5240. Isradipine

Nomenclature

CAS number: 75695-93-1
4-(4-Benzofurazanyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylic acid methyl 1-methylethyl ester; isopropyl 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-3-pyridinecarboxylate; 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydro-3-isopropyloxycarbonylpyridine-5-carboxylic acid methyl ester; isrodipine; PN-200-110; Clivoten (Lifepharma); DynaCirc (Novartis); Esradin (Sigma-Tau); Lomir (Novartis); Prescal (Novartis).
C19H21N3O5; mol wt 371.39.
C 61.45%, H 5.70%, N 11.31%, O 21.54%.

Description and references

Dihydropyridine calcium channel blocker. Prepn: P. Neumann, DE 2949491; idem, US 4466972 (1980, 1984 both to Sandoz). Prepn of enantiomers: A. Vogel, DE 3320616 (1983 to Sandoz), C.A. 101, 7162s (1984). Comparative study of in vitro effects on human and canine cerebral arteries: E. Müller-Schweinitzer, P. Neumann, J. Cereb. Blood Flow Metab. 3, 354 (1983). Effect on α-adrenoceptor mediated vasoconstriction in rats: K. Jie et al., Arch. Int. Pharmacodyn. 278, 72 (1985). Pharmacokinetics: F. L. S. Tee, J. M. Jaffe, Eur. J. Clin. Pharmacol. 32, 361 (1987). Clinical evaluation in angina and coronary artery disease: C. E. Handler, E. Sowton, ibid. 27, 415 (1984); in hypertension: E. B. Nelson et al., Clin. Pharmacol. Ther. 40, 694 (1986). Comparison of hemodynamic effects of enantiomers: R. P. Hof et al., J. Cardiovasc. Pharmacol. 8, 221 (1986). Series of articles on pharmacology and clinical use: Am. J. Med. 86, 1-146 (1989).

Chemical structure

Properties

mp 168-170°.

Derivative

S(+)-Form.

Nomenclature

PN-205-033.

Properties

Crystals from ether + hexane, mp 142°. [α]D20 +6.7° (c = 1.5 in ethanol).

Derivative

R()-Form.

Nomenclature

PN-205-034.

Properties

Crystals from ether + hexane, mp 140°. [α]D20 6.7° (c = 1.67 in ethanol).

Therapeutic Category

Antihypertensive; antianginal.

Keywords

Antianginal; Antihypertensive; Dihydropyridine Derivatives; Calcium Channel Blocker; Dihydropyridine Derivatives