CHEBI:101278 - diltiazem

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ChEBI Name diltiazem
ChEBI ID CHEBI:101278
Definition A 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate in which both stereocentres have S configuration. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:4602
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Formula C22H26N2O4S
Net Charge 0
Average Mass 414.51800
Monoisotopic Mass 414.161
InChI InChI=1S/C22H26N2O4S/c1-15(25)28-20-21(16-9-11-17(27-4)12-10-16)29-19-8-6-5-7-18(19)24(22(20)26)14-13-23(2)3/h5-12,20-21H,13-14H2,1-4H3/t20-,21+/m1/s1
InChIKey HSUGRBWQSSZJOP-RTWAWAEBSA-N
SMILES COc1ccc(cc1)[C@@H]1Sc2ccccc2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O
Roles Classification
Biological Role(s): calcium channel blocker
One of a class of drugs that acts by selective inhibition of calcium influx through cell membranes or on the release and binding of calcium in intracellular pools.
Application(s): vasodilator agent
A drug used to cause dilation of the blood vessels.
antihypertensive agent
Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing diltiazem (CHEBI:101278) has role antihypertensive agent (CHEBI:35674)
diltiazem (CHEBI:101278) has role calcium channel blocker (CHEBI:38215)
diltiazem (CHEBI:101278) has role vasodilator agent (CHEBI:35620)
diltiazem (CHEBI:101278) is a 5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate (CHEBI:82814)
diltiazem (CHEBI:101278) is conjugate base of diltiazem(1+) (CHEBI:82812)
diltiazem (CHEBI:101278) is enantiomer of ent-diltiazem (CHEBI:82813)
Incoming diltiazem(1+) (CHEBI:82812) is conjugate acid of diltiazem (CHEBI:101278)
ent-diltiazem (CHEBI:82813) is enantiomer of diltiazem (CHEBI:101278)
IUPAC Name
(2S,3S)-5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate
INNs Sources
diltiazem WHO MedNet
diltiazem WHO MedNet
diltiazem ChemIDplus
diltiazemum ChemIDplus
Synonyms Sources
(+)-cis-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate ester ChEBI
(2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate ChEMBL
(2S-cis)-3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one ChEBI
Acetic acid (2S,3S)-5-(2-dimethylamino-ethyl)-2-(4-methoxy-phenyl)-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-yl ester ChEMBL
D-cis-diltiazem ChEBI
d-cis-diltiazem ChEBI
Database Links Databases
897 DrugCentral
C06958 KEGG COMPOUND
D07845 KEGG DRUG
DB00343 DrugBank
DE1805714 Patent
DE3415035 Patent
Diltiazem Wikipedia
HMDB0014487 HMDB
LSM-2523 LINCS
US3562257 Patent
US4552695 Patent
View more database links
Registry Numbers Types Sources
3573079 Beilstein Registry Number Beilstein
3573079 Reaxys Registry Number Reaxys
42399-41-7 CAS Registry Number KEGG COMPOUND
42399-41-7 CAS Registry Number ChemIDplus
42399-41-7 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations Types Sources
11937779 PubMed citation Europe PMC
16651034 PubMed citation Europe PMC
19167257 PubMed citation Europe PMC
23687551 PubMed citation Europe PMC
24261918 PubMed citation Europe PMC
25122162 PubMed citation Europe PMC
8369596 PubMed citation Europe PMC
Last Modified
22 February 2017