(+)-Fluprostenol Chemical Properties

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 Information

HS Code 

2937500000

(+)-Fluprostenol Usage And Synthesis

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]

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.

(+)-Fluprostenol(54276-17-4)Related Product Information

• Tafluprost
• Iodoethane
• Ethyl bromoacetate
• 15(S)-Fluprostenol isopropyl ester
• Travoprost
• 15-KETO FLUPROSTENOL
• 5,6-trans Travoprost
• 3-Trifluoromethylphenol
• 15-Keto Travoprost
• 9-keto Fluprostenol isopropyl ester
• 9-KETO FLUPROSTENOL
• (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]cyclopentyl]-N-(1,3-dihydroxypropan-2-yl)hept-5-enamide
• 11-KETO FLUPROSTENOL