CHEBI:4534 - difenoxin

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ChEBI Name difenoxin
ChEBI ID CHEBI:4534
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C28H28N2O2
Net Charge 0
Average Mass 424.53410
Monoisotopic Mass 424.21508
InChI InChI=1S/C28H28N2O2/c29-22-28(24-12-6-2-7-13-24,25-14-8-3-9-15-25)18-21-30-19-16-27(17-20-30,26(31)32)23-10-4-1-5-11-23/h1-15H,16-21H2,(H,31,32)
InChIKey UFIVBRCCIRTJTN-UHFFFAOYSA-N
SMILES OC(=O)C1(CCN(CC1)CCC(C#N)(c1ccccc1)c1ccccc1)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): antidiarrhoeal drug
Any drug found useful in the symptomatic treatment of diarrhoea.
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ChEBI Ontology
Outgoing difenoxin (CHEBI:4534) has role antidiarrhoeal drug (CHEBI:55323)
difenoxin (CHEBI:4534) is a nitrile (CHEBI:18379)
difenoxin (CHEBI:4534) is a piperidinemonocarboxylic acid (CHEBI:26148)
difenoxin (CHEBI:4534) is a tertiary amine (CHEBI:32876)
Incoming diphenoxylate (CHEBI:4639) has functional parent difenoxin (CHEBI:4534)
difenoxin hydrochloride (CHEBI:59790) has part difenoxin (CHEBI:4534)
IUPAC Name
1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylic acid
INNs Sources
difenoxin ChemIDplus
difenoxina ChemIDplus
difenoxinum ChemIDplus
Synonyms Sources
1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotic acid ChemIDplus
Difenoxin KEGG COMPOUND
diphenoxilic acid NIST Chemistry WebBook
diphenoxylic acid ChemIDplus
Manual Xrefs Databases
878 DrugCentral
C07871 KEGG COMPOUND
D03809 KEGG DRUG
DB01501 DrugBank
DE1953342 Patent
Difenoxin Wikipedia
US3646207 Patent
View more database links
Registry Numbers Types Sources
28782-42-5 CAS Registry Number NIST Chemistry WebBook
28782-42-5 CAS Registry Number ChemIDplus
6827931 Beilstein Registry Number Beilstein
Last Modified
22 February 2017
General Comment
2011-05-09 The principal active metabolite of diphenoxylate, difenoxin has similar actions and uses, being administered as the hydrochloride for the symptomatic treatment of acute and chronic diarrhoea. In an attempt to discourage abuse (at high doses, difenoxin acts like morphine), preparations usually contain subclinical amounts of atropine sulfate.