Travoprost
[CAS# 157283-68-6]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Travoprost
• Synonyms: Propan-2-yl (E)-7-[(1R,2S,3R,5S)-3,5-dihydroxy-2-[(E)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]hept-5-enoate
• Molecular Formula: C₂₆H₃₅F₃O₆
• Molecular Weight: 500.55
• CAS Registry Number: 157283-68-6
• EC Number: 682-028-9
• SMILES: CC(C)OC(=O)CCC/C=CC[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](COC2=CC=CC(=C2)C(F)(F)F)O)O)O

Properties

• Solubility: 40 mM (DMSO), soluble (ethanol)

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H302-H315-H319-H335-H361-H362
• Safety Statements: P203-P260-P261-P263-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Lact.	-	H362
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	1B	H360
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovery and Applications

Travoprost is a synthetic prostaglandin analog used primarily for the treatment of glaucoma and ocular hypertension. Its discovery was part of ongoing research to improve intraocular pressure (IOP)-lowering agents by modifying natural prostaglandins to enhance their therapeutic efficacy and minimize side effects. Prostaglandins are lipid compounds that have various roles in the body, including the regulation of IOP in the eye. Travoprost, like other prostaglandin analogs, works by increasing the outflow of aqueous humor from the eye, thereby reducing elevated IOP.

The development of Travoprost stemmed from the need to address limitations observed in earlier prostaglandin-based treatments, such as latanoprost. In the late 1990s, researchers modified the structure of natural prostaglandins to increase receptor selectivity and stability. Travoprost was synthesized by incorporating specific chemical modifications that improved its potency and duration of action in reducing IOP. It is a prodrug, meaning it becomes active once metabolized in the eye, where it is converted into its biologically active form, travoprost acid.

Travoprost is widely used in ophthalmology to manage open-angle glaucoma and ocular hypertension, conditions characterized by elevated pressure within the eye that can lead to optic nerve damage and vision loss if untreated. The drug is administered as eye drops and has been shown to be effective in patients who do not respond well to other IOP-lowering medications. Travoprost is often preferred due to its relatively favorable side-effect profile, though common side effects may include eye redness, eyelash growth, and changes in iris pigmentation.

In addition to its clinical applications, Travoprost has also been studied in various research contexts to better understand the mechanisms of aqueous humor dynamics and to develop future therapeutic agents for glaucoma. Its development has marked a significant advancement in the field of ophthalmic prostaglandin analogs, offering a potent and long-lasting option for glaucoma management.

References

2024. Long-Term Safety and Efficacy Evaluation of Travoprost Intracameral Implant Based on Pooled Analyses from Two Phase III Trials. Drugs. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11512891

2024. Sustained Release Therapies with the Prostaglandin Analogues Intracameral Implants. Ophthalmology and Therapy. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11178720

2001. Comparison of Topical Travoprost Eye Drops Given Once Daily and Timolol 0.5% Given Twice Daily in Patients with Open-Angle Glaucoma or Ocular Hypertension. Journal of Glaucoma. URL: https://pubmed.ncbi.nlm.nih.gov/11711841