Tafluprost

From WikiProjectMed
Jump to navigation Jump to search
Tafluprost
Tafluprost structure.svg
Names
Trade namesSaflutan, Taflotan, Tapros, Zioptan, others
  • 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]
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)
  • CC(C)OC(=O)CCC\C=C/CC(C(O)CC1O)C1\C=C\C(F)(F)COc2ccccc2
  • 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 F (PGF). 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 PGF 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. 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 "Tafluprost Monograph for Professionals". Drugs.com. Retrieved 20 September 2021.
  2. Canada, Health (2 July 2014). "Notice: Prescription Drug List (PDL): Multiple additions". www.canada.ca. Retrieved 20 September 2021.
  3. "Tafluprost Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 20 September 2021.
  4. "Prostaglandin Analogues for Ophthalmic Use: A Review of Comparative Clinical Effectiveness, Cost-Effectiveness, and Guidelines | CADTH". www.cadth.ca. Retrieved 20 September 2021.
  5. 5.0 5.1 Tafluprost Professional Drug Facts.
  6. 6.0 6.1 6.2 6.3 6.4 6.5 Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.CS1 maint: unrecognized language (link)
  7. 7.0 7.1 7.2 7.3 7.4 Dinnendahl V, Fricke U, eds. (2011). Arzneistoff-Profile (in German). 9 (25 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.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.

External links

Identifiers: