9577. Travoprost

Nomenclature

CAS number: 157283-68-6
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic acid 1-methylethyl ester; (+)-16-[3-(trifluoromethyl)phenoxy]-17,18,19,20-tetranorprostaglandin F2α isopropyl ester; (+)-9α,11α,15-trihydroxy-16-(3-trifluoromethylphenoxy)-17,18,19,20-tetranor-5-cis-13-trans-prostadienoic acid isopropyl ester; AL-6221; Travatan (Alcon).
C26H35F3O6; mol wt 500.55.
C 62.39%, H 7.05%, F 11.39%, O 19.18%.

Description and references

Selective FP prostaglandin receptor agonist. Isopropyl ester of (+)-fluprostenol, q.v. General prepn (not claimed): J. W. Stjernschantz, EP 364417 (1989 to Pharmacia). Large scale synthesis: L. T. Boulton et al., Org. Process Res. Dev. 6, 138 (2002). Pharmacology: M. R. Hellberg et al., J. Ocul. Pharmacol. Ther. 17, 421 (2001). LC/MS/MS determn in plasma: B. A. McCue et al., J. Pharm. Biomed. Anal. 28, 199 (2002). Ocular hypotensive effects in dogs: A. B. Carvalho et al., Vet. Ophthalmol. 9, 121 (2006). Clinical trial in glaucoma or ocular hypertension: R. L. Fellman et al., Ophthalmology 109, 998 (2002); in combination with timolol: J. S. Schuman et al., Am. J. Ophthalmol. 140, 242-250 (2005).

Chemical structure

Properties

Colorless oil. [α]D20 +14.6° (c = 1.0 in methylene chloride). Very sol in acetonitrile, methanol, octanol, chloroform. Practically insol in water.

Therapeutic Category

Antiglaucoma.

Therapeutic Category (Veterinary)

Antiglaucoma.

Keywords

Antiglaucoma