1601. Cabergoline

Nomenclature

CAS number: 81409-90-7
(8β)-N-[3-(Dimethylamino)propyl]-N-[(ethylamino)carbonyl]-6-(2-propenyl)ergoline-8-carboxamide; 1-ethyl-3-(3′-dimethylaminopropyl)-3-(6′-allylergoline-8′β-carbonyl)urea; 1-[(6-allylergoline-8β-yl)carbonyl]-1-[3-(dimethylamino)propyl]-3-ethylurea; FCE-21336; Dostinex (Pharmacia & Upjohn).
C26H37N5O2; mol wt 451.60.
C 69.15%, H 8.26%, N 15.51%, O 7.09%.

Description and references

Dopamine D2-receptor agonist. Prepn: P. Salvati et al., BE 888243; eidem, US 4526892 (1981, 1985 both to Farmitalia Carlo Erba). Prepn and bioactivity: E. Brambilla et al., Eur. J. Med. Chem. 24, 421 (1989). Clinical pharmacology: C. Ferrari et al., J. Clin. Endocrinol. Metab. 63, 941 (1986). Veterinary trial as abortifacient in dogs: K. Post et al., Theriogenology 29, 1233 (1988). Clinical evaluation to prevent puerperal lactation: G. B. Melis et al., Obstet. Gynecol. 71, 311 (1988); in hyperprolactinemic disorders: C. Ferrari et al., J. Clin. Endocrinol. Metab. 68, 1201 (1989). Clinical trial in Parkinson's disease: J. T. Hutton et al., Neurology 46, 1062 (1996).

Chemical structure

Properties

White crystals from diethyl ether, mp 102-104°. Sol in ethyl alcohol, chloroform, DMF; slightly sol in 0.1 N HCl; very slightly sol in n-hexane. Insol in water. LD50 orally in male mice: >400 mg/kg (Brambilla).

Derivative

Diphosphate.

Nomenclature

CAS number: 85329-89-1
C26H37N5O2.2H3PO4; mol wt 647.59.
C 48.22%, H 6.69%, N 10.81%, O 24.71%, P 9.57%.

Properties

mp 153-155°.

Therapeutic Category

Prolactin inhibitor; antiparkinsonian.

Therapeutic Category (Veterinary)

Prolactin inhibitor.

Keywords

Antiparkinsonian; Dopamine Receptor Agonist; Prolactin Inhibitor