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Tafluprost

Clinical data
Trade names	Saflutan, Taflotan, Zioptan
AHFS/Drugs.com	Multum Consumer Information
Routes of administration	Topical eye drops
ATC code	S01EE05 (WHO)
Legal status
Legal status	CA: ℞-only US: ℞-only
Pharmacokinetic data
Metabolism	Activation by ester hydrolysis, deactivation by beta oxidation
Onset of action	2–4 hrs
Duration of action	≥ 24 hrs
Identifiers
IUPAC name Isopropyl (5Z)-7-{(1R,2R,3R,5S)-2--3,5-dihydroxycyclopentyl}hept-5-enoate
CAS Number	209860-87-7
PubChem CID	6433101
DrugBank	DB08819
ChemSpider	8044182
UNII	1O6WQ6T7G3
KEGG	D06274
ChEBI	CHEBI:66899
ChEMBL	ChEMBL1963683
CompTox Dashboard (EPA)	DTXSID401021504
ECHA InfoCard	100.207.745
Chemical and physical data
Formula	C25H34F2O5
Molar mass	452.539 g·mol
3D model (JSmol)	Interactive image
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 (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.

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.

Interactions

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

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

Pharmacology

Mechanism of action

Tafluprost is a prodrug of the active substance, tafluprost acid, a structural and functional analogue of prostaglandin F_2α (PGF_2α). Tafluprost acid is a selective agonist at the prostaglandin F receptor, increasing outflow of aqueous fluid from the eyes and thus lowering intraocular pressure.

Other PGF_2α analogues with the same mechanism include latanoprost and travoprost.

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.

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.

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

References

1. "Product monograph" (PDF). hres.ca. Retrieved 6 April 2024.
2. ^ Tafluprost Professional Drug Facts.
3. ^ Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
4. ^ 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.
5. 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.
6. 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.

• Prostaglandins
• Secondary alcohols
• Alkene derivatives
• Drugs developed by Merck & Co.
• Carboxylate esters
• Isopropyl esters
• Organofluorides
• Phenol ethers
• Ophthalmology drugs