Latanoprost
[CAS# 130209-82-4]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Latanoprost
• Synonyms: Propan-2-yl 7-[3,5-dihydroxy-2-(3-hydroxy-5-phenyl-pentyl)-cyclopentyl]hept-5-enoate
• Molecular Formula: C₂₆H₄₀O₅
• Molecular Weight: 432.60
• CAS Registry Number: 130209-82-4
• EC Number: 634-172-9
• SMILES: CC(C)OC(=O)CCC/C=CC[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O

Properties

• Solubility: Soluble 50 mM (DMSO), 50 mM (ethanol)

Safety Data

• Hazard Symbols: GHS06;GHS08 Danger
• Risk Statements: H300-H301-H362
• Safety Statements: P203-P264-P270-P280-P301+P316-P318-P321-P330-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	1	H300
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	3	H301
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	1A	H360
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

Latanoprost is a synthetic prostaglandin analog widely used in ophthalmology to manage conditions such as glaucoma and ocular hypertension. Its primary mechanism of action involves increasing the outflow of aqueous humor from the eye, thus lowering intraocular pressure (IOP). The compound was discovered in the late 1980s by Dr. Johan Stjernschantz and his team at the University of Umeå in Sweden, in collaboration with Pharmacia Corporation. Their research was driven by the need to develop a more effective and better-tolerated treatment for glaucoma, a condition that can lead to irreversible blindness if untreated.

The discovery of latanoprost was rooted in earlier studies on prostaglandin F2α, which had been shown to reduce intraocular pressure but was associated with significant side effects, such as inflammation and irritation. By modifying the chemical structure of prostaglandins, Stjernschantz and his team were able to create a more stable compound that retained the IOP-lowering effect without the undesirable side effects. Latanoprost was specifically designed to be a prodrug, meaning it becomes activated only after it is absorbed by the tissues of the eye, thereby enhancing its therapeutic profile and reducing systemic exposure.

Latanoprost is marketed under the trade name Xalatan and has become one of the most widely prescribed medications for glaucoma. It is administered as an eye drop, typically once a day, making it convenient for long-term use. Its efficacy in reducing IOP, coupled with its relatively mild side effect profile, has made it a cornerstone of glaucoma treatment. Common side effects include mild eye irritation and changes in the pigmentation of the iris, which are generally well tolerated by most patients.

In addition to its use in glaucoma, latanoprost has been investigated for potential applications in other areas of ophthalmology, such as the treatment of retinal diseases. Research into combination therapies involving latanoprost and other IOP-lowering agents has also been pursued, with the goal of improving patient outcomes in cases where monotherapy is insufficient.

Latanoprost’s discovery marked a significant advancement in glaucoma therapy, offering a more effective and patient-friendly alternative to older treatments. Its continued use and development demonstrate its importance in the management of ocular diseases, ensuring better quality of life for individuals affected by glaucoma and ocular hypertension.

References

2000. Substituting latanoprost (Xalatan) for isopropyl unoprostone (Rescula) in monotherapy and combination therapy. Acta Ophthalmologica Scandinavica, 78(5).
DOI: 10.1034/j.1600-0420.2000.078005604.x

2003. Update on prostaglandin analogs. Current Opinion in Ophthalmology, 14(2).
DOI: 10.1097/00055735-200304000-00001

2005. Efficacy and Safety of Latanoprost for Glaucoma Treatment: A Three-Month Multicentric Study in India. Indian Journal of Ophthalmology, 53(1).
DOI: 10.4103/0301-4738.15281