Identification

Name
Bethanechol
Accession Number
DB01019  (APRD00051)
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
  • (2-hydroxypropyl)trimethylammonium carbamate
  • 2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
  • 2-carbamoyloxypropyl-trimethylazanium
  • Amidopropyldimethylbetaine
  • Carbamoyl-beta-methylcholine
  • carbamoyl-β-methylcholine
  • Carbamyl-beta-methylcholine
  • carbamyl-β-methylcholine
Product Ingredients
IngredientUNIICASInChI Key
Bethanechol ChlorideH4QBZ2LO84590-63-6XXRMYXBSBOVVBH-UHFFFAOYSA-N
Product Images
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 Inc.1993-12-312010-07-16Canada
Myotonachol Tablets 25mgTablet25 mgOralGlenwood Inc.1993-12-312010-07-16Canada
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
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bethanechol ChlorideTablet50 mg/1OralWockhardt2003-09-29Not applicableUs64679 0968 01 nlmimage10 7939bc9d
Bethanechol ChlorideTablet25 mg/1OralWockhardt2003-09-29Not applicableUs
Bethanechol ChlorideTablet25 mg/1OralLake Erie Medical DBAQuality Care Products LLC2015-08-062016-06-01Us
Bethanechol ChlorideTablet10 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2009-04-302016-12-30Us57664 0104 88 nlmimage10 0b0405b0
Bethanechol ChlorideTablet25 mg/1OralActavis South Atlantic LLC2004-07-212007-05-21Us
Bethanechol chlorideTablet5 mg/1OralActavis Totowa LLC2002-07-302010-07-30Us
Bethanechol ChlorideTablet10 mg/1OralRising Pharmaceuticals2010-04-06Not applicableUs
Bethanechol ChlorideTablet5 mg/1OralAmneal Pharmaceuticals of New York Llc2007-11-21Not applicableUs
Bethanechol ChlorideTablet5 mg/1OralImpax Generics2007-05-012013-12-31Us
Bethanechol ChlorideTablet50 mg/1OralTeva Pharmaceuticals USA, Inc.1990-09-30Not applicableUs50111 0326 01 nlmimage10 9c2f4e4a
International/Other Brands
Duvoid (Roberts) / Myotonachol (Glenwood) / Myotonine / Urabeth / Uro-Carb (Hamilton)
Categories
UNII
004F72P8F4
CAS number
674-38-4
Weight
Average: 161.2221
Monoisotopic: 161.129002798
Chemical Formula
C7H17N2O2
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

Pharmacology

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
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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M2
agonist
Human
UMuscarinic acetylcholine receptor M1Not AvailableHuman
UMuscarinic acetylcholine receptor M3Not AvailableHuman
UMuscarinic acetylcholine receptor M4Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Bethanechol.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Bethanechol.
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol 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.
AnisodamineThe risk or severity of adverse effects can be increased when Anisodamine is combined with Bethanechol.
ApramycinThe therapeutic efficacy of Bethanechol can be decreased when used in combination with Apramycin.
ArbekacinThe therapeutic efficacy of Bethanechol can be decreased when used in combination with Arbekacin.
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Bethanechol.
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Bethanechol.
Food Interactions
  • Take on empty stomach: 1 hour before or 2 hours after meals to avoid nausea.

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
ChEBI
3084
ChEMBL
CHEMBL1482
Therapeutic Targets Database
DAP000263
PharmGKB
PA448613
IUPHAR
297
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Bethanechol
ATC Codes
N07AB02 — Bethanechol
AHFS Codes
  • 12:04.00 — Parasympathomemetic (Cholinergic) Agents
MSDS
Download (74.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingOtherMalignant Neoplasm of Pancreas1
1CompletedBasic ScienceType 2 Diabetes Mellitus1
1CompletedTreatmentEsophageal Dysmotility1
2TerminatedTreatmentEosinophilic Esophagitis (EoE)1
4Not Yet RecruitingPreventionBladder Dysfunction1

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
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)about 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 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

Taxonomy

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
Tetraalkylammonium salt / Carboximidic acid derivative / Organic oxygen compound / Organopnictogen compound / Hydrocarbon derivative / Organic salt / Organooxygen compound / Imine / Amine / Organic cation
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
carbamate ester, quaternary ammonium ion (CHEBI:3084)

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...
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. [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]
Kind
Protein
Organism
Human
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
  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. [PubMed:9224827]
Kind
Protein
Organism
Human
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
  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. [PubMed:9224827]
Kind
Protein
Organism
Human
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
  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. [PubMed:9224827]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 05:32