Basic information Safety Supplier Related

(+)-Fluprostenol

Basic information Safety Supplier Related

(+)-Fluprostenol Basic information

Product Name:
(+)-Fluprostenol
Synonyms:
  • (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
  • Travoprost Acid
  • Ttravoprost free acid
  • Travoprost Acid-d4
  • [3H]-Travoprost acid
CAS:
54276-17-4
MF:
C23H29F3O6
MW:
458.47
Product Categories:
  • API
  • Agonists
  • Chiral Reagents
  • Impurities
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
54276-17-4.mol
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(+)-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
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Safety Information

HS Code 
2937500000
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(+)-Fluprostenol Usage And Synthesis

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.

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