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

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

Uses

Used in Ophthalmology:
Tafluprost ethyl amide is used as a therapeutic agent for the treatment of glaucoma and ocular hypertension. It functions by increasing the outflow of aqueous humor, thereby reducing intraocular pressure, which is crucial in managing these conditions and preventing further damage to the eye.
Used in Pharmaceutical Research and Development:
Tafluprost ethyl amide is utilized in the research and development of new ophthalmic medications. Its potential applications in treating various ophthalmic conditions make it a valuable compound for pharmaceutical companies and researchers seeking to innovate and improve treatment options for eye diseases.
Used in Drug Formulation:
As a derivative of tafluprost, Tafluprost ethyl amide is used in the formulation of new drug products aimed at enhancing the bioavailability and effectiveness of existing prostaglandin analogs. This can lead to improved patient outcomes and more efficient treatments for glaucoma and related eye conditions.

Upstream product

• 209860-88-8 AFP-172 
• 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 

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.