5457. Leuprolide

Nomenclature

CAS number: 53714-56-0
6-d-Leucine-9-(N-ethyl-l-prolinamide)-10-deglycinamideluteinizing hormone-releasing factor (pig); leuprorelin; (d-Leu6)-des-Gly10-LH-RH-ethylamide.
C59H84N16O12; mol wt 1209.40.
C 58.59%, H 7.00%, N 18.53%, O 15.88%.

Description and references

Synthetic nonapeptide agonist analog of LH-RH, q.v. Prepn: M. Fujino et al., DE 2446005 (1975 to Takeda), C.A. 83, 10895y (1975); R. L. Gendrich et al., US 4005063 (1977 to Abbott). Synthesis: J. A. Vilchez-Martinez et al., Biochem. Biophys. Res. Commun. 59, 1226 (1974); M. Fujino et al., ibid. 60, 406 (1974); E. Nicolás et al., Tetrahedron 53, 3179 (1997). Comparison of biological activity with natural LH-RH: D. H. Coy et al., ibid. 67, 576 (1975). Pharmacokinetics: L. T. Sennello et al., J. Pharm. Sci. 75, 158 (1986). Clinical efficacy in prostatic carcinoma: M. B. Garnick et al., N. Engl. J. Med. 311, 1281 (1984); in benign prostatic hypertrophy: L. M. Eri, K. J. Tveter, J. Urol. 150, 359 (1993). Clinical trial in endometriosis: J. M. Wheeler et al., Am. J. Obstet. Gynecol. 167, 1367 (1992). Review of extended release formulation adjuvant therapy in prostate cancer: R. Perez-Marrero, R. C. Tyler, Expert Opin. Pharmacother. 5, 447-457 (2004).

Chemical structure

Properties

Fluffy solid. [α]D25 31.7° (c = 1 in 1% acetic acid).

Derivative

Monoacetate (salt).

Nomenclature

CAS number: 74381-53-6
Leuprolide acetate; Abbott 43818; A-43818; TAP-144; Carcinil (Abbott); Eligard (Sanofi-Aventis); Enantone (Takeda); Leuplin (Takeda); Lucrin (Abbott); Lupron (TAP); Prostap (Wyeth); Viadur (Alza).
C59H84N16O12.C2H4O2; mol wt 1269.45.
C 57.71%, H 6.99%, N 17.65%, O 17.64%.

Therapeutic Category

Antineoplastic (hormonal); LH-RH agonist.

Therapeutic Category (Veterinary)

LH-RH agonist.

Keywords

Antineoplastic (Hormonal); LH-RH Analogs; LH-RH Agonist