Isradipine

4 - (4 - benzofurazanyl ) -1, 4- dihydro- 2,6-dimethyl- 3 ,5- pyridindicarboxylsäure, methyl 1- methylethyl ester IUPAC

C08CA02

Antihypertensive

Calcium antagonist

168-170 ° C ( racemate)

• S ( ) 142 ° C
• R (-) 140 ° C

Template: Infobox chemical / molecular formula search available

Isradipine is a drug from the class of calcium antagonists of the dihydropyridine type, which is used as antihypertensive agent. As a special structure feature, it has a benzo - oxadiazole ring (deprecated benzo furazan ) on.

Isradipine is well absorbed from the gut, but undergoes extensive first - pass metabolism, the bioavailability is given as 15-24 %. After 0.4 to 2.5 h, a maximum plasma concentration is reached; the half-life is about 9 h, the enzyme cytochrome P450 3A4 is involved in the degradation.

Preparation and Properties

Isradipine is obtained after Heitzmann from 2,1,3- benzoxadiazol by reaction with LDA in dimethylformamide and heating the resulting 2,1,3- benzoxadiazol - aldehyde with aminocrotonate and acetoacetate in isopropanol in good yield. The crystalline yellow substance consists of a mixture of (S) - ( ) - and (R ) - (- )-form, melts at 168 to 170 ° C and decomposes to light and exposure to air, and when heated. Therefore, it is stored in the dark at 2-8 ° C under nitrogen atmosphere.

Effects, absorption and elimination

The nifedipine -like calcium antagonist with high affinity for calcium channels in arterial smooth muscle vascular causes a very selective Tonussenkung vascular smooth muscle. Studies have shown that the substance in addition to the vasodilatory also has a natriuretic ( sodium- excreting ) effect and left ventricular hypertrophy regresses during isradipine therapy. For oral administration, the drug is absorbed in the intestine and to 90-95% to 97% bound to plasma proteins. In animal experiments, isradipine was able to penetrate the blood- brain barrier. When used in human medicine, the fabric is completely metabolized and excreted 60-65 % through the kidneys and to 25-30% in the faeces.

Trade names

Lomir (A, CH), Vascal (D)