Tafluprost

Tafluprost

Clinical data
Trade names	Saflutan, Taflotan, Tapros, Zioptan
AHFS/Drugs.com	Multum Consumer Information
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical (eye drops)
ATC code	S01EE05 (WHO)
Legal status
Legal status	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-[(1E)-3,3-difluoro-4-phenoxybut-1-en-1-yl]-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 Y
ChEMBL	CHEMBL1963683
ECHA InfoCard	100.207.745
Chemical and physical data
Formula	C25H34F2O5
Molar mass	452.531266 g/mol
3D model (Jmol)	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 and Zioptan by Merck in the US) 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.

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.

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.

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.