Tafluprost

S01E - Antiglaucoma preparations and miotics ATC S01EE05 Small molecule approved 2012 Topical Prodrug

Active form: Tafluprost Acid.

JFDA label: Saflutan 15mcg/ml Eye Drops

Mechanism of Action

Agonist of Prostaglandin F2-alpha receptor — Prostanoid FP receptor agonist

Target	Action	Gene / class
Prostaglandin F2-alpha receptor efficacy	AGONIST	PTGFR

Indications

Approved

Elevated intraocular pressure

Contraindications

Source: Lexicomp

There are no contraindications listed in the manufacturer’s prescribing information Absolute

Adverse Reactions

Very Common >10%Common 1–10%Uncommon 0.1–1% Rare 0.01–0.1%Very Rare <0.01%Not Known

Nervous system disorders (1)

Common Headache

Renal and urinary disorders (1)

Common Urinary tract infection

Eye disorders (9)

Common blurred vision · cataract · conjunctivitis · Eye irritation · eye pain · hyperpigmentation of eyelashes · increased eyelash length · stinging of eyes · xerophthalmia

Infections and infestations (1)

Common Common cold

Other (1)

Very Common Ophthalmic: Conjunctival hyperemia

Respiratory, thoracic and mediastinal disorders (1)

Common Cough

Dosing

Source: Lexicomp

Elevated intraocular pressure: Ophthalmic: One drop in the affected eye(s) once daily in the evening; do not exceed the once daily dosage because it has been shown that more frequent administration may decrease the IOP-lowering effect

Refer to adult dosing.

There are no dosage adjustments provided in the manufacturer’s labeling.

Warnings & Precautions

Source: Lexicomp

Ocular effects

May change/increase brown pigmentation of the iris, eyelid, and eyelashes; length, color, thickness, shape, and/or number of eyelashes may also be increased. Pigmentation of the iris is likely to be permanent although iris color change may not be noticeable for months to years; pigmentation of the eyelid and eyelash changes may be reversible following discontinuation of therapy. Long-term consequences and potential injury to eye are not known. Disease-related concerns:

Ocular disease

Use with caution in patients with intraocular inflammation, aphakic patients, pseudophakic patients with a torn posterior lens capsule, or patients with risk factors for macular edema. Special populations:

Pediatric

Use in pediatric patients is not recommended due to possible safety issues of increased pigmentation following long-term use.

Pregnancy & Lactation

Pregnancy

FDA category C

Adverse events have been observed in animal reproduction studies. Effective contraception during treatment is recommended for women of childbearing potential.

Lactation

It is not known if tafluprost is excreted in breast milk. The manufacturer recommends that caution be exercised when administering tafluprost to breast-feeding women.

Monitoring

Clinical pearl	Intraocular pressure; regularly examine patients who develop increased iris pigmentation

Chemistry & Properties

Formula	C25H34F2O5
Molecular weight	452.54 g/mol
IUPAC name	propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
CAS	209860-87-7
PubChem CID	9868491
InChIKey	`WSNODXPBBALQOF-VEJSHDCNSA-N`
logP	4.68 (XLogP 4.5)
Polar surface area	75.99 Å²
H-bond acceptors / donors	5 / 2
Drug-likeness (QED)	0.27
Lipinski violations	0

SMILES

CC(C)OC(=O)CCC/C=C\C[C@@H]1[C@@H](/C=C/C(F)(F)COc2ccccc2)[C@H](O)C[C@@H]1O

Biology & Pharmacokinetics

Pharmacokinetics predicted

Bioavailability	70.0%
Half-life	0.67 h
Volume of distribution	1.301 L/kg
Protein binding	92.3%
BBB penetrant	No

Enzyme interactions

Enzyme	Role	Detail
CYP2B6	Inhibitor	—
CYP2C19	Inhibitor	—
CYP2C19	Substrate	—
CYP2C8	Inhibitor	—
CYP2C9	Inhibitor	—
CYP3A4	Inhibitor	—
CYP3A4	Substrate	—

Transporters

BCRP (Inhibitor)BSEP (Inhibitor)MRP1 (Inhibitor)OATP1B1 (Inhibitor)OATP1B3 (Inhibitor)P-gp (Inhibitor)P-gp (Substrate)

Registered Products (1)

Brand	Form / strength	Pack	Agent	Citizen (JOD)
Saflutan 15mcg/ml Eye Drops	Ophthalmic Solution 15 mcg/ml	0.3 ml	Adatco Drug Store	12.940