Contents

Tafluprost

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[1] 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
CompTox Dashboard (EPA)	DTXSID401021504
ECHA InfoCard	100.207.745
Chemical and physical data
Formula	C25H34F2O5
Molar mass	452.539 g·mol−1
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 TaflotanbySanten Pharmaceutical, Zioptan by Merck in the US and Saflutan by Mundipharma in Australia) is a prostaglandin analogue. It is used topically (aseye 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]

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]

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]

Tafluprost is a prodrug of the active substance, tafluprost acid, a structural and functional analogueofprostaglandin 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.^[3][4]

Other PGF_2α analogues with the same mechanism include latanoprost and travoprost.^[3]

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 glucuronidatedorhydroxylated. 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.