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Diltiazem

Diltiazem Structure
CAS No.
42399-41-7
Chemical Name:
Diltiazem
Synonyms
DILTIAZEN;Dilthiazem;(2S,3S)-5-(2-(diMethylaMino)ethyl)-2-(4-Methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate;Coras;NSC7324;NSC 7324;NSC-7324;DILTIAZEM;Adizem XL;d-Diltiazem
CBNumber:
CB5715839
Molecular Formula:
C22H26N2O4S
Molecular Weight:
414.52
MOL File:
42399-41-7.mol
MSDS File:
SDS
Modify Date:
2024/6/19 22:55:17

Diltiazem Properties

Melting point 212 °C (decomp)
Boiling point 594.4±50.0 °C(Predicted)
Density 1.26±0.1 g/cm3(Predicted)
storage temp. -20°C Freezer
solubility Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka pKa 7.70 (Uncertain)
form Solid
color White to Off-White
CAS DataBase Reference 42399-41-7(CAS DataBase Reference)
NIST Chemistry Reference Diltiazem(42399-41-7)
EPA Substance Registry System 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S,3S)- (42399-41-7)

Diltiazem Chemical Properties,Uses,Production

Uses

Diltiazem is a potent vasodilator compound. Antihypertensive.

Definition

ChEBI: 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 m nagement of angina pectoris and hypertension.

Mechanism of action

Diltiazem reduces the transmembrane influx of calcium ions into cells of cardiac muscle and smooth musculature of vessels. It causes dilation of coronary and peripheral vessels, increases coronary blood flow, and prevents development of coronary artery spasms. It lowers elevated arterial pressure and reduces tachycardia.

Clinical Use

The antiarrhythmic actions and uses of diltiazem are similar to those of verapamil. Diltiazem is effective in controlling the ventricular rate in patients with atrial flutter or atrial fibrillation.

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(+)-5-[2-(Dimethylamino)ethyl]-cis-2,3-dihydro-3-hydroxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one acetate (ester) (2s-cis)-dro-2-(4-methoxyphenyl) (2S,3S)-2,3-Dihydro-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-1,5-benzothiazepine-4(5H)-one acetate (2R)-3α-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [2R,(+)]-3α-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 3α-(Acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 3α-Acetyloxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2α-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [(2S,3S)-5-(2-dimethylaminoethyl)-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] acetate [(2S,3S)-5-(2-dimethylaminoethyl)-2-(4-methoxyphenyl)-4-oxo-2,3-dihydro-1,5-benzothiazepin-3-yl] ethanoate acetic acid [(2S,3S)-5-(2-dimethylaminoethyl)-4-keto-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-3-yl] ester Diltiazem (free base) O-DesMethyl DiltiazeM, HydrobroMide (Cis - RaceMic) 1,5-benzothiazepin-4(5h)-one,3-(acetyloxy)-5-(2-(dimethylamino)ethyl)-2,3-dihy 1,5-benzothiazepin-4(5h)-one,3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihy 5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate d-cis-diltiazem (+)-CIS-DILTIAZEM DILTIAZEM (2S)-5-[2-(Dimethylamino)ethyl]-2α,3α-dihydro-3β-acetyloxy-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one [(3S,4S)-6-(2-dimethylaminoethyl)-3-(4-methoxyphenyl)-5-oxo-2-thia-6-azabicyclo[5.4.0]undeca-7,9,11-trien-4-yl] acetate 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-2-(dimethylamino)ethyl-2,3-dihydro-2-(4-methoxyphenyl)-, (2S,3S)- 1,5-Benzothiazepin-4(5H)-one, 3-(acetyloxy)-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)-, (2S-cis)- Adizem XL Coras d-Diltiazem TILDIEM300LP Diltiazem (base and/or unspecified salts) 3-amino-1,2,4-triazole-1-carboxylic acid ethyl ester high quality Diltiazem High purity diltiazem/diltiazem hydrochloride Diltiazem HCl salt Diltiazem USP/EP/BP NSC 7324 NSC7324 NSC-7324 (2S,3S)-5-(2-(diMethylaMino)ethyl)-2-(4-Methoxyphenyl)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-yl acetate DILTIAZEN Dilthiazem (2S-Cis)-3-(Acetyloxy)-5-[2-dimethylamino)ethyl]-2,3-dihydro-2-(4methoxy phenyl)- 1,5benzothiazepin-4(5H)-one D Diltiazem HCl (2S,3S)-5-[2-(Dimethylamino)ethyl]-2-(4-methoxyphenyl)-4-oxo- 2,3,4,5-tetrahydro-1,5-benzothiazepin-3-yl acetate hydrochloride Diltiazem fandachem 42399-41-7 43299-41-7 C22H26N2O4S 42399-41-7