1416. Bromocriptine

Nomenclature

CAS number: 25614-03-3
(5′α)-2-Bromo-12′-hydroxy-2′-(1-methylethyl)-5′-(2-methylpropyl)ergotaman-3′,6′,18-trione; 2-bromoergocryptine; 2-bromo-α-ergokryptin; CB-154.
C32H40BrN5O5; mol wt 654.59.
C 58.71%, H 6.16%, Br 12.21%, N 10.70%, O 12.22%.

Description and references

Dopamine D2 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). LC/MS/MS determn in plasma: A. Salvador et al., J. Chromatogr. B 820, 237 (2005). 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). Clinical study in type 2 diabetes: H. Pijl et al., ibid. 23, 1154 (2000). Effects of prolactin concentration and estrus in beagles: N. J. Beijerink et al., Theriogenology 60, 1379 (2003). Comprehensive description: D. A. Giron-Forest, W. D. Schnleber, 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); of clinical experience in rheumatic and autoimmune diseases: R. W. McMurray, Semin. Arthritis Rheum. 31, 21-32 (2001).

Chemical structure

Properties

Crystals from methyl ethyl ketone-isopropyl ether, mp 215-218° (dec). [α]D20 195° (c = 1 in methylene chloride).

Derivative

Methanesulfonate.

Nomenclature

CAS number: 22260-51-1
CB-154 mesylate; Bromo-Kin (Sanofi-Aventis); Cycloset (VeroScience); Parlodel (Novartis); Pravidel (Novartis).
C32H40BrN5O5.CH3SO3H; mol wt 750.70.
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). [α]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).

Therapeutic Category

Prolactin inhibitor; antiparkinsonian; antidiabetic.

Therapeutic Category (Veterinary)

Prolactin inhibitor.

Keywords

Antiparkinsonian; Dopamine Receptor Agonist; Prolactin Inhibitor; Antidiabetic