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], [2]
Therapeutic Class
Parasympathomimetics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 161.22
Topological Polar Surface Area (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 [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 14.5269 micromolar/kg/day [4]
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
CHEBI:3084
CAS Number
674-38-4
DrugBank ID
DB01019
TTD ID
D07ZTO
ACDINA ID
D00066

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 [5], [6], [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

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] [18]
Tiotropium DMFDC0Q Moderate Antagonize the effect of Bethanechol when combined with Tiotropium. Chronic obstructive pulmonary disease [CA22] [18]
Revefenacin DMMP5SI Moderate Antagonize the effect of Bethanechol when combined with Revefenacin. Chronic obstructive pulmonary disease [CA22] [18]
Mepenzolate DM8YU2F Moderate Antagonize the effect of Bethanechol when combined with Mepenzolate. Digestive system disease [DE2Z] [18]
Oxybutynine DMJPBAX Moderate Antagonize the effect of Bethanechol when combined with Oxybutynine. Discovery agent [N.A.] [18]
Solifenacin DMG592Q Moderate Antagonize the effect of Bethanechol when combined with Solifenacin. Functional bladder disorder [GC50] [18]
Tolterodine DMSHPW8 Moderate Antagonize the effect of Bethanechol when combined with Tolterodine. Functional bladder disorder [GC50] [18]
Belladonna DM2RBWK Moderate Antagonize the effect of Bethanechol when combined with Belladonna. Infectious gastroenteritis/colitis [1A40] [18]
Polyethylene glycol DM4I1JP Moderate Increased risk of lowers seizure threshold by the combination of Bethanechol and Polyethylene glycol. Irritable bowel syndrome [DD91] [19]
Neostigmine DM6T2J3 Moderate Additive cholinergic effects by the combination of Bethanechol and Neostigmine. Myasthenia gravis [8C6Y] [20]
Cyclizine DM9G7BS Moderate Antagonize the effect of Bethanechol when combined with Cyclizine. Nausea/vomiting [MD90] [18]
Bupropion DM5PCS7 Major Increased risk of lowers seizure threshold by the combination of Bethanechol and Bupropion. Nicotine use disorder [6C4A] [21]
Flavoxate DMKV4NL Moderate Antagonize the effect of Bethanechol when combined with Flavoxate. Pain [MG30-MG3Z] [18]
Methylscopolamine DM5VWOB Moderate Antagonize the effect of Bethanechol when combined with Methylscopolamine. Peptic ulcer [DA61] [18]
Procainamide DMNMXR8 Moderate Antagonize the effect of Bethanechol when combined with Procainamide. Ventricular tachyarrhythmia [BC71] [18]
⏷ Show the Full List of 15 DDI Information of This Drug

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
⏷ Show the Full List of 10 Pharmaceutical Excipients of This Drug
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
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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2 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040518.
3 BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
4 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
5 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.
6 Morphine increases acetylcholine release in the trigeminal nuclear complex. Sleep. 2008 Dec 1;31(12):1629-37.
7 Postoperative analgesia induced by intrathecal neostigmine or bethanechol in rats. Clin Exp Pharmacol Physiol. 2009 Jul;36(7):648-54.
8 Muscarinic cholinergic and histamine H1 receptor binding of phenothiazine drug metabolites. Life Sci. 1988;43(5):405-12.
9 Design, synthesis, and neurochemical evaluation of 5-(3-alkyl-1,2,4- oxadiazol-5-yl)-1,4,5,6-tetrahydropyrimidines as M1 muscarinic receptor agonists. J Med Chem. 1993 Apr 2;36(7):842-7.
10 Retinoic acid prevents virus-induced airway hyperreactivity and M2 receptor dysfunction via anti-inflammatory and antiviral effects. Am J Physiol Lung Cell Mol Physiol. 2009 Aug;297(2):L340-6.
11 Medicinal plants in therapy. Bull World Health Organ. 1985;63(6):965-81.
12 Additive protective effects of donepezil and nicotine against salsolinol-induced cytotoxicity in SH-SY5Y cells. Neurotox Res. 2009 Oct;16(3):194-204.
13 Affinity profiles of various muscarinic antagonists for cloned human muscarinic acetylcholine receptor (mAChR) subtypes and mAChRs in rat heart and submandibular gland. Life Sci. 1999;64(25):2351-8.
14 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: 7354).
15 Natural products as sources of new drugs over the last 25 years. J Nat Prod. 2007 Mar;70(3):461-77.
16 Comparison of pharmacological effects of L- and DL-n-butyl-scopolamine in rat uterus. Yao Xue Xue Bao. 1994;29(1):24-7.
17 Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
18 Benjamin KW "Toxicity of ocular medications." Int Ophthalmol Clin 19 (1979): 199-255. [PMID: 376469]
19 Product Information. Suprep Bowel Prep Kit (magnesium/potassium/sodium sulfates). Braintree Laboratories, Braintree, MA.
20 Product Information. Aricept (donepezil). Pfizer US Pharmaceuticals, New York, NY.
21 Product Information. Wellbutrin XL (buPROPion). GlaxoSmithKline, Philadelphia, PA.