CHEBI:4639 - diphenoxylate

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ChEBI Name diphenoxylate
Definition A piperidinecarboxylate ester that is the ethyl ester of difenoxin.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C30H32N2O2
Net Charge 0
Average Mass 452.58730
Monoisotopic Mass 452.246
InChI InChI=1S/C30H32N2O2/c1-2-34-28(33)29(25-12-6-3-7-13-25)18-21-32(22-19-29)23-20-30(24-31,26-14-8-4-9-15-26)27-16-10-5-11-17-27/h3-17H,2,18-23H2,1H3
SMILES CCOC(=O)C1(CCN(CC1)CCC(C#N)(c1ccccc1)c1ccccc1)c1ccccc1
Roles Classification
Chemical Role(s): 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 diphenoxylate (CHEBI:4639) has functional parent difenoxin (CHEBI:4534)
diphenoxylate (CHEBI:4639) has role antidiarrhoeal drug (CHEBI:55323)
diphenoxylate (CHEBI:4639) is a ethyl ester (CHEBI:23990)
diphenoxylate (CHEBI:4639) is a nitrile (CHEBI:18379)
diphenoxylate (CHEBI:4639) is a piperidinecarboxylate ester (CHEBI:48630)
diphenoxylate (CHEBI:4639) is a tertiary amine (CHEBI:32876)
Incoming diphenoxylate hydrochloride (CHEBI:59784) has part diphenoxylate (CHEBI:4639)
ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carboxylate
INNs Sources
difenoxilato ChemIDplus
diphenoxylate ChemIDplus
diphenoxylatum ChemIDplus
Synonyms Sources
1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-isonipecotic acid ethyl ester NIST Chemistry WebBook
2,2-diphenyl-4-(4-carbethoxy-4-phenylpiperidino)butyronitrile ChemIDplus
4-ethoxycarbonyl-α,α,4-triphenyl-1-piperidinebutyronitrile ChEBI
ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenyl-4-piperidinecarboxylate NIST Chemistry WebBook
ethyl 1-(3-cyano-3,3-diphenylpropyl)-4-phenylisonipecotate ChemIDplus
Manual Xrefs Databases
918 DrugCentral
DB01081 DrugBank
Diphenoxylate Wikipedia
HMDB0015213 HMDB
US2898340 Patent
View more database links
Registry Numbers Types Sources
503374 Reaxys Registry Number Reaxys
503374 Beilstein Registry Number Beilstein
915-30-0 CAS Registry Number ChemIDplus
915-30-0 CAS Registry Number NIST Chemistry WebBook
Last Modified
22 February 2017
General Comment
2011-05-09 A synthetic derivative of meperidine with little or no analgesic activity, diphenoxylate reduces intestinal motility and is used as the hydrochloride in the symptomatic treatment of acute and chronic diarrhoea; its active metabolite is the corresponding carboxylic acid, difenoxin. In an attempt to discourage abuse (at high doses, diphenoxylate acts like morphine), preparations usually contain subclinical amounts of atropine sulfate.