5474. LH-RH

Nomenclature

CAS number: 9034-40-6
Luteinizing hormone-releasing factor; LH-RF; luteinizing hormone-releasing hormone; LRF; LRH; gonadorelin; gonadotropin-releasing factor; gonadoliberin; luliberin; LH-RH/FSH-RH; Fertagyl (Intervet); Fertiral (HMR); Kryptocur (HMR); Relefact LH-RH (HMR).
C55H75N17O13; mol wt 1182.29.
C 55.87%, H 6.39%, N 20.14%, O 17.59%.

Description and references

Neurohumoral hormone produced in the hypothalamus which stimulates the secretion of the pituitary hormones, LH (luteinizing hormone) and FSH (follicle-stimulating hormone) q.q.v., which in turn produce changes resulting in the induction of ovulation. Isoln from porcine hypothalamic extracts: A. V. Schally et al., Biochem. Biophys. Res. Commun. 43, 393 (1971). Structure: Matsuo et al., ibid. 1334; Baba et al., ibid. 44, 459 (1971); Burgus et al., C. R. Seances Acad. Sci. Ser. D 273, 1611 (1971). Solid phase synthesis: Monahan et al., ibid. 508; Monahan, Rivier, Biochem. Biophys. Res. Commun. 48, 1100 (1972); Coy et al., Methods Enzymol. 37, 416 (1975); D. H. Rich, S. K. Gurwara, Tetrahedron Lett. 1975, 301. Industrial prepn: Geiger et al., DE 2213737 (1973 to Hoechst). Confirmation of biological activity: A. V. Schally et al., Science 173, 1036 (1971). Pharmacokinetics: T. W. Redding, J. Clin. Endocrinol. Metab. 37, 626 (1973). Reviews of physiology and implications in fertility control: A. V. Schally et al., Fertil. Steril. 22, 703 (1971); R. Guillemin, Contraception 6, 1 (1972). Review of LH-RH and other hypothalamic hormones: A. V. Schally et al., Science 179, 341 (1973); A. V. Schally, ibid. 202, 18-28 (1978); of LH-RH and somatostatin, q.v.: S. M. McCann, Annu. Rev. Pharmacol. Toxicol. 22, 491-515 (1982). General reviews: J. Sandow, Clin. Endocrinol. 18, 571-592 (1983); S. M. McCann, J. Endocrinol. Invest. 6, 243-251 (1983).

Chemical structure

Properties

[α]D25 50° (1% acetic acid). Chymotrypsin, papain, subtilisin, thermolysin destroy the pituitary hormone releasing action of LH-RH.

Derivative

Acetate (salt) hydrate.

Nomenclature

Gonadorelin acetate; Cystorelin (Abbott); Hypocrine (Tanabe Seiyaku); Lutrelef (Ferring); Lutrepulse (Ortho).

Description and references

C55H75N17O13.xC2H4O2.yH2O, as the diacetate tetrahydrate or a mixture of monoacetate and diacetate hydrates.

Derivative

Hydrochloride.

Nomenclature

CAS number: 51952-41-1
AY-24031; HRF (Ayerst); Factrel (Ayerst).

Therapeutic Category

Gonad-stimulating principle.

Therapeutic Category (Veterinary)

Gonad-stimulating principle.

Keywords

Gonad-Stimulating Principle