Advertisement

Prodrugs pp 1359-1368 | Cite as

Case Study: Travoprost: A Potent PGF2α Analog

  • Rebecca A. Bross
Part of the Biotechnology: Pharmaceutical Aspects book series (PHARMASP, volume V)

Abstract

Travoprost, an analog of prostaglandin PGF, was designed to be a potent agent for lowering intraocular pressure (IOP) as well as a selective FP prostaglandin receptor agonist in the treatment of glaucoma.

Keywords

Aqueous Humor Ocular Hypertension Prostaglandin Analog Ester Prodrug Isopropyl Ester 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Alcon Laboratories. Travatan (product insert). Alcon Laboratories, Inc. 2004 Google Scholar
  2. Alexander CL, Miller SJ, and Abel SR. Prostaglandin Analog Treatment of Glaucoma and Ocular Hypertension. Ann Pharmacother 2002; 36:504–511PubMedCrossRefGoogle Scholar
  3. Al-Jazzaf AM, DeSantis L, and Netland PA. Travoprost: A Potent Ocular Hypotensive Agent. Drugs Today 2003; 39:61–74PubMedCrossRefGoogle Scholar
  4. Anonymous. The Eyes Have It. Spec Chem Mag 2002; 22:12–13Google Scholar
  5. Anonymous. Scientific Discussion: Travatan. European Agency for the Evaluation of Medicinal Products [online]. Available from URL: www.emea.eu.int.htm [Accessed 2004 March]Google Scholar
  6. Bito LZ. Comparison of the Ocular Hypotensive Efficacy of Esicosanoids and Related Compounds. Exp Eye Res 1984; 38:181–194PubMedCrossRefGoogle Scholar
  7. Bito LZ, and Baroody RA. The Ocular Pharmacokinetic of Eicosanoids and Their Derivatives. 1. Comparisons of Ocular Eicosanoid Penetration and Distribution Following the Topical Application of PGF2α, PGF2α-1-methyl ester, and PGF2α-1-isopropyl ester. Exp Eye Res 1987; 44:217–226PubMedCrossRefGoogle Scholar
  8. Boulton LT., Brick D, Fox ME, Jackson M, Lennon IC, McCague R, Parkin N, Rhodes D, and Ruecroft G. Synthesis of the Potent Anti-glaucoma Agent, Travoprost. Org Process Res Dev 2002; 6:138–145.CrossRefGoogle Scholar
  9. Brubaker RF. Flow of Aqueous Humor in Humans: The Friedenwald Lecture. Invest Opth Vis Sci 1991; 32:3145–3165Google Scholar
  10. Camber O, and Edman P. Factors Influencing the Corneal Permeability of Prostaglandin F2 and Its Isopropyl Ester in vitro. Int J Pharm 1987; 37:27–32CrossRefGoogle Scholar
  11. Cheng-Bennett A, Chan MF, Chen G, Gac T, Garst ME, Gluchowski C, Kaplan LJ, Protzman CE, Roof MB, and Sachs G. Studies on a Novel Series of Acyl Ester Prodrugs of Prostaglandin F2 alpa. Br J Ophthalmol 1994; 78:560–567PubMedCrossRefGoogle Scholar
  12. Eisenberg, DL, Toris CB, and Camras CB. Bimatroprost and Travoprost: a Review of Recent Studies of Two New Glaucoma Drugs. Surv Ophthalmol 2002; 47(Suppl 1):S105–115PubMedCrossRefGoogle Scholar
  13. Feldman RM. Conjunctival Hyperemia and the Use of Topical Prostaglandins in Glaucoma and Ocular Hypertension. J Ocul Pharmacol Ther 2003; 19:23–34PubMedCrossRefGoogle Scholar
  14. Giuffré G. The Effects of Prostaglandin F2α in the Human Eye. Grafés Arch Clin Exp Ophthalmol 1985; 222:139–141CrossRefGoogle Scholar
  15. Hellberg MR, and Nixon JC. Use of Non-steroidal Anti-inflammatory Agents in Combination with Prostaglandin FP Receptor Agonist to Treat Glaucoma and Ocular Hypertension. U.S. Patent #2002103255 (August 1) 2002Google Scholar
  16. Hellberg MR, Sallee VL, McLaughlin MA, Sharif NA, Desantis L, Dean TR, and Zinke PW. Preclinical Efficacy of Travoprost, a Potent and Selective FP Prostaglandin Receptor Agonist. J Ocul Pharmacol 2001; 17:421–432CrossRefGoogle Scholar
