57968-83-9

Basic information

• Product Name: 5-TRANS FLUPROSTENOL
• Synonyms: 5-TRANS FLUPROSTENOL;9ALPHA,11ALPHA,15R-TRIHYDROXY-16-(3-(TRIFLUOROMETHYL)PHENOXY)-17-18,19,20-TETRANOR-PROSTA-5E,13E-DIEN-1-OIC ACID;WWSWYXNVCBLWNZ-BDFMIYKPSA-N
• CAS NO: 57968-83-9
• Molecular Formula: C₂₃H₂₉F₃O₆
• Molecular Weight: 458.47
• Mol File: 57968-83-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-TRANS FLUPROSTENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 5-TRANS FLUPROSTENOL(57968-83-9)
• EPA Substance Registry System: 5-TRANS FLUPROSTENOL(57968-83-9)

Safety Data

• Hazardous Substances Data: 57968-83-9(Hazardous Substances Data)

Usage

General Description

5-TRANS FLUPROSTENOL is a synthetic analog of prostaglandin F2α that is used in the treatment of glaucoma. It works by reducing intraocular pressure, making it an effective medication for managing this condition. Its chemical structure includes a trans double bond at the C-5 position, which is important for its pharmacological activity. 5-TRANS FLUPROSTENOL is typically administered as an eye drop and is well-tolerated by most patients. It is considered to be a valuable option for individuals with glaucoma and is commonly prescribed by healthcare professionals to help manage this condition.

Relevant articles and documents

A novel convergent synthesis of the potent antiglaucoma agent travoprost

The 16-(3-trifluoromethyl)phenoxy PGF2α analogue travoprost (8a) has potent topical ocular activity. A novel convergent synthesis of 13,14-en-15-ol PGF2α analogues was developed employing Julia-Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone (5Z)-(+)-15 with a new enantiomerically pure aldehyde ω-chain synthon (S)-(-)-16a. Subsequent hydrolysis of protecting groups and final esterification of fluprostenol (7a) yielded travoprost (8a). The main advantages are the preparation of high purity travoprost (8a) and the application of comparatively cheap reagents. The novel convergent strategy allows the synthesis of a whole series of 13,14-en-15-ol PGF2α analogues from a common and structurally advanced prostaglandin intermediate 15. The preparation and identification of two synthetic impurities, 15-epi isomer (8b) of travoprost and a new prostaglandin related ester (5Z)-(+)-18, are also described.

Synthesis of (±) travoprost and its analogs

A new synthetic approach for the antiglaucoma agent, travoprost (1) has been developed in four steps from key intermediate (2). Key transformations include Horner-Wadsworth-Emmons reaction and separation of diastereomers to obtain (±) travoprost (1) and its analogs.