Product Name

Travoprost

CAS Number

157283-68-6

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Product Name:
Travoprost
CAS Number:
157283-68-6
Indication:
Ophthalmic solution used for the reduction of elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension who are intolerant of other intraocular pressure lowering medications or insufficiently responsive (failed to achieve target IOP determined after multiple measurements over time) to another intraocular pressure lowering medication.
Mode of Action:

Travoprost free acid is a selective FP prostanoid receptor agonist and is believed to reduce intraocular pressure by increasing the drainage of aqueous humor, which is done primarily through increased uveoscleral outflow and to a lesser extent, trabecular outflow facility.

Pharmacodynamics:

Travoprost, an isopropyl ester prodrug, is a synthetic prostaglandin F2 alpha analogue that is rapidly hydrolyzed by esterases in the cornea to its biologically active free acid. The travoporst free acid is potent and highly selective for the FP prostanoid receptor.

Metabolism:

Travoprost, an isopropyl ester prodrug, is hydrolyzed by esterases in the cornea to its biologically active free acid. Systemically, travoprost free acid is metabolized to inactive metabolites via beta-oxidation of the _(carboxylic acid) chain to give the 1, 2-dinor and 1, 2, 3, 4-tetranor analogs, via oxidation of the 15-hydroxyl moiety, as well as via reduction of the 13, 14 double bond.

Toxicity:

Symptoms of overexposure include irritation to the skin, eyes, nose, throat, and respiratory tract.

IUPAC:
5-Heptenoic acid, 7-((1R, 2R, 3R, 5S)-3, 5-dihydroxy-2-((1E, 3R)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)-1-butenyl)cyclopentyl)-, 1-methylethyl ester, (5Z)-
ATC:
S01EE04
PubChem:
656627
DrugBank:
DB00287 (APRD01271)
Formula:
C26-H35-F3-O6
Molecular Mass:
500.551
Synonyms:
isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-{(1E,3R)-3-hydroxy-4-[(α,α,α-trifluoro-m-tolyl)oxy]-1-butenyl}cyclopentyl)-5-heptenoate, Travoprost, Travoprostum

SMILES:
C1[C@H]([C@@H]([C@H]([C@H]1O)CC=CCCCC(OC(C)C)=O)C=C[C@@H](COc1cc(ccc1)C(F)(F)F)O)O
AHFS Code:
53:32.0
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-/m1/s1
General Reference:
General Reference:

1. Lim KS, Nau CB, O’Byrne MM, Hodge DO, Toris CB, McLaren JW, Johnson DH: Mechanism of action of bimatoprost, latanoprost, and travoprost in healthy subjects. A crossover study. Ophthalmology. 2008 May;115(5):790-795.e4. doi: 10.1016/j.ophtha.2007.07.002. [PubMed:18452763]
2. Costagliola C, dell’Omo R, Romano MR, Rinaldi M, Zeppa L, Parmeggiani F: Pharmacotherapy of intraocular pressure – part II. Carbonic anhydrase inhibitors, prostaglandin analogues and prostamides. Expert Opin Pharmacother. 2009 Dec;10(17):2859-70. doi: 10.1517/14656560903300129. [PubMed:19929706]
3. Ferrari G, Scagliotti GV: Serum and urinary vascular endothelial growth factor levels in non-small cell lung cancer patients. Eur J Cancer. 1996 Dec;32A(13):2368-9. [PubMed:9038626]
4. Toris CB, Gabelt BT, Kaufman PL: Update on the mechanism of action of topical prostaglandins for intraocular pressure reduction. Surv Ophthalmol. 2008 Nov;53 Suppl1:S107-20. doi: 10.1016/j.survophthal.2008.08.010. [PubMed:19038618]
5. Arranz-Marquez E, Teus MA: Prostanoids for the management of glaucoma. Expert Opin Drug Saf. 2008 Nov;7(6):801-8. doi: 10.1517/14740330802465474 . [PubMed:18983226]
6. Electronic Medicines Compendium: Travatan (travoprost) Monograph [Link]
7. Alcon treatment Travatan® receives EU approval for pediatric glaucoma patients: Press Release [Link]
8. Alcon receives FDA approval for first-line use of Travatan Z: Press Release [Link]
9. Travatan Z (travoprost) FDA Label [File]
10. Travoprost Canadian Product Information [File]

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