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
Structure for Bethanechol (DB01019)
- 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
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- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Target Actions Organism AMuscarinic acetylcholine receptor M3 agonistHumans UMuscarinic acetylcholine receptor M1 agonistHumans UMuscarinic acetylcholine receptor M2 agonistHumans UMuscarinic acetylcholine receptor M4 agonistHumans UMuscarinic acetylcholine receptor M5 agonistHumans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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 = 0.4 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Bethanechol. Ambenonium The risk or severity of adverse effects can be increased when Ambenonium is combined with Bethanechol. Amikacin The therapeutic efficacy of Bethanechol can be decreased when used in combination with Amikacin. Aprotinin The risk or severity of adverse effects can be increased when Aprotinin is combined with Bethanechol. Atenolol The risk or severity of adverse effects can be increased when Atenolol is combined with Bethanechol. Betaine The risk or severity of adverse effects can be increased when Betaine is combined with Bethanechol. Betaxolol The risk or severity of adverse effects can be increased when Betaxolol is combined with Bethanechol. Bisoprolol The risk or severity of adverse effects can be increased when Bisoprolol is combined with Bethanechol. Botulinum toxin type A The risk or severity of hypotension can be increased when Botulinum toxin type A is combined with Bethanechol. Botulinum toxin type B The risk or severity of hypotension can be increased when Botulinum toxin type B is combined with Bethanechol. 
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- Take on an empty stomach. Nausea and vomiting may occur if taken after food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bethanechol chloride H4QBZ2LO84 590-63-6 XXRMYXBSBOVVBH-UHFFFAOYSA-N - Product Images
- International/Other Brands
- Duvoid (Roberts) / Myotonachol (Glenwood) / Myotonine / Uro-Carb (Hamilton)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Duvoid Tablet 10 mg Oral Paladin Labs Inc. 1992-12-31 Not applicable Canada 
Duvoid Tablet 25 mg Oral Paladin Labs Inc. 1992-12-31 Not applicable Canada Duvoid Tablet 50 mg Oral Paladin Labs Inc. 1992-12-31 Not applicable Canada Myotonachol Tablets 10mg Tablet 10 mg Oral Glenwood Inc. 1993-12-31 2010-07-16 Canada Myotonachol Tablets 25mg Tablet 25 mg Oral Glenwood Inc. 1993-12-31 2010-07-16 Canada Urecholine Inj 5mg/ml Liquid 5 mg / mL Subcutaneous Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1976-12-31 2003-01-31 Canada Urecholine Tab 10mg Tablet 10 mg / tab Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1976-12-31 2001-03-21 Canada Urecholine Tab 25mg Tablet 25 mg / tab Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1976-12-31 2001-01-25 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Bethanechol Chloride Tablet 25 mg/1 Oral Impax Generics 2007-05-01 2013-12-31 US 
Bethanechol Chloride Tablet 50 mg/1 Oral Heritage Pharmaceuticals Inc. 2010-05-04 Not applicable US Bethanechol Chloride Tablet 10 mg/1 Oral Wockhardt USA LLC. 2003-09-29 Not applicable US 
Bethanechol Chloride Tablet 25 mg/1 Oral Marlex Pharmaceuticals Inc 2015-04-01 Not applicable US Bethanechol Chloride Tablet 10 mg/1 Oral AvPAK 2010-12-30 2017-04-30 US Bethanechol Chloride Tablet 25 mg/1 Oral Remedy Repack 2013-09-19 2014-09-19 US Bethanechol Chloride Tablet 5 mg/1 Oral Heritage Pharmaceuticals Inc. 2010-05-04 Not applicable US Bethanechol Chloride Tablet 25 mg/1 Oral Eci Pharmaceuticals Llc 2020-02-15 Not applicable US Bethanechol Chloride Tablet 25 mg/1 Oral Wockhardt 2003-09-29 Not applicable US Bethanechol Chloride Tablet 50 mg/1 Oral AvKARE, Inc. 2010-04-01 2018-09-18 US
Categories
- ATC Codes
