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diltiazem
The (S,S)-diastereoisomer of 2,3-dihydro-1,5-benzothiazepin-4(5H)-one in which positions 2 and 3 are substituted by 4-methoxyphenyl and acetoxy, respectively, while the hydrogen attached to the nitrogen is substituted by a 2-(dimethylamino)ethyl group. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.


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03. Biological Effects of Specific Chemicals: biophysical uses [CHEBI:52208] > membrane transport modulator [CHEBI:38632] > calcium channel modulator [CHEBI:38808] > calcium channel blocker [CHEBI:38215]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biophysical uses [CHEBI:52208] (136) 
 membrane transport modulator [CHEBI:38632] (122) 
 calcium channel modulator [CHEBI:38808] (32) 
 calcium channel blocker [CHEBI:38215] (24) 
 diltiazem [CHEBI:101278] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antihypertensive agent [CHEBI:35674] (104) 
 diltiazem [CHEBI:101278] (1)
 cardiovascular drug [CHEBI:35554] (162) 
 vasodilator agent [CHEBI:35620] (65) 
 diltiazem [CHEBI:101278] (1)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 p-block molecular entity [CHEBI:33675] (25343) 
 pnictogen molecular entity [CHEBI:33302] (10027) 
 nitrogen molecular entity [CHEBI:51143] (7930) 
 organonitrogen compound [CHEBI:35352] (6705) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 chalcogen molecular entity [CHEBI:33304] (15225) 
 sulfur molecular entity [CHEBI:26835] (1541) 
 organosulfur compound [CHEBI:33261] (1005) 
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organosulfur compound [CHEBI:33261] (1005) 
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organonitrogen compound [CHEBI:35352] (6705) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organosulfur compound [CHEBI:33261] (1005) 
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 polycyclic compound [CHEBI:33635] (4078) 
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 bicyclic compound [CHEBI:33636] (1511) 
 heterobicyclic compound [CHEBI:33672] (1315) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 heterobicyclic compound [CHEBI:33672] (1315) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 organonitrogen heterocyclic compound [CHEBI:38101] (3202) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organosulfur heterocyclic compound [CHEBI:38106] (367) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterobicyclic compound [CHEBI:27171] (1315) 
 benzothiazepine [CHEBI:48684] (1) 
 diltiazem [CHEBI:101278] (1)
ChEBI Compound Accession Identifier  [CHEBI:101278]
ChEBI Compound Description  The (S,S)-diastereoisomer of 2,3-dihydro-1,5-benzothiazepin-4(5H)-one in which positions 2 and 3 are substituted by 4-methoxyphenyl and acetoxy, respectively, while the hydrogen attached to the nitrogen is substituted by a 2-(dimethylamino)ethyl group. A calcium-channel blocker and vasodilator, it is used as the hydrochloride in the management of angina pectoris and hypertension.
ChEBI Compound Identification Number  101278
ChEBI InChI Value  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
ChEBI InChIKey Value  HSUGRBWQSSZJOP-RTWAWAEBSA-N
ChEBI Compound Name  diltiazem
ChEBI SMILES Value  COc1ccc(cc1)[C@@H]1Sc2ccccc2N(CCN(C)C)C(=O)[C@@H]1OC(C)=O
ChEBI Substance ID  85306411
ChEBI URL  ChEBI:101278
ChemSpider ID  35850
Ontomatica Chemical Accession Key (OnChAKey)  HSUGRBWQSSZJOP_RTWAWAEBSA_N_000_000000
PubChem Compound ID  39186