Travoprost

Overview

Travoprost, sold under the brand name Travatan among others, is a medication used to treat high pressure inside the eye including glaucoma. Specifically it is used for open angle glaucoma when other agents are not sufficient. It is used as an eye drop. Effects generally occur within two hours.[1][2] WP

Common side effects include red eyes, blurry vision, eye pain, dry eyes, and change in color of the eyes. Other significant side effects may include cataracts. Use during pregnancy or breastfeeding is generally not recommended. It is a prostaglandin analog and works by increasing the outflow of aqueous fluid from the eyes.[1][2] WP

Travoprost was approved for medical use in the United States and in the European Union in 2001. It is available as a generic medication in the United Kingdom. In 2020, it was the 304th most commonly prescribed medication in the United States, with more than 1 million prescriptions.[1–5] WP

Uses, dosage and effects

Medical uses

Travoprost is used to treat high pressure inside the eye including glaucoma. Specifically it is used for open angle glaucoma when other agents are not sufficient.[1][2] WP

Risks and side effects

Side effects

Possible side effects are:[6] WP

• blurred vision[6] WP
• eyelid redness[6] WP
• permanent darkening of eyelashes[6] WP
• eye discomfort[6] WP
• permanent darkening of the iris to brown (heterochromia)[6] WP
• burning sensation during use[6] WP
• thickening of the eyelashes[6] WP
• inflammation of the prostate gland, restricting urine flow (BPH)[6] WP⚠ Wikipedia itself has flagged this text: citation needed.

Research suggests that wiping the eye with an absorbent pad after the administration of eye drops can result in shorter eyelashes and a lesser chance of hyperpigmentation in the eyelid, compared to not wiping off excess fluid.[7] WP

Pharmacology

Mechanism of action

It is a synthetic prostaglandin analog (or more specifically, an analog of prostaglandin F2α) that works by increasing the outflow of aqueous fluid from the eyes.[8][9][10] WP

Like other analogs of prostaglandin F2α such as tafluprost and latanoprost, travoprost is an ester prodrug of the free acid, which acts as an agonist at the prostaglandin F receptor, increasing outflow of aqueous fluid from the eye and thus lowering intraocular pressure.[6] WP

Pharmacokinetics

Travoprost is absorbed through the cornea, where it is hydrolysed to the free travoprost acid. Highest concentrations of the acid in the eye are reached one to two hours after application, and its half-life in the aqueous fluid is 1.5 hours. Once it reaches the bloodstream, it is quickly metabolised, so that concentrations in the system do not exceed 25 pg/ml (compared to 20 ng/ml in the eye, which is higher by nearly a factor of 1000). Metabolites are formed by beta oxidation of the acidic chain (compare Tafluprost#Pharmacokinetics), oxidation of the OH-group in the other side chain, and reduction of the double bond next to this OH-group. Travoprost acid and its metabolites are mainly excreted via the kidney with a terminal half-life of 45 minutes.[6][11] WP

Chemistry

Formula

C26H35F3O6 PC

CAS number

157283-68-6 PC

Molar mass (g/mol)

500.5 PC

IUPAC name (computed by PubChem)

propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate PC

SMILES

CC(C)OC(=O)CCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](COC2=CC=CC(=C2)C(F)(F)F)O)O)O PC

InChIKey

MKPLKVHSHYCHOC-AHTXBMBWSA-N PC

PubChem CID

5282226

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Travoprost Monograph for Professionals
2. Other British national formulary: BNF 76. 2018
3. Journal / agency Travatan EPAR. 10 July 2007
4. Other The Top 300 of 2020
5. Other Travoprost - Drug Usage Statistics
6. Other Austria-Codex. 2015
7. Journal / agency Xu L, Wang X, Wu M. Topical medication instillation techniques for glaucoma. The Cochrane Database of Systematic Reviews. February 2017. doi:10.1002/14651858.CD010520.pub2 · PMID 28218404 · PMC5419432
8. Journal / agency Alcon Laboratories, Inc. Travatan - travoprost solution. September 2011
9. Journal / agency Alcon Laboratories, Inc. Travatan Z (travoprost) solution. September 2011
10. Journal / agency AHFS Consumer Medication Information. Travoprost Ophthalmic. 1 January 2011
11. Other Drugs.com: Travoprost drugs.com monograph travoprost

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.