10389. Tafluprost

Nomenclature

CAS number: 209860-87-7
(5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-Difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid 1-methylethyl ester; 16-phenoxy-15-deoxy-15,15-difluoro-17,18,19,20-tetranorprostaglandin F2α isopropyl ester; AFP-168; Taflotan (Santen); Tapros (Santen).
C25H34F2O5; mol wt 452.53.
C 66.35%, H 7.57%, F 8.40%, O 17.68%.

Description and references

Fluorinated prostaglandin derivative; ester prodrug that reduces intraocular pressure. Prepn: E. Shirasawa et al., EP 850926; eidem, US 5886035 (1998, 1999 both to Asahi Glass and Santen); Y. Matsumura et al., Tetrahedron Lett. 45, 1527 (2004) DOI. Pharmacology: Y. Takagi et al., Exp. Eye Res. 78, 767 (2004) DOI PubMed. Clinical pharmacokinetics and tolerability: A. Sutton et al., Int. J. Clin. Pharmacol. Ther. 46, 400 (2008) PubMed.

Chemical structure

Properties

Sol in methyl acetate, ethanol, DMSO, DMF. Sparingly sol in aqueous buffers.

Therapeutic Category

Antiglaucoma.

Keywords

Antiglaucoma