CHEBI:4639 - diphenoxylate

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ChEBI Name diphenoxylate
ChEBI ID CHEBI:4639
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
InChIKey HYPPXZBJBPSRLK-UHFFFAOYSA-N
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.
View more via ChEBI Ontology
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)
IUPAC Name
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
C07872 KEGG COMPOUND
D07861 KEGG DRUG
DB01081 DrugBank
Diphenoxylate Wikipedia
HMDB0015213 HMDB
LSM-5534 LINCS
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.