Title: Bromocriptine
CAS Registry Number: 25614-03-3
CAS Name: (5¢a)-2-Bromo-12¢-hydroxy-2¢-(1-methylethyl)-5¢-(2-methylpropyl)ergotaman-3¢,6¢,18-trione
Additional Names: 2-bromoergocryptine; 2-bromo-a-ergokryptin
Manufacturers' Codes: CB-154
Molecular Formula: C32H40BrN5O5
Molecular Weight: 654.59
Percent Composition: C 58.71%, H 6.16%, Br 12.21%, N 10.70%, O 12.22%
Literature References: Dopamine receptor agonist; derivative of the ergotoxin group of ergot alkaloids. Prepn: E. Flückiger et al., DE 1926045; eidem, US 3752814 (1969, 1973 both to Sandoz). Pharmacology: E. Flückiger, H. R. Wagner, Experientia 24, 1130 (1968); E. Del Pozo et al., Schweiz. Med. Wochenschr. 103, 847 (1973). Relationship of stereochemistry and biological activity: H. P. Weber, Adv. Biochem. Psychopharmacol. 23, 25 (1980); N. Camerman, A. Camerman, Mol. Pharmacol. 19, 517 (1981). Long term clinical trial in Parkinson's disease: T. Nakanishi et al., Eur. Neurol. 32, Suppl. 1, 9 (1992). Clinical effect on body weight and glucose tolerance in obesity: A. H. Cincotta, A. H. Meier, Diabetes Care 19, 667 (1996). Comprehensive description: D. A. Giron-Forest, W. D. Schönleber, Anal. Profiles Drug Subs. 8, 47-81 (1979). Review of pharmacology, toxicology and therapeutic uses: D. Parkes, Adv. Drug Res. 12, 247-344 (1977); of therapeutic applications in endocrine and neurological diseases: K. Y. Ho, M. O. Thorner, Drugs 36, 67-82 (1988).
Properties: Crystals from methyl ethyl ketone-isopropyl ether, mp 215-218° (dec). [a]D20 -195° (c = 1 in methylene chloride).
Melting point: mp 215-218° (dec)
Optical Rotation: [a]D20 -195° (c = 1 in methylene chloride)
Derivative Type: Methanesulfonate
CAS Registry Number: 22260-51-1
Manufacturers' Codes: CB-154 mesylate
Trademarks: Parlodel (Novartis); Pravidel (Novartis)
Molecular Formula: C32H40BrN5O5.CH3SO3H
Molecular Weight: 750.70
Percent Composition: C 52.80%, H 5.91%, Br 10.64%, N 9.33%, O 17.05%, S 4.27%
Properties: Crystals from methyl ethyl ketone, mp 192-196° (dec). [a]D20 +95° (c = 1 in methanol-methylene chloride). Soly at 25° (mg/ml): methanol 910; ethanol 23.0; water 0.8; chloroform 0.45; benzene <0.1; hexane <0.1. pKa 4.90. LD50 in mice, rats, rabbits (mg/kg): 190, 72, 12.5 i.v. (Parkes).
Melting point: mp 192-196° (dec)
pKa: pKa 4.90
Optical Rotation: [a]D20 +95° (c = 1 in methanol-methylene chloride)
Toxicity data: LD50 in mice, rats, rabbits (mg/kg): 190, 72, 12.5 i.v. (Parkes)
Therap-Cat: Prolactin inhibitor; antiparkinsonian.
Keywords: Antiparkinsonian; Dopamine Receptor Agonist; Prolactin Inhibitor. |