5937. Metergoline
Nomenclature
CAS number: 17692-51-2
[[(8β)-1,6-Dimethylergolin-8-yl]methyl]carbamic acid phenylmethyl
ester; d-8β-[(carbobenzoxyamino)methyl]-1,6-dimethyl-10α-ergoline; d-N-carbobenzoxydihydro-1-methyllysergamine
I; d-8β-[(carboxyamino)methyl]-1,6-dimethylergoline I
benzyl ester; d-N-carboxydihydro-1-methyllysergamine
I benzyl ester; d-[(4,6,6a,7,8,9,10,10a-octahydro-4,7-dimethyl-10aα-indolo[4,3-fg]quinolin-9β-yl)methyl]carbamic acid benzyl ester; methergoline; Liserdol (Farmitalia); Contralac (Virbac). C25H29N3O2; mol wt 403.52.
C 74.41%, H 7.24%, N 10.41%, O 7.93%.
Description and references
Serotonin 5HT-receptor antagonist. Prepn: Bernardi et al., Gazz. Chim. Ital. 94, 936 (1964); Camerino et al., US 3238211 (1966 to Farmitalia). Pharmacology: C. Beretta et al., Nature 207, 421 (1965). Metabolic studies: Arcamone et al., Boll. Chim. Farm. 110, 704 (1971). Mode of action study: L. Krulich et al., Endocrinology 108, 1115 (1981). Clinical antiprolactin activity: F. Scapin et al., Eur. J. Clin. Pharmacol. 22, 181 (1982); A. Caballero et al., J. Reprod. Med. 32, 115 (1987).
Properties
Crystals from benzene + ether, mp 146-149°. [α]D28 7 ±2°. uv max: 291 nm (E1%1cm 165). Very sol in pyridine; sol in alc, acetone, chloroform. Practically insol in benzene, ether, water. LD50 in mice (mg/kg): 85 i.p., 430 orally; in rats (mg/kg): >800 orally (Beretta).Therapeutic Category
Prolactin inhibitor.
Therapeutic Category (Veterinary)
Prolactin inhibitor.Keywords
Prolactin Inhibitor