Latanoprost

• CAS: 130209-82-4
• Catalog Number: ACM130209824-1
• Category: Main Products
• Molecular Weight: 432.59
• Molecular Formula: C26H40O5
• Description: Latanoprost eye solution is a medication administered into the eyes to control the progression of glaucoma or ocular hypertension by reducing intraocular pressure (IOP). It is a prostaglandin analogue (more specifically an analogue of prostaglandin F2α) that lowers the pressure by increasing the outflow of aqueous fluid from the eyes through the uveoscleral tract. Latanoprost is an isopropyl ester prodrug, meaning it is inactive until it is hydrolyzed by esterases in the cornea to the biologically active acid.Latanoprost was invented by Johan W. Stjernschantz and Bahram Resul, employees of the Pharmacia Corporation of Uppsala, Sweden. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system. It is also known by the brand name of Xalatan manufactured by Pfizer. Annual sales are approximately $1.6 billion. The patent for latanoprost expired in March 2011, and at least one generic version is now widely available in the U.S.
• Synonyms: Isopropyl (5Z,9Α,11Α,15R)-9,11,15-Trihydroxy-17-Phenyl-18,19,20-Trinor-Prost-5-En-1-Oate
• Canonical SMILES: CC(C)OC(=O)CCC/C=C\\C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@H](CCC2=CC=CC=C2)O)O)O
• Boiling Point: 583.8 °C at 760 mmHg (Predicted)
• Flash Point: 188.3ºC
• Density: 1.093 g/cm³
• Appearance: Oil
• HS Code: 2937500000
• LogP: 4.18640
• PSA: 86.99
• Refractive Index: 1.537
• Storage Conditions: -20ºC
• WGK Germany: 3

Case Study

Evaluation of Latanoprost for the Treatment of Open-Angle Glaucoma

Garway-Heath, David F., et al. The Lancet, 2015, 385(9975), 1295-1304.

This work evaluated the preservation of visual acuity in patients treated with latanoprost compared with those treated with placebo. This randomized, placebo-controlled trial showed that the use of an ocular hypotensive medication can preserve visual fields in patients with open-angle glaucoma.
Evaluation methods and results
· In this study, patients with newly diagnosed open-angle glaucoma were enrolled. The patients were randomly assigned to either receive latanoprost 0.005% eye drops or a placebo, with the allocation determined by a website-generated randomization schedule. The eye drops were administered once a day to both eyes from identical bottles. The primary outcome was the time to visual field deterioration within 24 months. The trial was triple-masked, meaning both the patients, investigators, and outcome assessors were unaware of the treatment assignment.
· The 516 subjects were divided into a latanoprost group and a control group. The baseline mean intraocular pressure was measured at 19.6 mm Hg with a standard deviation of 4.6 for the latanoprost group, and 20.1 mm Hg with a standard deviation of 4.8 for the control group. At 24 months, the mean reduction in intraocular pressure was 3·8 mm Hg (4.0) in 231 patients in the latanoprost group and 0·9 mm Hg (3.8) in 230 patients in the placebo group. Visual field preservation was significantly longer in the latanoprost group compared to the placebo group with an adjusted hazard ratio (HR) of 0·44 (95% CI 0.28-0.69; p=0.0003).

Evaluation of the Efficacy of Latanoprost in the Treatment for Vitiligo

Anbar, Tag S., et al. International journal of dermatology, 2015, 54(5), 587-593.

Latanoprost (LT) is a prostaglandin F2alpha (PGF2α) analog that has been found to induce skin pigmentation in guinea pigs, in addition to known side effects of periocular and iris pigmentation. This study evaluated the efficacy of topical LT in inducing skin repigmentation in patients with vitiligo and compared its efficacy with narrow-band ultraviolet (UV) B (NB-UVB).
Experimental methods and results
· The 22 patients were divided into three groups: group I evaluated LT versus placebo; group II evaluated LT versus NB-UVB; and group III evaluated the combination of the two treatments. The response to the treatments was assessed by capturing photographic records of the treated lesions every two weeks. After three months, the degree and extent of repigmentation were evaluated. A follow-up assessment was conducted six months after the trial ended to check for the persistence of pigmentation, any recurrence, or the development of side effects.
· LT was found to be superior to placebo and similar in effectiveness to NB-UVB in promoting skin repigmentation. The combination of LT with NB-UVB further enhanced this effect. The study emphasized several advantages of using LT in treating vitiligo, such as its easy self-application, availability, affordability, effectiveness in treating periocular vitiligo without any observed side effects, and the optional but beneficial combination with phototherapy for an improved response.

Custom Q&A

What is the molecular formula of latanoprost?

The molecular formula of latanoprost is C26H40O5.

What is the molecular weight of latanoprost?

The molecular weight of latanoprost is 432.6 g/mol.

What is the role of latanoprost?

Latanoprost has a role as an antiglaucoma drug, an antihypertensive agent, an EC 4.2.1.1 (carbonic anhydrase) inhibitor and a prodrug.

When was latanoprost created and modified?

Latanoprost was created on 2005-12-16 and modified on 2023-12-30.

What is the IUPAC name of latanoprost?

The IUPAC name of latanoprost is propan-2-yl (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate.

How is latanoprost administered?

Latanoprost can be administered once a day.

What is the InChIKey of latanoprost?

The InChIKey of latanoprost is GGXICVAJURFBLW-CEYXHVGTSA-N.

What is the Canonical SMILES of latanoprost?

The Canonical SMILES of latanoprost is CC(C)OC(=O)CCCC=CCC1C(CC(C1CCC(CCC2=CC=CC=C2)O)O)O.

What is the CAS number of latanoprost?

The CAS number of latanoprost is 130209-82-4.

What class of drug does latanoprost belong to?

Latanoprost belongs to the Prostaglandin Analog drug class.