1185851-52-8

Basic information

• Product Name: Tafluprost ethyl amide
• Synonyms: Tafluprost ethyl amide;Dechloro dihydroxy difluoro ethylcloprostenolamide;(Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]-N-ethylhept-5-enamide
• CAS NO: 1185851-52-8
• Molecular Formula: C24H33F2NO4
• Molecular Weight: 437.5199264
• Mol File: 1185851-52-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 609.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.191±0.06 g/cm3(Predicted)
• PKA: 14.48±0.70(Predicted)
• CAS DataBase Reference: Tafluprost ethyl amide(CAS DataBase Reference)
• NIST Chemistry Reference: Tafluprost ethyl amide(1185851-52-8)
• EPA Substance Registry System: Tafluprost ethyl amide(1185851-52-8)

Safety Data

• Hazardous Substances Data: 1185851-52-8(Hazardous Substances Data)

Usage

General Description

Tafluprost ethyl amide is a chemical compound that belongs to the class of prostaglandin analogs, which are commonly used in the treatment of glaucoma and ocular hypertension. It is a derivative of the medication tafluprost, which is a prostaglandin F2alpha analog. Tafluprost ethyl amide is designed to improve the bioavailability and efficacy of tafluprost. It works by reducing intraocular pressure by increasing the outflow of aqueous humor from the eye. This chemical compound is currently being investigated for its potential use in the treatment of various ophthalmic conditions, and is of interest to researchers and pharmaceutical companies for its potential therapeutic applications.

Upstream product

• 913258-17-0 1-<(Z)-6-{(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis(triethylsiloxy)cyclopentyl}hex-4-enyl>-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 
• 538-43-2 3-phenoxy-1,2-propanediol 
• 53379-98-9 2,2-dimethyl-4-phenoxymethyl-[1,3]dioxolane 
• 108-95-2 phenol 
• 75-04-7 ethylamine 
• 209860-87-7 tafluprost 
• 209860-88-8 AFP-172 

Relevant articles and documents

A novel convergent synthesis of the potent antiglaucoma agent tafluprost

Tafluprost (AFP-168, 5) is a unique 15-deoxy-15,15-difluoro-16-phenoxy prostaglandin F2α (PGF2α) analog used as an efficacious ocular hypotensive agent in the treatment of glaucoma and ocular hypertension, as monotherapy, or as adjunctive therapy to β-blockers. A novel convergent synthesis of 5 was developed employing Julia-Lythgoe olefination of the structurally advanced prostaglandin phenylsulfone 16, also successfully applied for manufacturing of pharmaceutical grade latanoprost (2), travoprost (3) and bimatoprost (4), with an aldehyde !-chain synthon 17. The use of the same prostaglandin phenylsulfone 16, as a starting material in parallel syntheses of all commercially available antiglaucoma PGF2α analogs 2-5, significantly reduces manufacturing costs resulting from its synthesis on an industrial scale and development of technological documentation. Another key aspect of the route developed is deoxydifluorination of a trans-13,14-en-15-one 30 with Deoxo-Fluor. Subsequent hydrolysis of protecting groups and final esterification of acid 6 yielded tafluprost (5). The main advantages are the preparation of high purity tafluprost (5) and the application of comparatively cheap reagents. The preparation and identification of two other tafluprost acid derivatives, tafluprost methyl ester (32) and tafluprost ethyl amide (33), are also described.