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(+)-Fluprostenol

CAS No.
54276-17-4
Chemical 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;AL 5848;Travoprost 2;Travoprost Acid;(+)-Fluprostenol;Travoprost Acid-d4;[3H]-Travoprost acid;Travoprost free acid;Ttravoprost free acid;Travoprost impurity E
CBNumber:
CB02551360
Molecular Formula:
C23H29F3O6
Molecular Weight:
458.47
MDL Number:
MFCD00210955
MOL File:
54276-17-4.mol
Last updated:2023-09-04 15:51:00

(+)-Fluprostenol 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
FDA UNII MEH3MCE8X1

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
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
NFPA 704
3
3 0

(+)-Fluprostenol price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 16768 Fluprostenol ≥95% 54276-17-4 1mg $64 2024-03-01 Buy
Cayman Chemical 16768 Fluprostenol ≥95% 54276-17-4 5mg $280 2024-03-01 Buy
Cayman Chemical 16768 Fluprostenol ≥95% 54276-17-4 10mg $497 2024-03-01 Buy
Cayman Chemical 16768 Fluprostenol ≥95% 54276-17-4 25mg $1084 2024-03-01 Buy
TRC T715620 TravoprostAcid 54276-17-4 25mg $895 2021-12-16 Buy
Product number Packaging Price Buy
16768 1mg $64 Buy
16768 5mg $280 Buy
16768 10mg $497 Buy
16768 25mg $1084 Buy
T715620 25mg $895 Buy

(+)-Fluprostenol Chemical Properties,Uses,Production

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]

Uses

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

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.

1204185-88-5
17814-85-6
54276-17-4
Synthesis of (+)-Fluprostenol from 2H-Cyclopenta[b]furan-2,5-diol, hexahydro-4-[(1E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]-1-buten-1-yl]-, (3aR,4R,5R,6aS)- and (4-Carboxybutyl)triphenylphosphonium bromide
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(+)-Fluprostenol Spectrum

[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 Travoprost Impurity 12(Fluprostenol) (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 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 Fluprostenol Travoprost 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 free acid (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 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 impurity E (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxy-4-[3-(trifluoroMethyl)phenoxy]-1-butenyl]cyclopentyl]-5-heptenoic Acid Travoprost 2 PTGER2,Oviductal glycoprotein 1,(+) Fluprostenol,inhibit,(+)Fluprostenol,OVGP1,Inhibitor,(+)-Fluprostenol (Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(E,3R)-3-hydroxy- 4-[3-(trifluoromethyl) phenoxy] but-1-enyl] cyclopentyl]hept-5-enoic acid (+)-Fluprostenol 54276-17-4 Agonists Chiral Reagents Impurities Intermediates & Fine Chemicals Pharmaceuticals API