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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:
antihypertensive agent  Any drug used in the treatment of acute or chronic vascular hypertension regardless of pharmacological mechanism.
vasodilator agent  A drug used to cause dilation of the blood vessels.
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