Tafluprost
[CAS# 209860-87-7]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Tafluprost
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-Difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid 1-methylethyl ester
• Molecular Formula: C₂₅H₃₄F₂O₅
• Molecular Weight: 452.53
• CAS Registry Number: 209860-87-7
• EC Number: 682-458-7
• SMILES: CC(C)OC(=O)CCC/C=CC[C@H]1[C@H](C[C@H]([C@@H]1/C=C/C(COC2=CC=CC=C2)(F)F)O)O

Properties

• Density: 1.186
• Solubility: 10 mM (DMSO)

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H302-H319-H360-H372-H413
• Safety Statements: P203-P260-P264-P264+P265-P270-P273-P280-P301+P317-P305+P351+P338-P308+P316-P318-P319-P321-P330-P337+P317-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	1B	H360
Specific target organ toxicity - single exposure	STOT SE	1	H370
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - repeated exposure	STOT RE	2	H373

Discovery and Applications

Tafluprost is a synthetic prostaglandin analog primarily used in the treatment of ocular hypertension and open-angle glaucoma. Its development was driven by the need for more effective and safer therapies to reduce intraocular pressure (IOP), a key factor in preventing damage to the optic nerve in glaucoma patients. Tafluprost was first synthesized by Santen Pharmaceutical Co., Ltd. in Japan as part of their research into prostaglandin F2α analogs, which are known to lower IOP by increasing the outflow of aqueous humor in the eye.

The chemical structure of tafluprost includes a fluorine atom, which enhances its biological stability and potency compared to other prostaglandin analogs. It is marketed under the trade name "Zioptan" in several countries. Unlike other prostaglandin-based drugs for glaucoma, tafluprost is notable for being preservative-free, reducing the risk of adverse effects such as ocular surface disease that can arise from preservatives like benzalkonium chloride in other formulations.

Tafluprost works by binding to prostaglandin FP receptors in the ciliary body of the eye, leading to an increase in uveoscleral outflow, which ultimately reduces IOP. Clinical trials have demonstrated its effectiveness in lowering IOP by up to 30%, making it a competitive treatment option in the prostaglandin analog drug class. Its unique fluorinated structure also contributes to a favorable safety profile with fewer side effects compared to its predecessors.

In addition to treating glaucoma and ocular hypertension, tafluprost has been studied for its potential in combination therapies. For instance, combining tafluprost with other agents like beta-blockers or carbonic anhydrase inhibitors can offer enhanced IOP-lowering effects for patients who require multiple drugs to manage their condition effectively.

Tafluprost continues to be an important treatment option for glaucoma patients worldwide, contributing significantly to the prevention of vision loss associated with elevated IOP. Its preservative-free formulation offers a notable advantage for individuals with sensitive eyes, further expanding its applicability in clinical practice.

References

2004. Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Experimental Eye Research.
DOI: 10.1016/j.exer.2003.12.007

2024. Real-Life Study on the Efficacy and Tolerance of a Preservative-Free Surfactant-Free Latanoprost Eye Drop in Patients with Glaucoma. Ophthalmology and Therapy.
DOI: 10.1007/s40123-024-01013-x

2024. Preservative-Free Fixed Combination of Tafluprost 0.0015% and Timolol 0.5% for Treatment-Naive Patients with Open-Angle Glaucoma. Korean journal of ophthalmology: KJO.
DOI: 10.3341/kjo.2024.0021