Details of the Drug

General Information of Drug (ID: DMCLHO0)

Drug Name

Bethanechol

Synonyms

Amidopropyldimethylbetaine; Bethanecol; Urabeth; Myotonine chloride; Duvoid (TN); Myotonachol (TN); Urecholine (TN); Carbamoyl-beta-methylcholine; Carbamyl-beta-methylcholine; Ammonium, (2-hydroxypropyl)trimethyl-, carbamate (ester); (2-Hydroxypropyl)trimethylammonium carbamate; 1-Propanaminium, 2-((aminocarbonyl)oxy)-N,N,N-trimethyl-(9CI); 2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propanaminium; 2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium; 2-carbamoyloxypropyl(trimethyl)azanium; 2-carbamoyloxypropyl-trimethylazanium

Indication

Disease Entry	ICD 11	Status	REF
Urinary retention	MF50.3	Approved	[1]

Therapeutic Class

Parasympathomimetics

Affected Organisms

Humans and other mammals

ATC Code

N07AB02: Bethanechol

N07AB: Choline esters

N07A: PARASYMPATHOMIMETICS

N07: OTHER NERVOUS SYSTEM DRUGS

N: NERVOUS SYSTEM

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

161.22

Logarithm of the Partition Coefficient (xlogp)

0

Rotatable Bond Count (rotbonds)

4

Hydrogen Bond Donor Count (hbonddonor)

1

Hydrogen Bond Acceptor Count (hbondacc)

2

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [2]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 14.5269 micromolar/kg/day [3]

Chemical Identifiers

Formula: C7H17N2O2+
IUPAC Name: 2-carbamoyloxypropyl(trimethyl)azanium
Canonical SMILES: CC(C[N+](C)(C)C)OC(=O)N
InChI: InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
InChIKey: NZUPCNDJBJXXRF-UHFFFAOYSA-O

Cross-matching ID

PubChem CID: 2370
ChEBI ID: CHEMBL1482
CAS Number: 674-38-4
UNII: 004F72P8F4
DrugBank ID: DB01019
TTD ID: D07ZTO
ACDINA ID: D00066

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Muscarinic acetylcholine receptor M5 (CHRM5)	TTH18TF	ACM5_HUMAN	Agonist	[4]

Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Bethanechol (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Umeclidinium	DM4E8O9	Moderate	Antagonize the effect of Bethanechol when combined with Umeclidinium.	Chronic obstructive pulmonary disease [CA22]	[5]
Tiotropium	DMFDC0Q	Moderate	Antagonize the effect of Bethanechol when combined with Tiotropium.	Chronic obstructive pulmonary disease [CA22]	[5]
Revefenacin	DMMP5SI	Moderate	Antagonize the effect of Bethanechol when combined with Revefenacin.	Chronic obstructive pulmonary disease [CA22]	[5]
Mepenzolate	DM8YU2F	Moderate	Antagonize the effect of Bethanechol when combined with Mepenzolate.	Digestive system disease [DE2Z]	[5]
Oxybutynine	DMJPBAX	Moderate	Antagonize the effect of Bethanechol when combined with Oxybutynine.	Discovery agent [N.A.]	[5]
Solifenacin	DMG592Q	Moderate	Antagonize the effect of Bethanechol when combined with Solifenacin.	Functional bladder disorder [GC50]	[5]
Tolterodine	DMSHPW8	Moderate	Antagonize the effect of Bethanechol when combined with Tolterodine.	Functional bladder disorder [GC50]	[5]
Belladonna	DM2RBWK	Moderate	Antagonize the effect of Bethanechol when combined with Belladonna.	Infectious gastroenteritis/colitis [1A40]	[5]
Polyethylene glycol	DM4I1JP	Moderate	Increased risk of lowers seizure threshold by the combination of Bethanechol and Polyethylene glycol.	Irritable bowel syndrome [DD91]	[6]
Neostigmine	DM6T2J3	Moderate	Additive cholinergic effects by the combination of Bethanechol and Neostigmine.	Myasthenia gravis [8C6Y]	[7]
Cyclizine	DM9G7BS	Moderate	Antagonize the effect of Bethanechol when combined with Cyclizine.	Nausea/vomiting [MD90]	[5]
Bupropion	DM5PCS7	Major	Increased risk of lowers seizure threshold by the combination of Bethanechol and Bupropion.	Nicotine use disorder [6C4A]	[8]
Flavoxate	DMKV4NL	Moderate	Antagonize the effect of Bethanechol when combined with Flavoxate.	Pain [MG30-MG3Z]	[5]
Methylscopolamine	DM5VWOB	Moderate	Antagonize the effect of Bethanechol when combined with Methylscopolamine.	Peptic ulcer [DA61]	[5]
Procainamide	DMNMXR8	Moderate	Antagonize the effect of Bethanechol when combined with Procainamide.	Ventricular tachyarrhythmia [BC71]	[5]


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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
Hydrazine yellow	E00409	164825	Colorant
Quinoline yellow WS	E00309	24671	Colorant
Sunset yellow FCF	E00255	17730	Colorant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant


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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Bethanechol 25 mg tablet	25 mg	Oral Tablet	Oral
Bethanechol 50 mg tablet	50 mg	Oral Tablet	Oral
Bethanechol 10 mg tablet	10 mg	Oral Tablet	Oral
Bethanechol 5 mg tablet	5 mg	Oral Tablet	Oral

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 297).
2	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4	Loss of Ca-mediated ion transport during colitis correlates with reduced ion transport responses to a Ca-activated K channel opener. Br J Pharmacol. 2009 Apr;156(7):1085-97.
5	Benjamin KW "Toxicity of ocular medications." Int Ophthalmol Clin 19 (1979): 199-255. [PMID: 376469]
6	Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
7	Product Information. Aricept (donepezil). Pfizer US Pharmaceuticals, New York, NY.
8	Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.