9164. Terguride

Nomenclature

CAS number: 37686-84-3
N,N-Diethyl-N′-[(8α)-6-methylergolin-8-yl]urea; N-(d-6-methyl-8-isoergolin-1-yl)-N′,N′-diethylurea; 6-methyl-8α-(diethylcarbamoylamino)ergoline; 9,10α-dihydrolisuride; 9,10-transdihydrolisuride; TDHL.
C20H28N4O; mol wt 340.46.
C 70.56%, H 8.29%, N 16.46%, O 4.70%.

Description and references

Ergot derivative; dihydrogenated analog of lisuride, q.v. Exhibits dopamine agonist and antagonist activity. Prepn: V. Zikán et al., Collect. Czech. Chem. Commun. 37, 2600 (1972); eidem, DE 2238540; eidem, US 3953454 (1973, 1976 both to Spofa). Physical properties: A. Cerny et al., Collect. Czech. Chem. Commun. 52, 1331 (1987). Pharmacology in animals and humans: H. Wachtel, R. Dorow, Life Sci. 32, 421 (1983). Receptor binding studies in rat brain: W. Kehr et al., Acta Pharm. Suec. 1983, Suppl. 2, 98; M. W. Valchár et al., Eur. J. Pharmacol. 136, 97 (1987). Evaluation in animal models of Parkinson's disease: W. C. Koller, G. Herbster, Neurology 37, 723 (1987); T. Brücke et al., Eur. J. Pharmacol. 148, 445 (1988). Radioreceptor assay in biological fluids: R. Lapka et al., J. Pharmacol. Methods 11, 263 (1984). Pharmacokinetics in humans: W. Krause et al., Eur. J. Clin. Pharmacol. 27, 335 (1984). Clinical evaluation in Huntington's disease: S. Bassi et al., Neurology 36, 984 (1986); in Parkinson's disease: T. Brücke et al., Adv. Neurol. 45, 573 (1986); I. Suchy et al., ibid. 577; in hyperprolactinemia and acromegaly: D. Dallabonzana et al., J. Clin. Endocrinol. Metab. 63, 1002 (1986).

Chemical structure

Properties

Crystals from ethanol, mp 203-204° (dec). [α]D20 +30° (c = 1 in pyridine). Also reported as crystals from ethanol, mp 205-207° (dec) (Cerny). [α]D20 +29.0° (c = 0.2 in pyridine). uv max: 292, 281, 224 nm (log ε 3.72, 3.81, 4.42). Practically insol in water.

Derivative

Hydrogen maleate.

Nomenclature

CAS number: 37686-85-4
SH-406; VUFB-6638; ZK-31224; Dironyl (Schering AG); Mysalfon (Spofa).
C20H28N4O.C4H4O4; mol wt 456.53.
C 63.14%, H 7.07%, N 12.27%, O 17.52%.

Properties

Crystals from ethanol, mp 190-191°.

Derivative

Hydrogen maleate hydrate.

Properties

Crystals from ethanol, mp 150-153°. [α]D20 -15.0° (c = 0.1 in H2O). Soly in water: 1.26 mg/ml.

Therapeutic Category

Antiparkinsonian; antihyperprolactinemic.

Keywords

Antiparkinsonian; Prolactin Inhibitor