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Key Documents

F8549

Sigma-Aldrich

Fluprostenol

10 mg/mL in ethanol, 98%

Synonym(s):

(±)-16-(3-Trifluoromethylphenoxy)tetranorprostaglandin F

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About This Item

Empirical Formula (Hill Notation):
C23H29F3O6
CAS Number:
Molecular Weight:
458.47
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

98%

concentration

10 mg/mL in ethanol

storage temp.

−20°C

SMILES string

O[C@H](COc1cccc(c1)C(F)(F)F)\C=C\[C@@H]2[C@@H](O)C[C@@H](O)[C@H]2C\C=C/CCCC(O)=O

InChI

1S/C23H29F3O6/c24-23(25,26)15-6-5-7-17(12-15)32-14-16(27)10-11-19-18(20(28)13-21(19)29)8-3-1-2-4-9-22(30)31/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m0/s1

InChI key

WWSWYXNVCBLWNZ-CHPNCWRZSA-N

Application

Fluprostenol has been used as a prostaglandin F (FP) receptor agonist to study its effects on osteoclast development. It has also been used as a prostaglandin F2α (PGF2α) receptor agonist to study its effects on mitogen-activated protein kinase (MAPK) signaling in rat aorta.

Biochem/physiol Actions

Fluprostenol is a selective prostaglandin F2-α (PGF2α) receptor or prostaglandin F (FP) receptor agonist.

pictograms

FlameExclamation mark

signalword

Danger

hcodes

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Tara L Aghaloo et al.
Journal of periodontology, 77(1), 21-30 (2006-04-04)
Parathyroid hormone (PTH) regulates osteoblast function by binding to the PTH receptor 1 (PTHR1) to activate downstream signaling to induce expression of primary response genes (PRGs), which affect various aspects of the osteoblast phenotype. We previously identified PTH-induced PRGs in
Potent luteolytic agents related to prostaglandin F2alpha.
M Dukes et al.
Nature, 250(464), 330-331 (1974-07-26)
Maria Giovanna Sabbieti et al.
Cell and tissue research, 319(2), 267-278 (2005-01-18)
We have previously reported that prostaglandin F(2alpha) (PGF(2alpha)) and its selective agonist fluprostenol increase basic fibroblast growth factor (FGF-2) mRNA and protein production in osteoblastic Py1a cells. The present report extends our previous studies by showing that Py1a cells express
M P Carrasco et al.
The Journal of clinical endocrinology and metabolism, 81(6), 2104-2110 (1996-06-01)
The objective of this study was to investigate the mechanism of action of PGF2 alpha in cultured human myometrial cells. We measured the effects of PGF2 alpha and fluprostenol, a selective PGF2 alpha receptor (FP receptor) agonist, on phospholipase C(PLC)
Toshiyuki Ueno et al.
The FEBS journal, 278(16), 2901-2912 (2011-06-15)
Prostaglandin (PG) F(2α) suppresses adipocyte differentiation by inhibiting the function of peroxisome proliferator-activated receptor γ. In this study, we identified a novel suppression mechanism, operating in the early phase of adipogenesis, that increased the production of anti-adipogenic PGF(2α) and PGE(2)

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