A potent FP receptor agonist
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Labeled Version(s)
316767Fluprostenol-d4
Pro-drug Form(s)
16769Fluprostenol isopropyl ester
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Fluprostenol

Item No. 16768

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15R-trihydroxy-16-(3-(trifluoromethyl)phenoxy)-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-oic acid
CAS Number
54276-17-4
Synonyms
  • 16-m-trifluoromethylphenoxy tetranor Prostaglandin F2α
Molecular Formula
C23H29F3O6
Formula Weight
458.5
Purity
≥95%
Formulation
A 10 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mLDMSO: >100 mg/mLEthanol: >100 mg/mLPBS (pH 7.2): >16 mg/mL
λmax
222, 280 nm
SMILES
O[C@@H]1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)COC2=CC=CC(C(F)(F)F)=C2)[C@H](O)C1
InChi Code
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-/m1/s1
InChi Key
WWSWYXNVCBLWNZ-QIZQQNKQSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Fluprostenol is a metabolically stable analog of PGF2α with potent FP receptor agonist activity.1,2 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.1,2 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.3 It is also an effective inhibitor of rat adipose precursor differentiation in primary cultures with an IC50 of 3-10 x 10−11 M.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Abramovitz, M., Boie, Y., Nguyen, T., et al. Cloning and expression of a cDNA for the human prostanoid FP receptor. The Journal of Biological Chemisty 269(4), 2632-2636 (1994).

    2. Lake, S., Gullberg, H., Wahlqvist, J., et al. Cloning of the rat and human prostaglandin F2α receptors and the expression of the rat prostaglandin F2α receptor. FEBS Lett. 355(3), 317-325 (1994).

    3. Dukes, M., Russell, W., and Walpole, A.L. Potent luteolytic agents related to prostaglandin F2α. Nature 250(464), 330-331 (1974).

    4. Serrero, G., and Lepak, N.M. Prostaglandin F2α receptor (FP receptor) agonists are potent adipose differentiation inhibitors for primary culture of adipocyte precursors in defined medium. Biochem. Biophys. Res. Commun. 233(1), 200-202 (1997).

    Product Citations

    Ahmad, S.F., Akoum, A., and Horne, A.W. Selective modulation of the prostaglandin F2a pathway markedly impacts on endometriosis progression in a xenograft mouse model. Mol. Hum. Reprod. 21(12), 905-916 (2015).