Nimodipine
Title: Nimodipine
CAS Registry Number: 66085-59-4
CAS Name: 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid 2-methoxyethyl 1-methylethyl ester
Additional Names: 2-methoxyethyl 1,4-dihydro-5-(isopropoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate; isopropyl 2-methoxyethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate; 2,6-dimethyl-4-(3¢-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-b-methoxyethyl ester 5-isopropyl ester
Manufacturers' Codes: Bay e 9736
Trademarks: Admon (Esteve); Nimotop (Bayer); Periplum (Italfarmaco)
Molecular Formula: C21H26N2O7
Molecular Weight: 418.44
Percent Composition: C 60.28%, H 6.26%, N 6.69%, O 26.77%
Literature References: Dihydropyridine calcium channel blocker. Prepn: H. Meyer et al., DE 2117571; eidem, US 3799934 (1972, 1974 to Bayer). Pharmacology: R. Towart, S. Kazda, Br. J. Pharmacol. 67, 409P (1979); K. Tanaka et al., Arzneim.-Forsch. 30, 1494 (1980); L. M. Auer, ibid. 31, 1423 (1981). Prepn of isomers and pharmacological comparison with racemate: R. Towart et al., ibid. 32, 338 (1982). Use as cerebral vasodilator: H. Meyer et al., GB 2018134; eidem, US 4406906 (1979, 1983 to Bayer). Effect on associative learning in aging rabbits: R. A. Deyo et al., Science 243, 809 (1989). GC and LC determns in biological fluids: G. J. Krol et al., J. Chromatogr. 305, 105 (1984). Clinical trial in prophylaxis of cerebral vasospasm: G. S. Allen et al., N. Engl. J. Med. 308, 619 (1983). Toxicology: H. Schlüter, Arzneim.-Forsch. 36, 1733 (1986). Series of articles on clinical pharmacology and therapeutic use: Am. J. Cardiol. 55(3), 139B-153B (1985).
Properties: Crystals from petr ether/acetic ester, mp 125°. LD50 in mice, rats (mg/kg): 3562, 6599 orally; 33, 16 i.v. (Schlüter).
Melting point: mp 125°
Toxicity data: LD50 in mice, rats (mg/kg): 3562, 6599 orally; 33, 16 i.v. (Schlüter)
 
Derivative Type: (+)-Form
Properties: [a]D20 +7.9° (c = 0.439 in dioxane).
Optical Rotation: [a]D20 +7.9° (c = 0.439 in dioxane)
 
Derivative Type: (-)-Form
Properties: [a]D20 -7.93° (c = 0.374 in dioxane).
Optical Rotation: [a]D20 -7.93° (c = 0.374 in dioxane)
 
Therap-Cat: Vasodilator (cerebral).
Keywords: Calcium Channel Blocker; Dihydropyridine Derivatives; Vasodilator (Cerebral).

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