4365. Ganirelix

Nomenclature

CAS number: 124904-93-4
N-Acetyl-3-(2-naphthalenyl)-d-alanyl-4-chloro-d-phenylalanyl-3-(3-pyridinyl)-d-alanyl-l-seryl-l-tyrosyl-N6-[bis(ethylamino)methylene]-d-lysyl-l-leucyl-N6-[bis(ethylamino)methylene]-l-lysyl-l-prolyl-d-alaninamide; [N-Ac-d-Nal(2)1-d-pCl-Phe2-d-Pal(3)3-d-hArg(Et2)6-hArg(Et2)8-d-Ala10]GnRH.
C80H113ClN18O13; mol wt 1570.32.
C 61.19%, H 7.25%, Cl 2.26%, N 16.06%, O 13.25%.

Description and references

Decapeptide LH-RH antagonist. Prepn and structure-activity studies: J. J. Nestor, Jr. et al. in Peptides 1988: Proc. 20th Eur. Peptide Symp., G. Jung, E. Bayer, Eds. (Walter de Gruyter, Berlin, 1989) pp 592-594; eidem, J. Med. Chem. 35, 3942 (1992). Improved synthesis: H. B. Arzeno et al., Int. J. Pept. Protein Res. 41, 342 (1993). Degradation in aq soln: R. G. Strickley et al., Pharm. Res. 7, 530 (1990). Clinical pharmacology and pharmacokinetics: J. Rabinovici et al., J. Clin. Endocrinol. Metab. 75, 1220 (1992). Clinical trial in assisted fertilization: P. Devroey et al., Hum. Reprod. 13, 3023 (1998).

Derivative

Acetate.

Nomenclature

CAS number: 129311-55-3
Org-37462; RS-26306; Antagon (Organon); Orgalutran (Organon).
C80H113ClN18O13.2C2H4O2; mol wt 1690.42.
C 59.68%, H 7.21%, Cl 2.10%, N 14.91%, O 16.09%.

Properties

pKa: 4.2 (3-pyridinylalanine); 9.8 (tyrosine). Sol in water.

Therapeutic Category

In treatment of infertility.

Keywords

LH-RH Antagonist