Difenoxin
Basic information
- CAS
28782-42-5- Standard SMILES
N#CC(CCN1CCC(C(=O)O)(c2ccccc2)CC1)(c1ccccc1)c1ccccc1- InChIKey
UFIVBRCCIRTJTN-UHFFFAOYSA-N- Molecular formula
- C28H28N2O2
- Average molar mass
- 424.5 g/mol
- Monoisotopic mass
- 424.21507814
Overview
Difenoxin is a piperidinemonocarboxylic acid that is 4-phenylpiperidine-4-carboxylic acid in which the hydrogen attached to the nitrogen atom is substituted by a 3-cyano-3,3-diphenylpropyl group. It has a role as an antidiarrhoeal drug. It is a nitrile, a piperidinemonocarboxylic acid and a tertiary amine.
Names & identifiers
- Preferred name
- Difenoxin
- IUPAC
- 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid
Names & synonyms
DifenoxinDiphenoxylic acidDifenoxineDifenoxinaDifenoxinum28782-42-5diphenoxilic acid1-(3-Cyano-3,3-diphenylpropyl)-4-phenylisonipecotic acid1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acidMCN-JR-15,403-11Acscn-91683ZZ5BJ9F2Q
Show more names
McN-JR 15,403-11IDS-ND-007R-15403 FREE BASE4-Piperidinecarboxylic acid, 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-R 15,403 FREE BASEMcN-JR 15403-11CHEBI:4534DTXSID0022931
Database identifiers
- CAS
28782-42-5- PubChem CID
- 34328
- DTXSID
DTXSID0022931- ChEMBL
CHEMBL1201321- ChEBI
CHEBI:4534- UNII
- 3ZZ5BJ9F2Q
- Nikkaji
- J21.376D
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 64.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 636
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Narcotics
DEA Schedule I Controlled Substance -> Opiates
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationDEA schedule I controlled substance
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
Difenoxin acts as a potent antidiarrheal by slowing the movement of the intestines. It also crosses the blood brain barrier to a slight degree to exert weak sedative and analgesic effects. Adverse reactions thus include dizziness, drowsiness, lightheadedness and headache, in addition to gastrointestal side effects such as nausea, vomiting, dry mouth and epigastric distress. [Lexicomp, 2013]
Mechanism of Action
Difenoxin acts as an antidiarrheal by activating peripheral opioid receptors in the small intestine and thereby inhibiting peristalsis. However, research has suggested that non-opioid receptor pathways exist. This would explain the potent antidiarrheal effects of difenoxin despite only limited opioid action [1].
Biological Half-LifeThe elimination half life was calculated to be 7.24 hours. The appearance half life was calculated to be 0.82h. [3]
Metabolism/MetabolitesMetabolism occurs by hydroxylation to form an inactive metabolite. [Lexicomp, 2013]
FDA Pharmacological Classification
3ZZ5BJ9F2Q
DIFENOXIN
Established Pharmacologic Class [EPC] - Antidiarrheal
Difenoxin is an Antidiarrheal.
Absorption, Distribution and Excretion
A high percentage of Motofen(R) is absorbed, and absorption occurs rapidly. Peak plasma concentrations are achieved within 40-60 minutes. [Lexicomp, 2013]
Both the drug and its metabolites are excreted, mainly as conjugates, in urine and feces. [Lexicomp, 2012]
Related reactions
8 records
Compound notes
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