- N07AB02 — Bethanechol
- Drug Categories
- Acids, Acyclic
- Amines
- Ammonium Compounds
- Autonomic Agents
- Bethanechol Compounds
- Carbamates
- Choline Esters
- Cholinergic Agents
- Cholinergic Agonists
- Muscarinic Agonists
- Nervous System
- Neurotransmitter Agents
- Nitrogen Compounds
- Onium Compounds
- Parasympathomemetic (Cholinergic) Agents
- Parasympathomimetics
- Peripheral Nervous System Agents
- Quaternary Ammonium Compounds
- Trimethyl Ammonium Compounds
- 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
- External Links
- Human Metabolome Database
- HMDB0015154
- KEGG Compound
- C06850
- PubChem Compound
- 2370
- PubChem Substance
- 46507707
- ChemSpider
- 2280
- BindingDB
- 39342
- 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
- MSDS
- Download (74.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Bladder Dysfunction 1 2 Recruiting Other Malignant Neoplasm of Pancreas 1 2 Terminated Treatment Eosinophilic Esophagitis (EoE) 1 1 Completed Basic Science Type 2 Diabetes Mellitus 1 1 Completed Treatment Esophageal Motility Disorders 1 0 Recruiting Other Malignant Neoplasm of Pancreas 1 Not Available Not Yet Recruiting Not Available Tracheobronchomalacia 1
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
Form Route Strength Tablet Oral 10 mg/1 Tablet Oral 25 mg/1 Tablet Oral 5 mg/1 Tablet Oral 50 mg/1 Tablet Oral 25 mg Tablet Oral 50 mg Tablet Oral Liquid Subcutaneous 5 mg / mL Tablet Oral 10 mg / tab Tablet Oral 25 mg / tab Tablet Oral 10 mg Tablet Oral 5 mg - Prices
Unit description Cost Unit Bethanechol chloride powder 10.1USD g Urecholine 50 mg tablet 3.95USD tablet Urecholine 25 mg tablet 3.46USD tablet Bethanechol Chloride 50 mg tablet 2.97USD tablet Bethanechol 50 mg tablet 2.85USD tablet Bethanechol Chloride 25 mg tablet 1.86USD tablet Urecholine 10 mg tablet 1.85USD tablet Bethanechol 25 mg tablet 1.78USD tablet Bethanechol Chloride 10 mg tablet 1.39USD tablet Bethanechol 10 mg tablet 1.34USD tablet Urecholine 5 mg tablet 1.14USD tablet Bethanechol Chloride 5 mg tablet 0.74USD tablet Bethanechol 5 mg tablet 0.71USD 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
Property Value Source Water Solubility 0.311 mg/mL ALOGPS logP -2.8 ALOGPS logP -4.1 ChemAxon logS -2.8 ALOGPS pKa (Strongest Acidic) 15.34 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 52.32 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 54.44 m3·mol-1 ChemAxon Polarizability 17.73 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8407 Blood Brain Barrier + 0.9789 Caco-2 permeable + 0.5251 P-glycoprotein substrate Non-substrate 0.7295 P-glycoprotein inhibitor I Non-inhibitor 0.9508 P-glycoprotein inhibitor II Non-inhibitor 0.8371 Renal organic cation transporter Non-inhibitor 0.9209 CYP450 2C9 substrate Non-substrate 0.8304 CYP450 2D6 substrate Non-substrate 0.8066 CYP450 3A4 substrate Substrate 0.5216 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9522 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9047 Ames test Non AMES toxic 0.6804 Carcinogenicity Carcinogens 0.522 Biodegradation Not ready biodegradable 0.8058 Rat acute toxicity 2.7833 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9852 hERG inhibition (predictor II) Non-inhibitor 0.8915
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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]
- Padda IS, Derian A: Bethanechol . [Article]
- 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
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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]
- 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]
- 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]
- 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
- 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
- Padda IS, Derian A: Bethanechol . [Article]
Drug created at June 13, 2005 13:24 / Updated at May 28, 2022 06:24