Tafluprost

Tafluprost
Names
Trade namesSaflutan, Taflotan, Tapros, Zioptan, others
IUPAC name
  • Isopropyl (5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate
Clinical data
Drug classProstaglandin analogue[1]
Main usesOpen-angle glaucoma, ocular hypertension[1]
Side effectsEye redness, itchiness, eyelash growth, blurry vision[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: C (Risk not ruled out)
    Routes of
    use    		Topical (eye drops)
    Onset of action2–4 hrs
    Duration of action≥ 24 hrs
    External links
    AHFS/Drugs.comMultum Consumer Information
    Legal
    Legal status
    Pharmacokinetics
    MetabolismActivation by ester hydrolysis, deactivation by beta oxidation
    Chemical and physical data
    FormulaC25H34F2O5
    Molar mass452.539 g·mol−1
    3D model (JSmol)
    SMILES
    • CC(C)OC(=O)CCC\C=C/CC(C(O)CC1O)C1\C=C\C(F)(F)COc2ccccc2
    InChI
    • InChI=1S/C25H34F2O5/c1-18(2)32-24(30)13-9-4-3-8-12-20-21(23(29)16-22(20)28)14-15-25(26,27)17-31-19-10-6-5-7-11-19/h3,5-8,10-11,14-15,18,20-23,28-29H,4,9,12-13,16-17H2,1-2H3/b8-3-,15-14+/t20-,21-,22+,23-/m1/s1
    • Key:WSNODXPBBALQOF-VEJSHDCNSA-N

    Tafluprost, sold under the brand name Zioptan among others, is a medication used to treat open-angle glaucoma and ocular hypertension.[1] It is used as an eye drop.[1] It may be used alone or with other medications.[1]

    Common side effects include eye redness, itchiness, eyelash growth, and blurry vision.[1] Other side effects may include iritis and macular edema.[1] It is a prostaglandin analogue which is believed to work by increasing the outflow of aqueous fluid from the eye.[1]

    Tafluprost was approved for medical use in the United States in 2012 and Canada in 2014.[1][2] In the United States it costs about 150 USD per month as of 2021.[3] In Canada it was less cost effective as compared to bimatoprost in 2020.[4]

    Medical uses

    It is used to treat open-angle glaucoma and ocular hypertension.[1]

    Dosage

    It is used as one drop once per day of a 0.0015% solution.[1]

    Side effects

    The most common side effect is conjunctival hyperemia, which occurs in 4 to 20% of patients. Less common side effects include stinging of the eyes, headache, and respiratory infections. Rare side effects are dyspnoea (breathing difficulties), worsening of asthma, and macular oedema.[5][6][7]

    Interactions

    Nonsteroidal anti-inflammatory drugs (NSAIDs) can either reduce or increase the effect of tafluprost.[5] Timolol eye drops, a common kind of glaucoma medication, does not negatively interact with this drug.[6]

    No interactions with systemic (for example, oral) drugs are expected because tafluprost does not reach relevant concentrations in the bloodstream.[6][7]

    Pharmacology

    Mechanism of action

    Tafluprost is a prodrug of the active substance, tafluprost acid, a structural and functional analogue of prostaglandin F2α (PGF2α). Tafluprost acid is a selective agonist at the prostaglandin F receptor, increasing outflow of aqueous fluid from the eyes and thus lowering intraocular pressure.[6][7]

    Other PGF2α analogues with the same mechanism include latanoprost and travoprost.[6]

    Pharmacokinetics

    Tafluprost, as a lipophilic ester, easily penetrates the cornea and is then activated to the carboxylic acid, tafluprost acid. Onset of action is 2 to 4 hours after application, the maximal effect is reached after 12 hours, and ocular pressure remains lowered for at least 24 hours.[6][7]

    Tafluprost acid is inactivated by beta oxidation to 1,2-dinortafluprost acid, 1,2,3,4-tetranortafluprost acid, and its lactone, which are subsequently glucuronidated or hydroxylated. The cytochrome P450 liver enzymes play no role in the metabolism.[7]

    An analogous pathway (at least up to the tetranor-metabolites) has been found for latanoprost and travoprost.

    Metabolism. From left to right: tafluprost, tafluprost acid (the active metabolite), 1,2-dinortafluprost acid, 1,2,3,4-tetranortafluprost acid, 1,2,3,4-tetranortafluprost acid lactone[8][9]
    A tafluprost/timolol combination ophthalmic solution

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 12 "Tafluprost Monograph for Professionals". Drugs.com. Archived from the original on 4 March 2021. Retrieved 20 September 2021.
    2. ↑ Canada, Health (2 July 2014). "Notice: Prescription Drug List (PDL): Multiple additions". www.canada.ca. Archived from the original on 8 July 2021. Retrieved 20 September 2021.
    3. ↑ "Tafluprost Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 1 May 2016. Retrieved 20 September 2021.
    4. ↑ "Prostaglandin Analogues for Ophthalmic Use: A Review of Comparative Clinical Effectiveness, Cost-Effectiveness, and Guidelines | CADTH". www.cadth.ca. Archived from the original on 22 September 2021. Retrieved 20 September 2021.
    5. 1 2 Tafluprost Professional Drug Facts.
    6. 1 2 3 4 5 6 Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.{{cite book}}: CS1 maint: unrecognized language (link)
    7. 1 2 3 4 5 Dinnendahl V, Fricke U, eds. (2011). Arzneistoff-Profile (in German). Vol. 9 (25 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.{{cite book}}: CS1 maint: unrecognized language (link)
    8. ↑ Fukano Y, Kawazu K (August 2009). "Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats". Drug Metabolism and Disposition. 37 (8): 1622–34. doi:10.1124/dmd.108.024885. PMID 19477946. S2CID 12425702.
    9. ↑ Fukano Y, Kawazu K, Akaishi T, Bezwada P, Pellinen P (June 2011). "Metabolism and ocular tissue distribution of an antiglaucoma prostanoid, tafluprost, after ocular instillation to monkeys". Journal of Ocular Pharmacology and Therapeutics. 27 (3): 251–9. doi:10.1089/jop.2010.0178. PMID 21491995.
    Identifiers:
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