Bethanechol
Identification
- Name
- Bethanechol
- Accession Number
- DB01019
- 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.
- 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
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:Accelerate your drug discovery research with our fully connected ADMET dataset- Indication
For the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.
- Associated Conditions
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Bethanechol 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 action
Bethanechol 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.
Target Actions Organism AMuscarinic acetylcholine receptor M2 agonistHumans UMuscarinic acetylcholine receptor M1 Not Available Humans UMuscarinic acetylcholine receptor M3 Not Available Humans UMuscarinic acetylcholine receptor M4 Not Available Humans - Absorption
- Not Available
- 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
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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 Glycine 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. Capreomycin The therapeutic efficacy of Bethanechol can be decreased when used in combination with Capreomycin. Capsaicin The risk or severity of adverse effects can be increased when Capsaicin is combined with Bethanechol. 
Improve patient outcomesBuild effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.Learn more - Food Interactions
- Take on an empty stomach. Take at least 1 hour before or 2 hours after meals to avoid nausea.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- 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 Tablets 10 mg Tablet Oral Paladin Labs Inc 1992-12-31 Not applicable Canada 
Duvoid Tablets 25 mg Tablet Oral Paladin Labs Inc 1992-12-31 Not applicable Canada Duvoid Tablets 50 mg Tablet Oral Paladin Labs Inc 1992-12-31 Not applicable Canada Myotonachol Tablets 10mg Tablet Oral Glenwood Inc. 1993-12-31 2010-07-16 Canada Myotonachol Tablets 25mg Tablet Oral Glenwood Inc. 1993-12-31 2010-07-16 Canada Urecholine Inj 5mg/ml Liquid Subcutaneous Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1976-12-31 2003-01-31 Canada Urecholine Tab 10mg Tablet Oral Merck Frosst Canada & Cie, Merck Frosst Canada & Co. 1976-12-31 2001-03-21 Canada Urecholine Tab 25mg Tablet 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 5 mg/1 Oral Avera McKennan Hospital 2015-03-19 2017-05-24 US 
Bethanechol Chloride Tablet 25 mg/1 Oral Actavis South Atlantic LLC 2004-07-21 2007-05-21 US Bethanechol Chloride Tablet 5 mg/1 Oral Teva Pharmaceuticals USA, Inc. 1990-09-30 2021-02-28 US 
Bethanechol Chloride Tablet 5 mg/1 Oral Major Pharmaceuticals 2010-04-01 2011-10-24 US Bethanechol Chloride Tablet 50 mg/1 Oral Impax Generics 2007-05-01 2013-12-31 US Bethanechol Chloride Tablet 5 mg/1 Oral Rising Pharmaceuticals 2010-08-24 Not applicable US Bethanechol Chloride Tablet 10 mg/1 Oral Marlex Pharmaceuticals Inc 2015-04-01 Not applicable US Bethanechol Chloride Tablet 10 mg/1 Oral Golden State Medical Supply, Inc. 2012-04-02 2013-09-30 US Bethanechol Chloride Tablet 25 mg/1 Oral Actavis Totowa LLC 2002-07-30 2008-08-20 US Bethanechol Chloride Tablet 10 mg/1 Oral Lannett Company, Inc. 2008-03-27 Not applicable 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)
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
- Not Available
- 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
- AHFS Codes
- 12:04.00 — Parasympathomemetic (Cholinergic) Agents
- MSDS
- Download (74.1 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Bladder Dysfunction 1 2 Terminated Treatment Eosinophilic Esophagitis (EoE) 1 1 Completed Basic Science Type 2 Diabetes Mellitus 1 1 Completed Treatment Esophageal Dysmotility 1 0 Recruiting Other Malignant Neoplasm of Pancreas 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 10 mg Tablet Oral 25 mg Tablet Oral Tablet Oral 5 MG Liquid Subcutaneous - 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
Property Value Source melting point (°C) about 220 Major, R.T. and Bonnett, H.T.; U.S. Patent 2,322,375: June 22,1943; assigned to Merck & Co., Inc. water solubility 10 mg/mL (chloride salt) 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
- 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. [PubMed:17139284]
- 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]
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- 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. [PubMed:9224827]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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. [PubMed:9224827]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- 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. [PubMed:9224827]
Drug created on June 13, 2005 13:24 / Updated on February 24, 2021 19:34