bethanechol ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
358 674-38-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • bethanechol
  • carbamoyl-beta-methylcholine
  • carbamyl-beta-methylcholine
  • liberan
  • bethanechol chloride
A slowly hydrolyzing 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, HEART RATE changes, and BRONCHIAL SPASM.
  • Molecular weight: 161.22
  • Formula: C7H17N2O2
  • CLOGP: -4.01
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 1
  • TPSA: 52.32
  • ALOGS: -2.80
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
45 mg O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 14.53 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Bocci G, Oprea TI, Benet LZ
S (Water solubility) 625.41 mg/mL Bocci G, Oprea TI, Benet LZ

Approvals:

DateAgencyCompanyOrphan
Oct. 12, 1948 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Peritonitis 36.12 23.89 13 1119 17141 63470749
Fall 25.49 23.89 33 1099 392301 63095589
Hypertensive nephropathy 25.34 23.89 5 1127 647 63487243

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Potentiating drug interaction 76.18 27.02 18 670 4959 34951284
Oesophageal rupture 60.62 27.02 10 678 429 34955814
Urinary tract infection 42.21 27.02 24 664 84057 34872186
Pancreatic failure 29.72 27.02 6 682 792 34955451

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Potentiating drug interaction 64.73 21.63 18 1650 8801 79733919
Oesophageal rupture 52.38 21.63 10 1658 929 79741791
Urinary tract infection 30.67 21.63 33 1635 274479 79468241
Peritonitis 27.92 21.63 13 1655 28023 79714697
Infective pulmonary exacerbation of cystic fibrosis 26.46 21.63 10 1658 12841 79729879
Pancreatic failure 25.07 21.63 6 1662 1622 79741098
Hypertensive nephropathy 22.34 21.63 5 1663 1009 79741711

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC N07AB02 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
PARASYMPATHOMIMETICS
Choline esters
FDA MoA N0000000104 Cholinergic Muscarinic Agonists
CHEBI has role CHEBI:38325 muscarinic agonists
FDA EPC N0000175840 Cholinergic Muscarinic Agonist
MeSH PA D018678 Cholinergic Agents
MeSH PA D018679 Cholinergic Agonists
MeSH PA D018721 Muscarinic Agonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010277 Parasympathomimetics
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Retention of urine indication 267064002
Urinary tract obstruction contraindication 7163005 DOID:5200
Irritable bowel syndrome contraindication 10743008 DOID:9778
Peptic ulcer contraindication 13200003 DOID:750
Increased gastric tonus contraindication 18644006
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Orthostatic hypotension contraindication 28651003
Parkinsonism contraindication 32798002
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Low blood pressure contraindication 45007003
Peritonitis contraindication 48661000
Bradycardia contraindication 48867003
Parkinson's disease contraindication 49049000 DOID:14330
Abnormal vasomotor function contraindication 70670009
Epilepsy contraindication 84757009 DOID:1826
Gastrointestinal obstruction contraindication 126765001
Asthma contraindication 195967001 DOID:2841
Atrioventricular block contraindication 233917008 DOID:0050820
Anastomosis of intestine contraindication 235407009
Bladder outflow obstruction contraindication 236645006
Operation on gastrointestinal tract contraindication 386621005
Disorder of coronary artery contraindication 414024009
Bladder Surgery contraindication




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M2 GPCR AGONIST Ki 4 IUPHAR CHEMBL
Muscarinic acetylcholine receptor M3 GPCR AGONIST Ki 4.20 IUPHAR CHEMBL
Muscarinic acetylcholine receptor M1 GPCR AGONIST Ki 4 IUPHAR
Muscarinic acetylcholine receptor M4 GPCR AGONIST Ki 4 IUPHAR
Muscarinic acetylcholine receptor GPCR Kd 4.90 CHEMBL
Muscarinic receptor 2 GPCR EC50 6 CHEMBL

External reference:

IDSource
4019634 VUID
N0000147727 NUI
D01000 KEGG_DRUG
590-63-6 SECONDARY_CAS_RN
19257 RXNORM
C0053526 UMLSCUI
CHEBI:3084 CHEBI
CHEMBL1482 ChEMBL_ID
DB01019 DRUGBANK_ID
CHEMBL1768 ChEMBL_ID
D018723 MESH_DESCRIPTOR_UI
2370 PUBCHEM_CID
297 IUPHAR_LIGAND_ID
004F72P8F4 UNII
3310 MMSL
4281 MMSL
d01427 MMSL
31178001 SNOMEDCT_US
31690003 SNOMEDCT_US
372698003 SNOMEDCT_US
4017938 VANDF
4019634 VANDF
001691 NDDF
004683 NDDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1329 TABLET 50 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1329 TABLET 50 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1332 TABLET 5 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1332 TABLET 5 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1340 TABLET 10 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1340 TABLET 10 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1356 TABLET 25 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0527-1356 TABLET 25 mg ORAL ANDA 17 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0510 TABLET 5 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0510 TABLET 5 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0511 TABLET 10 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0511 TABLET 10 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0512 TABLET 25 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0512 TABLET 25 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0513 TABLET 50 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0832-0513 TABLET 50 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6178 TABLET 25 mg ORAL ANDA 10 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-6178 TABLET 25 mg ORAL ANDA 10 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-516 TABLET 10 mg ORAL ANDA 18 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-517 TABLET 25 mg ORAL ANDA 18 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-518 TABLET 50 mg ORAL ANDA 18 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 50111-323 TABLET 5 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 50111-324 TABLET 10 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 50111-325 TABLET 25 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 50111-326 TABLET 50 mg ORAL ANDA 19 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 51293-645 TABLET 5 mg ORAL ANDA 10 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 51293-646 TABLET 10 mg ORAL ANDA 10 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 51293-647 TABLET 25 mg ORAL ANDA 10 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 51293-648 TABLET 50 mg ORAL ANDA 10 sections
Bethanechol Chloride HUMAN PRESCRIPTION DRUG LABEL 1 53746-571 TABLET 5 mg ORAL ANDA 10 sections