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CHEBI:101278 - diltiazem

Default Structure
ChEBI IDCHEBI:101278
ChEBI Namediltiazem
Stars
DefinitionA 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.
Secondary ChEBI IDCHEBI:4602
Last Modified22 February 2017
DownloadsMolfile
FormulaC22H26N2O4S
Net Charge0
Average Mass414.527
Monoisotopic Mass414.16133
SMILESCOc1ccc([C@@H]2Sc3ccccc3N(CCN(C)C)C(=O)[C@@H]2OC(C)=O)cc1
InChIInChI=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
InChIKeyHSUGRBWQSSZJOP-RTWAWAEBSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
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.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
diltiazemWHO MedNet
diltiazemWHO MedNet
diltiazemChemIDplus
diltiazemumChemIDplus
Synonyms  Source
(2S-cis)-3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-oneChEBI
(2S,3S)-5-(2-(dimethylamino)ethyl)-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetateChEMBL
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 esterChEMBL
(+)-cis-5-[2-(dimethylamino)ethyl]-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate esterChEBI
d-cis-diltiazemChEBI
D-cis-diltiazemChEBI
Manual XrefsDatabases
1863VSDB
897DrugCentral
C06958KEGG COMPOUND
D07845KEGG DRUG
DB00343DrugBank
DE1805714Patent
DE3415035Patent
DiltiazemWikipedia
HMDB0014487HMDB
LSM-2523LINCS
US3562257Patent
US4552695Patent
Registry NumbersSources
Reaxys:3573079Reaxys
CAS:42399-41-7KEGG COMPOUND
CAS:42399-41-7ChemIDplus
CAS:42399-41-7NIST Chemistry WebBook
Citations