33286-22-5 Usage
Biological Activity
Antihypertensive and cardioprotective agent; an inhibitor of L-type Ca 2+ channels.
Uses
Diltiazem Hydrochloride is a calcium channel blocker with vasodilating activity. Anti-anginal; anti-hypertensive; anti-arrhythmic (class IV).
Manufacturing Process
β-Diethylaminoethyl chloride is condensed with 2-(4-methoxyphenyl)-3-
hydroxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one in a first step. Then a
mixture of 1.5 grams of 2-(4-methoxyphenyl)-3-hydroxy-5-(βdimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one and 20 ml of
acetic anhydride was heated on a water bath for 5 hours. The reaction
mixture was evaporated under reduced pressure to remove acetic anhydride
and the concentrated product was poured into ice water. The resulting mixture
was made alkaline with sodium bicarbonate and extracted with chloroform.
The chloroform layer was dried and evaporated to remove the solvent. The
residue was dissolved in acetone, and an ethanol solution containing hydrogen
chloride was added thereto producing 1.53 grams of 2-(4-methoxyphenyl)3-
acetoxy-5-(β-dimethylaminoethyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
hydrochloride having a melting point from 187° to 188°C.The starting material is made by reacting 4-methoxybenzaldehyde with ethyl
chloroacetate; that product with sodium ethoxide; and that product with 2-
aminothiophenol.
Originator
Herbesser,TANABE SEIYAKU,Japan,1974
Uses
Peripheral Vasodilator
Uses
A calcium channel blocher with vasodilating activity. Antianginal; antihypertensive; antiarrhythmic (class IV).
Chemical Properties
Fine Needles
General Description
Diltiazem hydrochloride,(+)-cis-3-(acetoxy)-5-[2(dimethylamino)ethyl]-2,3-dihydro-2-(4-methoxyphenyl)1,5-benzothiazepin-4(5H)one hydrochloride(Cardizem), was developed and introduced inJapan as a cardiovascular agent to treat angina pectoris. Itwas observed to dilate peripheral arteries and arterioles. Thedrug increases myocardial oxygen supply by relieving coronaryartery spasm and reduces myocardial oxygen demandby decreasing heart rate and reducing overload. Diltiazemhydrochloride is used in patients with variant angina. Thedrug has electrophysiological properties similar to those ofverapamil and is used in clinically similar treatment conditionsas an antiarrhythmic agent, but it is less potent.The drug is absorbed rapidly and almost completely fromthe digestive tract. It reaches peak plasma levels within 1hour after administration in gelatin capsules. Oral formulationson the market are sustained-release preparations providingpeak plasma levels 3 to 4 hours after administration.
Uses
An antianginal, antihypertensive. Regulates Calcium release from intracellular stores in neutrophils
Brand name
Cardizem (Biovail); Cartia (Andrx); Dilacor (Watson); Diltzac (Apotex); Taztia (Andrx); Tiazac (Biovail).
Definition
ChEBI: A hydrochloride salt resulting from the reaction of equimolar amounts of diltiazem and hydrogen chloride. A calcium-channel blocker and vasodilator, it is used in the management of angina pectoris and hypertension.
Therapeutic Function
Coronary vasodilator
Uses
antihypertensive, sedative, antibacterial
InChI:InChI=1/C22H26N2O4S.ClH/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;1H/t20-,21+;/m1./s1