15-epi Travoprost

• CAT Number: R053378
• CAS Number: 1420791-14-5
• Molecular Formula: C26H35F3O6
• Molecular Weight: 500.555
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
• InChI: InChI=1S/C26H35F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-24,30-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21+,22+,23-,24+/m0/s1
• InChIKey: MKPLKVHSHYCHOC-AURHPGDUSA-N
• SMILES: CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC=CC(=C2)C(F)(F)F)O)O)O

15(S)-<wbr></wbr>Fluprostenol isopropyl ester (15(S)-<wbr></wbr>Flu-<wbr></wbr>Ipr) is the unnatural C-<wbr></wbr>15 epimer of Travoprost. Travoprost is the Alcon trade name for fluprostenol isopropyl ester, (Flu-<wbr></wbr>Ipr) an F-<wbr></wbr>series prostaglandin analog which has been approved for use as an ocular hypotensive drug. Flu-<wbr></wbr>Ipr is a prodrug which is converted by esterase enzymatic activity in the cornea to yield the corresponding free acid. The free acid, fluprostenol, is a potent FP receptor agonist. In human and animal models of glaucoma, FP receptor agonist activity corresponds very closely with intraocular hypotensive activity. Although data is currently not available for the activity of 15(S)-<wbr></wbr>Flu-<wbr></wbr>Ipr, inversion of the stereochemistry at the 15 position of ocular hypotensive prostaglandins generally lowers the potency approximately 100 fold.