  17. Hellberg MR, McLaughlin MA, Sharif NA, DeSantis L, Dean TR, Kyba, EP, Bishop JE, Klimko PG, Zinke PW, Selliah RD, Barnes G, DeFaller J, Kothe A, Landry T, Sullivan EK, Andrew R, Davis AA, Silver L, Bergamini MVW, Robertson S, Weiner Al, and Sallee VL. Identification and Characterization of the Ocular Hypotensive Efficacy of Travoprost, a Potent and Selective FP Prostaglandin Receptor Agonist, and AL-6598, a DP Prostaglandin Receptor Agonist. Surv Ophthalmol 2002; 47(Supplement):S13–S33PubMedCrossRefGoogle Scholar
  18. Hoyng PF, and Kitazawa Y. Medical Treatment of Normal Tension Glaucoma. Surv Ophthalmol 2002; 47(Supplement 1):S116–S124PubMedCrossRefGoogle Scholar
  19. Hylton C, and Robin AL. Update on Prostaglandin Analogs. Curr Opin Opththalmol 2003; 14:65–69CrossRefGoogle Scholar
  20. Jackson PM, and Lennon IC. Novel Intermediate for the Synthesis of Prostaglandins. PCT Int Appl.# 2000061588 (October 19) 2000.Google Scholar
  21. Kararli TT, Bandyopadhyay R, Singh SK, and Hawley LC. Ophthalmic Formulation of a Selective Cyclooxygenase-2 Inhibitory Drug. PCT Int Appl. # 2002005815 (January 24) 2002.Google Scholar
  22. Lindén C, and Alm A. Prostaglandin Analogs in the Treatment of Glaucoma. Drugs Aging 1999; 14:387–398PubMedCrossRefGoogle Scholar
  23. Orengo-Nania S, Landry T, Von Tress M, Silver LH, Weiner A, Davis AA, and Travoprost study group. Evaluation of Travoprost and Adjunctive Therapy in Patients with Uncontrolled Intraocular Pressure while using Timolol 0.5%. Am J Ophthalmol 2001; 132:860–868.PubMedCrossRefGoogle Scholar
  24. Quigley HA. Number of People With Glaucoma Worldwide. Br J Ophthalmol 1996; 80:389–393PubMedCrossRefGoogle Scholar
  25. Robertson SM. Improved Prostanoid Therapies for the Treatment of Glaucoma. PCT Int Appl. # 2002072105 (September 19) 2002Google Scholar
  26. Schachtschabel U, Lindsey JD, and Weinreb RN. The Mechanism of Action of Prostaglandins on Uveoscleral Outflow. Curr Opin Opththalmol 2000; 11:112–115.CrossRefGoogle Scholar
  27. Schneider L, Wayne BR, and Weiner, AL. Storage-stable Prostaglandin Compositions. U.S. Patent # 6011062 (January 4) 2000.Google Scholar
  28. Sharif NA, Davis TL, and Williams GW. [3H]AL-5848 ([3H]9β-(+)-Fluprostenol. Carboxylic Acid of Travoprost (AL-6221), a Novel FP Prostaglandin Study the Pharmacology and Autoradiographic Localization of the FP Receptor. J Pharm Pharmacol 1999; 51:685–694PubMedCrossRefGoogle Scholar
  29. Sharif NA, Kelly CR, and Crider JY. Agonist Activity of Bimatoprost, Travoprost, Lantanoprost, Unoprostone Isopropyl Ester and Other Prostaglandin Analogs at the Cloned Human Ciliary Body FP Prostaglandin Receptor. J Ocular Pharm Ther 2002; 18:313–324CrossRefGoogle Scholar
  30. Sorbera LA, and Castaner K. Travoprost: Antiglaucoma, Prostaglandin FP Agonist. Drug Future 2000; 25:41–45.CrossRefGoogle Scholar
  31. Stjernschantz J, and Resul B. Anti-inflammatory Agents for Preventing Increased Iridial Pigmentation During Prostaglandin Treatment. PCT Int Appl# 2000025771 (May 11) 2000.Google Scholar
  32. Waugh J, and Jarvis B. Travoprost. Drugs Aging 2002; 19:465–471PubMedCrossRefGoogle Scholar
  33. Weiner AL, Airy SC, Yarborough C, Clifford JA, and McCune WE. Prostaglandin Formulations Stability in Polypropylene Containers. PCT Int Appl # 2000003736 (January 27) 2000.Google Scholar
  34. Whitson JT. Travoprost—A New Prostaglandin Analog for the Treatment of Glaucoma. Expert Opin Pharmacol 2002; 3:965–977CrossRefGoogle Scholar

Copyright information

© American Association of Pharmaceutical Scientists 2007

Authors and Affiliations

  • Rebecca A. Bross
    • 1
  1. 1.Department of Pharmaceutical ChemistryThe University of KansasLawrenceUSA

Personalised recommendations