Tafluprost
Chemical compound
- S01EE05 (WHO)
- CA: ℞-only[1]
- US: ℞-only
- Isopropyl (5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-3,5-dihydroxycyclopentyl}hept-5-enoate
- 209860-87-7
- 6433101
- DB08819
- 8044182
- 1O6WQ6T7G3
- D06274
- CHEBI:66899
Y
- ChEMBL1963683
- Interactive image
- 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 (trade names Taflotan by Santen Pharmaceutical, Zioptan by Merck in the US and Saflutan by Mundipharma in Australia) is a prostaglandin analogue. It is used topically (as eye drops) to control the progression of open-angle glaucoma and in the management of ocular hypertension, alone or in combination with other medication. It reduces intraocular pressure by increasing the outflow of aqueous fluid from the eyes.[2][3]
Adverse 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.[2][3][4]
Interactions
Nonsteroidal anti-inflammatory drugs (NSAIDs) can either reduce or increase the effect of tafluprost.[2] Timolol eye drops, a common kind of glaucoma medication, does not negatively interact with this drug.[3]
No interactions with systemic (for example, oral) drugs are expected because tafluprost does not reach relevant concentrations in the bloodstream.[3][4]
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.[3][4]
Other PGF2α analogues with the same mechanism include latanoprost and travoprost.[3]
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.[3][4]
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.[4]
An analogous pathway (at least up to the tetranor-metabolites) has been found for latanoprost and travoprost.
References
- ^ "Product monograph" (PDF). hres.ca. Retrieved 6 April 2024.
- ^ a b c Tafluprost Professional Drug Facts.
- ^ a b c d e f g Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
- ^ a b c d e 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.
- ^ 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.
- ^ 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.
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| Prostaglandins (PG) |
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| Thromboxanes (TX) |
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| Precursor | |
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| Initial |
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| SRS-A |
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| Precursor |
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| Eoxins |
|
- Lipoxins (LX) (A4, B4)
- Virodhamine
- bronchoconstriction
- PGD2
- TXA2
- LTC4
- LTD4
- LTE4
- vasoconstriction
- PGF2α
- TXA2
- TXB2
- vasodilation
- PGE2
- PGI2
- LTC4
- LTD4
- LTE4
- platelets: induce
- TXA2
- inhibit
- PGD2
- PGI2
- leukocytes: induce
- TXA2
- LTB4
- inhibit
- PGD2
- PGE2
- fever stimulation:
- PGE2
- labor stimulation:
- PGE2 (Dinoprostone)
- PGF2α (Dinoprost)
