Travoprost

Travoprost
Names
Trade namesTravatan, Izba, others
IUPAC name
  • Propan-2-yl 7-[3,5-dihydroxy-2-[3-hydroxy-4-[3-(trifluoromethyl)
    phenoxy]-but-1-enyl]-cyclopentyl]hept-5-enoate
Clinical data
Pregnancy
category
  • AU: B3[1]
  • US: C (Risk not ruled out)[1]
    Routes of
    use    		Topical (eye drops)
    Onset of action2 hours
    Duration of action≥ 24 hours
    Defined daily dosenot established[2]
    External links
    AHFS/Drugs.comMonograph
    US NLMTravoprost
    MedlinePlusa602027
    Legal
    License data
    Legal status
    • US: ℞-only
    • In general: ℞ (Prescription only)
    Pharmacokinetics
    MetabolismActivation by ester hydrolysis, deactivation by beta oxidation, OH-oxidation, double bond reduction
    Elimination half-life1.5 hours (in aqueous fluid)
    45 minutes (terminal)
    ExcretionMainly via kidney
    Chemical and physical data
    FormulaC26H35F3O6
    Molar mass500.555 g·mol−1
    3D model (JSmol)
    SMILES
    • FC(F)(F)c2cc(OC[C@H](O)/C=C/[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(=O)OC(C)C)ccc2
    InChI
    • 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 checkY
    • Key:MKPLKVHSHYCHOC-AHTXBMBWSA-N checkY

    Travoprost, sold under the brand name Travatan among others, is medications used to treat high pressure inside the eye including glaucoma.[3] Specifically it is used for open angle glaucoma when other agents are not sufficient.[4][3] It is used as an eye drop.[3] Effects generally occur within 2 hours.[3]

    Common side effects include red eyes, blurry vision, eye pain, dry eyes, and change in color of the eyes.[3][4] Other significant side effects may include cataracts.[4] Use during pregnancy or breastfeeding is generally not recommended.[4] It is a prostaglandin analog and works by increasing the outflow of aqueous fluid from the eyes.[3]

    Travoprost was approved for medical use in the United States in 2001.[3] It is available as a generic medication in the United Kingdom.[4] A 2.5 milliliter bottle in the United Kingdom costs the NHS about 7.30 £ as of 2019.[4] In the United States the wholesale cost of this amount is about US$177.[5] In 2017, it was the 212th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

    Medical uses

    Travoprost is used to treat high pressure inside the eye including glaucoma.[3] Specifically it is used for open angle glaucoma when other agents are not sufficient.[4][3]

    Dosage

    The defined daily dose is not defined.[2]

    Side effects

    One 2.5 ml dropperette of travoprost

    Possible side effects are:[8]

    • blurred vision
    • eyelid redness
    • permanent darkening of eyelashes
    • eye discomfort
    • permanent darkening of the iris to brown (heterochromia)
    • burning sensation during use
    • thickening of the eyelashes
    • inflammation of the prostate gland, restricting urine flow (BPH)

    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.[9]

    Pharmacology

    Mechanism of action

    It is a synthetic prostaglandin analog (or more specifically, an analog of prostaglandin F2α)[10][11] that works by increasing the outflow of aqueous fluid from the eyes.[12]

    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.[8]

    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).[8]

    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[8] with a terminal half-life of 45 minutes.[13]

    Society and culture

    Cost

    A 2.5 milliliter bottle in the United Kingdom costs the NHS about 7.30 £ as of 2019.[4] In the United States the wholesale cost of this amount is about US$177.[5] In 2017, it was the 212th most commonly prescribed medication in the United States, with more than two million prescriptions.[6][7]

    • Travoprost costs (US)
    • Travoprost prescriptions (US)

    References

    1. 1 2 "Travoprost ophthalmic Use During Pregnancy". Drugs.com. 8 October 2019. Archived from the original on 25 January 2021. Retrieved 16 May 2020.
    2. 1 2 "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 5 August 2019. Retrieved 9 September 2020.
    3. 1 2 3 4 5 6 7 8 9 "Travoprost Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 27 March 2019. Retrieved 26 March 2019.
    4. 1 2 3 4 5 6 7 8 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 1152. ISBN 9780857113382.
    5. 1 2 "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Archived from the original on 2019-03-06. Retrieved 3 March 2019.
    6. 1 2 "The Top 300 of 2020". ClinCalc. Archived from the original on 18 March 2020. Retrieved 11 April 2020.
    7. 1 2 "Travoprost - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 11 April 2020.
    8. 1 2 3 4 Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Travatan 40 Mikrogramm/ml Augentropfen.{{cite book}}: CS1 maint: unrecognized language (link)
    9. ↑ Xu L, Wang X, Wu M (February 2017). "Topical medication instillation techniques for glaucoma". The Cochrane Database of Systematic Reviews. 2: CD010520. doi:10.1002/14651858.CD010520.pub2. PMC 5419432. PMID 28218404.
    10. ↑ Alcon Laboratories, Inc. (September 2011). "Travatan - travoprost solution". DailyMed. Bethesda, MD: U.S. National Library of Medicine. Archived from the original on 2012-03-10. Retrieved 2011-09-30.
    11. ↑ Alcon Laboratories, Inc. (September 2011). "Travatan Z (travoprost) solution". DailyMed. Bethesda, MD: U.S. National Library of Medicine. Archived from the original on 2012-03-10. Retrieved 2011-09-30.
    12. ↑ AHFS Consumer Medication Information (2011-01-01). "Travoprost Ophthalmic". MedlinePlus. Bethesda, MD: U.S. National Library of Medicine. Archived from the original on 2016-07-05. Retrieved 2011-09-30.
    13. ↑ Drugs.com: Travoprost Monograph.
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