ChemicalBook--->CAS DataBase List--->54276-17-4

54276-17-4

54276-17-4 Structure

54276-17-4 Structure
IdentificationBack Directory
[Name]

Travoprost Acid
[CAS]

54276-17-4
[Synonyms]

AL 5848
Travoprost Acid
Travoprost Acid-d4
[3H]-Travoprost acid
Travoprost free acid
Travoprost impurity E
Ttravoprost free acid
Fluprostenol Travoprost acid
Travoprost Impurity 12(Fluprostenol)
16-(M-TrifluoroMethylphenoxy)-17,18,19,20-tetranorprostaglandin F2α
(Z)-7-((1R,2R,3R,5S)-3,5-Dihydroxy-2-((R,E)-3-hydroxy-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)cyclopentyl)hept-5-enoic 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
(5Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-5-heptenoic acid
5-Heptenoic acid, 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]cyclopentyl]-, (5Z)-
Travoprost Related Compound A (1673012)Q: What is Travoprost Related Compound A (1673012) Q: What is the CAS Number of Travoprost Related Compound A (1673012)
Travoprost Acid/Travoprost USP Related Compound A/(5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic Acid
[Molecular Formula]

C23H29F3O6
[MDL Number]

MFCD00210955
[MOL File]

54276-17-4.mol
[Molecular Weight]

458.47
Chemical PropertiesBack Directory
[Boiling point ]

608.0±55.0 °C(Predicted)
[density ]

1.335±0.06 g/cm3(Predicted)
[storage temp. ]

-20°C Freezer
[solubility ]

DMSO (Slightly), Methanol (Slightly, Sonicated), Dichloromethane, Acetonitrile
[form ]

Solid
[pka]

4.76±0.10(Predicted)
[color ]

Colourless to Pale Yellow Oil
[InChIKey]

WWSWYXNVCBLWNZ-QIZQQNKQSA-N
[SMILES]

C(O)(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1
Safety DataBack Directory
[Symbol(GHS) ]

Health Hazard (GHS08)Skull and Crossbones (GHS06)
GHS08,GHS06
[Signal word ]

Danger
[Hazard statements ]

H372-H370-H300+H310+H330
[Precautionary statements ]

P260-P264-P270-P307+P311-P321-P405-P501-P260-P264-P270-P314-P501
[HS Code ]

2937500000
Hazard InformationBack Directory
[Chemical Properties]

Colorless to light yellow Liquid
[Uses]

A metabolically stable analog of Prostaglandin F2α (P838625) with potent FP receptor agonist activity. An impurity of Travoprost (T715600).
[Uses]

Fluprostenol is a metabolically stable analog of PGF2α with potent FP receptor agonist activity. Fluprostenol is the optically active enantiomer of fluprostenol and would be expected to have twice the potency as the racemic mixture. Fluprostenol inhibits PGF2α binding to human and rat FP receptors with IC50 values of 3.5 and 7.5 nM, respectively. It is a much more potent luteolytic agent than PGF2α in rats with a minimum fully effective dose of 270 μg/kg to terminate pregnancy. It is also an effective inhibitor of rat adipose precursor differentiation in primary cultures with an IC50 of 3-10 x 10?11 M.[Cayman Chemical]
[Definition]

ChEBI:Fluprostenol is an organofluorine compound that is racemic prostaglandin F2alpha in which the pentyl group is replaced by a 3-(trifluoromethyl)phenoxymethyl group. A synthetic analogue of prostaglandin F2alpha, ophthalmic solutions of its isopropyl ester prodrug, travoprost, are used as a topical medication for controlling the progression of open-angle glaucoma and ocular hypertension, by reducing intraocular pressure. The isopropyl ester group of travoprost is hydrolysed to the biologically active free acid by esterases in the cornea. It has a role as an antiglaucoma drug, an antihypertensive agent, a prostaglandin receptor agonist, a female contraceptive drug and an abortifacient. It is a prostaglandins Falpha, a hydroxy monocarboxylic acid and a member of (trifluoromethyl)benzenes.
[Mechanism of action]

(+)-Fluprostenol has an intraocular hypotensive effect and has the potential to treat glaucoma and ocular hypertension. Fluprostenol blocks the fibrotic effects of connective tissue growth factor (CTGF) on human trabecular meshwork (TM) cells and increases the activity of MMP2. Both effects have the potential to attenuate CTGF-mediated TM extracellular matrix increases and the resulting effects on TM outflow resistance in patients with primary open-angle glaucoma (POAG).[1]
[storage]

Store at -20°C
[References]

[1] RUDOLF FUCHSHOFER. The prostaglandin f2α analog fluprostenol attenuates the fibrotic effects of connective tissue growth factor on human trabecular meshwork cells.[J]. Journal of Ocular Pharmacology and Therapeutics, 2014, 30 2-3: 237-245. DOI:10.1089/jop.2013.0205.
Spectrum DetailBack Directory
[Spectrum Detail]

Travoprost Acid(54276-17-4)1HNMR
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