17-phenyl trinor Prostaglandin F2α

• CAT Number: R065360
• CAS Number: 38344-08-0
• Molecular Formula: C23H32O5
• Molecular Weight: 388.504
• Purity: ≥95%
• Synonyms: Bimatoprost (free acid);17-phenyl trinor PGF2α
• Storage: -20°C
• IUPAC Name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoic acid
• InChI: InChI=1S/C23H32O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,18-22,24-26H,2,7,10-13,16H2,(H,27,28)/b6-1-,15-14+/t18-,19+,20+,21-,22+/m0/s1
• InChIKey: YFHHIZGZVLHBQZ-KDACTHKWSA-N
• SMILES: C1C(C(C(C1O)C=CC(CCC2=CC=CC=C2)O)CC=CCCCC(=O)O)O

17-phenyl trinor Prostaglandin F2α (17-phenyl trinor PGF2α) is a metabolically stable analog of PGF2α and is a potent agonist for the FP receptor. It binds to the FP receptor on ovine luteal cells with a relative potency of 756% compared to that of PGF2α. At the rat recombinant FP receptor expressed in CHO cells bimatoprost inhibits PGF2α binding with a Ki of 1.1 nM. The isopropyl ester of 17-phenyl trinor PGF2α ethyl amide is slightly better than PGF2α isopropyl ester in reducing the intraocular pressure in the cat eye without any irritation.

Reference

1.Balapure, A.K.,Rexroad, C.E., Jr.,Kawada, K., et al. Structural requirements for prostaglandin analog interaction with the ovine corpus luteum prostaglandin F2α receptor. Biochemical Pharmacology 38, 2375-2381 (1989).