54276-17-4

Basic information

• Product Name: Travoprost Acid
• Synonyms: Travoprost Acid;(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoroMethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic Acid;[1R-[1α(Z),2β(1E,3R*),3α,5α]]-7-[3,5-Dihydroxy-2-[3-hydroxy-4-[3-(trifluoroMethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic Acid;16-(M-TrifluoroMethylphenoxy)-17,18,19,20-tetranorprostaglandin F2α;AL 5848
• CAS NO: 54276-17-4
• Molecular Formula: C₂₃H₂₉F₃O₆
• Molecular Weight: 458.4679696
• Product Categories: Agonists;Chiral Reagents;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 54276-17-4.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 608.0±55.0 °C(Predicted)
• Appearance: /
• Density: 1.335±0.06 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Sonicated), Dichloromethane, Acetonitrile
• PKA: 4.76±0.10(Predicted)
• CAS DataBase Reference: Travoprost Acid(CAS DataBase Reference)
• NIST Chemistry Reference: Travoprost Acid(54276-17-4)
• EPA Substance Registry System: Travoprost Acid(54276-17-4)

Safety Data

• Hazardous Substances Data: 54276-17-4(Hazardous Substances Data)

Usage

Description

Travoprost Acid, also known as Travoprost, is a metabolically stable analog of Prostaglandin F2α (P838625) with potent FP receptor agonist activity. It is an impurity of Travoprost (T715600) and is derived from the optically active enantiomer of fluprostenol, which is a metabolically stable analog of PGF2α. Travoprost Acid possesses potent biological activities and is a promising pharmaceutical candidate for various applications.

Uses

Used in Pharmaceutical Industry:
Travoprost Acid is used as a pharmaceutical agent for its potent FP receptor agonist activity. It modulates the biological processes by binding to the FP receptors, which can be utilized in the treatment of various medical conditions.
Used in Ophthalmology:
Travoprost Acid is used as a glaucoma treatment agent for its ability to reduce intraocular pressure. It is effective in managing glaucoma by improving the outflow of aqueous humor, thus providing relief to patients suffering from this eye condition.
Used in Obstetrics:
Travoprost Acid is used as a luteolytic agent for its potent activity in terminating pregnancy. It is a much more potent luteolytic agent than PGF2α in rats, with a minimum fully effective dose of 270 μg/kg.
Used in Cell Biology Research:
Travoprost Acid is used as an inhibitor of rat adipose precursor differentiation in primary cultures. It effectively inhibits the differentiation process with an IC50 of 3-10 x 10^(-11) M, making it a valuable tool for studying adipose tissue development and related cellular processes.

Upstream product

• 1204185-88-5 (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-2,5-diol 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 54142-64-2 [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2H-cyclopenta[b]furan-5-yl ester 
• 114488-91-4 [1,1'-biphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-2-oxo-2H-cyclopenta[b]furan-5-yl ester 
• 87422-39-7 (3aR,6aS)-3,3-dichloro-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one 
• 5307-99-3 (+/-)-7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 98-17-9 3-Trifluoromethylphenol 
• 340181-93-3 travoprost 
• 955005-75-1 2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)-phenoxy]-1-butenyl]cyclopentyl]-5-heptenoate 

Downstream Products

• 340181-93-3 travoprost 
• 73275-76-0 (Z)-methyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoate 
• 1224444-58-9 travoprost L-homoarginine salt 
• 1224443-24-6 arginyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-enyl)cyclopentyl)hept-5-enoate 

Relevant articles and documents

A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis

Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.

HETERODIMER COMPOSITIONS AND METHODS FOR THE TREATMENT OF OCULAR DISORDERS

Described herein are processable compositions comprising at least one moiety that is processable in its free form. Also described herein are compositions and methods for the treatment of ocular diseases or disorders including glaucoma, blepharitis, ocular inflammation, diabetic macular edema, posterior inflammation, anterior inflammation, macular degeneration (e.g., wet macular degeneration (AMD) or dry AMD), post-cataract surgery, and retinal vein occlusion. Said compositions and methods comprise steroids and prostaglandins which demonstrate anti-inflammatory activity, intraocular pressure (IOP) lowering, and/or other desirable activities. Injection of said compositions in the eye provides therapeutic benefit to patients suffering from ocular disorders.

PROCESS FOR PREPARATION OF PROSTAGLANDIN F2 ALPHA ANALOGUES

A convergent synthesis of the prostaglandin F2α analogues, travoprost and bimatoprost, was developed employing Julia-Lythgoe olefination of the structurally advanced phenylsulfone with an enantiomerically pure aldehyde ω-chain synthon. The novel convergent strategy allows the synthesis of a whole series of prostaglandin analogues of high purity from a common and structurally advanced prostaglandin intermediate.