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Bethanechol

PubChem CID
2370
Structure
Bethanechol_small.png
Bethanechol_3D_Structure.png
Molecular Formula
Synonyms
  • bethanechol
  • 674-38-4
  • Amidopropyldimethylbetaine
  • Carbamyl-beta-methylcholine
  • Carbamoyl-beta-methylcholine
Molecular Weight
161.22 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-11
Description
Bethanechol is the carbamic acid ester of 2-methylcholine. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used as its chloride salt to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention. It has a role as a muscarinic agonist. It is a quaternary ammonium ion and a carbamate ester.
Bethanechol is a synthetic ester that was initially synthesized in 1935. 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. 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.
Bethanechol is a Cholinergic Muscarinic Agonist. The mechanism of action of bethanechol is as a Cholinergic Muscarinic Agonist.
See also: Bethanechol Chloride (has salt form).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Bethanechol.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-carbamoyloxypropyl(trimethyl)azanium
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

NZUPCNDJBJXXRF-UHFFFAOYSA-O
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

CC(C[N+](C)(C)C)OC(=O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C7H17N2O2+
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 PharmGKB ID

2.3.14 Pharos Ligand ID

2.3.15 RXCUI

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Bethanechol
  • Bethanechol Chloride
  • Bethanecol
  • Chloride, Bethanechol
  • Duvoid
  • Hermes, Myo
  • Myo Hermes
  • Myocholine
  • Myotonachol
  • Myotonine
  • PMS Bethanechol Chloride
  • PMS-Bethanechol Chloride
  • Urecholine
  • Urocarb

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
161.22 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
0
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
161.129002789 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
161.129002789 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
52.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
11
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
1
Reference
Computed by PubChem
Property Name
Complexity
Property Value
140
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Solid

3.2.2 Melting Point

217 - 221 °C (chloride salt)

3.2.3 Solubility

3.11e-01 g/L

3.2.4 Collision Cross Section

131.37 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Muscarinic Agonists; Parasympathomimetics
3.3.1.2 Animal Drugs
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug 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.

6.2 Drug Classes

Breast Feeding; Lactation; Muscarinic Agonists; Parasympathomimetics

6.3 Clinical Trials

6.3.1 ClinicalTrials.gov

7 Pharmacology and Biochemistry

7.1 Pharmacodynamics

Bethanechol is selective for muscarinic receptors and has little to no impact on nicotinic receptors. 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.

7.2 MeSH Pharmacological Classification

Parasympathomimetics
Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)
Muscarinic Agonists
Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)

7.3 FDA Pharmacological Classification

FDA UNII
004F72P8F4
Active Moiety
BETHANECHOL
Pharmacological Classes
Established Pharmacologic Class [EPC] - Cholinergic Muscarinic Agonist
Pharmacological Classes
Mechanisms of Action [MoA] - Cholinergic Muscarinic Agonists
FDA Pharmacology Summary
Bethanechol is a Cholinergic Muscarinic Agonist. The mechanism of action of bethanechol is as a Cholinergic Muscarinic Agonist.

7.4 ATC Code

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N07 - Other nervous system drugs

N07A - Parasympathomimetics

N07AB - Choline esters

N07AB02 - Bethanechol

7.5 Absorption, Distribution and Excretion

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. 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.

7.6 Mechanism of Action

Bethanechol is a direct muscarinic agonist and stimulates the parasympathetic nervous system by binding to postganglionic muscarinic receptors. 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. 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. As a result of selectivity for muscarinic receptors, bethanechol produces minimal to no nicotinic effects.

7.7 Human Metabolite Information

7.7.1 Cellular Locations

Membrane

8 Use and Manufacturing

8.1 Uses

Use (kg; approx.) in Germany (2009): >100

Consumption (g per capita; approx.) in Germany (2009): 0.00122

Calculated removal (%): 75.1

For the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.

8.1.1 Use Classification

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

9 Toxicity

9.1 Toxicological Information

9.1.1 Toxicity Summary

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.

9.1.2 Drug Induced Liver Injury

Compound
bethanechol
DILI Annotation
No-DILI-Concern
Label Section
No match
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

9.1.3 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

9.1.4 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the use of bethanechol during breastfeeding. If it is used during breastfeeding, monitor the infant for signs of cholinergic excess (diarrhea, lacrimation, and excessive salivation or urination), especially in younger, exclusively breastfed infants.

◉ Effects in Breastfed Infants

Relevant published information was not found as of the revision date.

◉ Effects on Lactation and Breastmilk

Relevant published information in nursing mothers was not found as of the revision date. In animals, cholinergic drugs increase oxytocin release, and have variable effects on serum prolactin. The prolactin level in a mother with established lactation may not affect her ability to breastfeed.

9.1.5 Exposure Routes

Oral

9.1.6 Acute Effects

9.1.7 Treatment

Atropine Sulfate is a specific antidote. The recommended dose for adults is 0.6 mg. Repeat doses can be given every two hours, according to clinical response. The recommended dosage in infants and children up to 12 years of age is 0.01 mg/kg (to a maximum single dose of 0.4 mg) repeated every two hours as needed until the desired effect is obtained or adverse effects of atropine preclude further usage. Subcutaneous injection of atropine is preferred except in emergencies when the intravenous route may be employed. (L1712)
L1712: RxList: The Internet Drug Index (2009). http://www.rxlist.com/

10 Associated Disorders and Diseases

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Chemical Co-Occurrences in Literature

11.4 Chemical-Gene Co-Occurrences in Literature

11.5 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

13.2 Drug-Drug Interactions

13.3 Drug-Food Interactions

Take on an empty stomach. Nausea and vomiting may occur if taken after food.

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChEBI Ontology

15.4 KEGG: ATC

15.5 KEGG: Risk Category of Japanese OTC Drugs

15.6 KEGG: Drug Groups

15.7 WHO ATC Classification System

15.8 FDA Pharm Classes

15.9 ChemIDplus

15.10 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

15.11 ChEMBL Target Tree

15.12 NORMAN Suspect List Exchange Classification

15.13 CCSBase Classification

15.14 EPA DSSTox Classification

15.15 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
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    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. FDA Global Substance Registration System (GSRS)
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  6. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  7. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  8. ChEBI
  9. FDA Pharm Classes
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. Open Targets
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    https://platform-docs.opentargets.org/licence
  11. Toxin and Toxin Target Database (T3DB)
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    http://www.t3db.ca/downloads
  12. ChEMBL
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    http://www.ebi.ac.uk/Information/termsofuse.html
  13. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  14. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  15. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  16. Therapeutic Target Database (TTD)
  17. Drug Induced Liver Injury Rank (DILIrank) Dataset
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  18. Drugs and Lactation Database (LactMed)
  19. Japan Chemical Substance Dictionary (Nikkaji)
  20. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
    Risk category of Japanese OTC drugs
    http://www.genome.jp/kegg-bin/get_htext?br08312.keg
  21. Metabolomics Workbench
  22. NCI Thesaurus (NCIt)
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    https://www.cancer.gov/policies/copyright-reuse
  23. NLM RxNorm Terminology
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  24. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    BETHANECHOL
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  25. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
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    https://www.whocc.no/copyright_disclaimer/
  26. PharmGKB
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    https://www.pharmgkb.org/page/policies
  27. Pharos
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  28. Wikidata
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  31. PubChem
  32. MolGenie
    MolGenie Organic Chemistry Ontology
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  33. PATENTSCOPE (WIPO)
  34. NCBI
CONTENTS