomemetic (Cholinergic) Agents
MSDS
Download (74.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedPreventionBladder Dysfunction1
2TerminatedTreatmentEosinophilic Esophagitis (EoE)1
1CompletedBasic ScienceType 2 Diabetes Mellitus1
1CompletedTreatmentEsophageal Dysmotility1
0RecruitingOtherMalignant Neoplasm of Pancreas1

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
  • Actavis Group
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Ascend Laboratories LLC
  • Caraco Pharmaceutical Labs
  • Duramed
  • Global Pharmaceuticals
  • Heartland Repack Services LLC
  • Impax Laboratories Inc.
  • Lannett Co. Inc.
  • Major Pharmaceuticals
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Pliva Inc.
  • QPharm Inc.
  • Ranbaxy Laboratories
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Sun Pharmaceutical Industries Ltd.
  • United Research Laboratories Inc.
  • USL Pharma Inc.
  • Vangard Labs Inc.
  • Wellspring Pharmaceutical
  • Wockhardt Ltd.
Dosage Forms
FormRouteStrength
TabletOral10 mg/1
TabletOral25 mg/1
TabletOral5 mg/1
TabletOral50 mg/1
TabletOral25 mg
TabletOral50 mg
TabletOral
LiquidSubcutaneous5 mg / mL
TabletOral10 mg / tab
TabletOral25 mg / tab
TabletOral10 mg
TabletOral5 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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
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...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
References
  1. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [Article]
  2. Padda IS, Derian A: Bethanechol . [Article]
  3. Bui T, Duong H: Muscarinic Agonists . [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Phosphatidylinositol phospholipase c 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...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
References
  1. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [Article]
  2. Padda IS, Derian A: Bethanechol . [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Padda IS, Derian A: Bethanechol . [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Guanyl-nucleotide exchange factor 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...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
References
  1. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [Article]
  2. Padda IS, Derian A: Bethanechol . [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Phosphatidylinositol phospholipase c 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...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
References
  1. Padda IS, Derian A: Bethanechol . [Article]

Drug created on June 13, 2005 13:24 / Updated on June 13, 2021 16:24