Classification Term: 420

Benzothiazepines (ontology term: CHEMONTID:0000317)

Organic compounds containing a benzene fused to a thiazepine ring (a seven-membered ring with a nitrogen atom and a sulfur atom replacing two carbon atoms)." []

found 11 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Organoheterocyclic compounds

Child Taxonomies: Dibenzothiazepines

Diltiazem

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

C22H26N2O4S (414.16131960000007)

Diltiazem is only found in individuals that have used or taken this drug. It is a benzothiazepine derivative with vasodilating action due to its antagonism of the actions of the calcium ion in membrane functions. It is also teratogenic. [PubChem]Possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, diltiazem, like verapamil, inhibits the influx of extracellular calcium across both the myocardial and vascular smooth muscle cell membranes. The resultant inhibition of the contractile processes of the myocardial smooth muscle cells leads to dilation of the coronary and systemic arteries and improved oxygen delivery to the myocardial tissue. C - Cardiovascular system > C08 - Calcium channel blockers > C08D - Selective calcium channel blockers with direct cardiac effects > C08DB - Benzothiazepine derivatives C - Cardiovascular system > C05 - Vasoprotectives > C05A - Agents for treatment of hemorrhoids and anal fissures for topical use > C05AE - Muscle relaxants C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent > C333 - Calcium Channel Blocker D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D000077264 - Calcium-Regulating Hormones and Agents D049990 - Membrane Transport Modulators C93038 - Cation Channel Blocker

Deacetyldiltiazem

(2S,3S)-5-[2-(dimethylamino)ethyl]-3-hydroxy-2-(4-methoxyphenyl)-2,3,4,5-tetrahydro-1,5-benzothiazepin-4-one

C20H24N2O3S (372.1507554)

Deacetyldiltiazem is a metabolite product of the drug Diltiazem (a coronary vasodilator), and is present in the plasma of individuals taking that medication. (PMID 2328299). The action mechanisms involved in the effect of Deacetyldiltiazem on blood rheological (erythrocyte deformation) properties appeared to be similar to Diltiazem, but different from other metabolites of this drug. (PMID 3411434). Deacetyldiltiazem is a metabolite product of the drug Diltiazem (a coronary vasodilator), and is present in the plasma of individuals taking that medication. (PMID 2328299)

N-Desmethyldiltiazem

(3S)-2-(4-methoxyphenyl)-5-[2-(methylamino)ethyl]-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate

C21H24N2O4S (400.14567040000003)

N-Desmethyldiltiazem is a metabolite of diltiazem. Diltiazem is a nondihydropyridine (non-DHP) member of the class of drugs known as calcium channel blockers, used in the treatment of hypertension, angina pectoris, and some types of arrhythmia. It is also an effective preventive medication for migraine. It is a class 3 antianginal drug, and a class IV antiarrhythmic. It is a common adulterant of cocaine seized in the UK, and has been found to reduce cocaine cravings in rats, indicating it may prolong the high. (Wikipedia)

1,5-Benzothiazepine

C9H7NS (161.0299182)

Dilacor XR

5-[2-(dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate

C22H26N2O4S (414.16131960000007)

D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents D000077264 - Calcium-Regulating Hormones and Agents D049990 - Membrane Transport Modulators

8-Chlorodiltiazem

3-Acetoxy-8-chloro-5-(2-(dimethylamino)ethyl)-2,3-dihydro-2-(4-methoxyphenyl)-1,5-benzothiazepin-4-(5H)-one maleate

C22H25ClN2O4S (448.12234800000004)

D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors D002317 - Cardiovascular Agents > D002121 - Calcium Channel Blockers D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D000077264 - Calcium-Regulating Hormones and Agents D049990 - Membrane Transport Modulators

1,5-Benzothiazepin-4(5H)-one, 2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-5-(2-(methylamino)ethyl)-, (2S,3S)-

C19H22N2O3S (358.1351062)

(3R,5R)-3-Butyl-3-ethyl-5-phenyl-4,5-dihydro-2H-1$l^{6},4-benzothiazepine 1,1-dioxide

C21H27NO2S (357.17624020000005)

Pentanedioic acid, 3-((((3R,5R)-3-butyl-3-ethyl-2,3,4,5-tetrahydro-7-methoxy-1,1-dioxido-5-phenyl-1,4-benzothiazepin-8-yl)methyl)amino)-

C28H38N2O7S (546.2399598)

O-Desmethyldiltiazem

5-[2-(Dimethylamino)ethyl]-2-(4-hydroxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetic acid

C21H24N2O4S (400.14567040000003)

3-Acetoxy-5-(2-(dimethylamino)ethyl)-2,3-dihydro-8-methyl-2-(4-methylphenyl)-1,5-benzothiazepin-4(5H)-one

5-[2-(Dimethylamino)ethyl]-8-methyl-2-(4-methylphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetic acid

C23H28N2O3S (412.18205380000006)