9-keto Fluprostenol isopropyl ester
Item № 16782
CAS № 1219032-18-4
Purity ≥98%
1 mg $71.00 $0.00
5 mg $320.00 $0.00
10 mg $568.00 $0.00

Pricing updated 2016-04-30. Prices are subject to change without notice.

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  • Fluprostenol Prostaglandin E2

Fluprostenol is a well-studied, potent analog of prostaglandin F (PGF) and acts primarily through the FP receptor.1 Oxidation at C-9 of fluprostenol yields 9-keto fluprostenol. Prostaglandin esters are known to be hydrolyzed in the eye to the corresponding free acids.2 However, the use of prostaglandin esters as prodrugs outside the eye is relatively unexplored. 9-keto Fluprostenol is an analog of PGE2 with structural modifications intended to give it a prolonged half-life and greater potency. 9-keto Fluprostenol isopropyl ester has the potential to act as an EP agonist in prodrug form. However, no studies on the pharmacology of this compound have been published to date. In addition 9-keto fluprostenol isopropyl ester is a potential metabolite of Travoprost, which is the Alcon trade name for fluprostenol isopropyl ester. In monkey cornea, this transformation was observed as a product of NADP+-dependent 15-hydroxyprostaglandin dehydrogenase when the closely related analog Latanoprost was used as a substrate.3 Certain F-series prostaglandins have been shown to be converted to the corresponding E-series compounds in rabbit liver4 and human platelet5 preparations.

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Technical Information
Formal Name (+)-9-oxo-11α,15R-dihydroxy-16-(3-(trifluoromethyl)phenoxy)-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-oic acid, isopropyl ester
CAS Number 1219032-18-4
  • Fluprostenol Prostaglandin E2
Molecular Formula C26H33F3O6
Formula Weight 498.5
Purity ≥98%
Formulation A solution in ethanol
λmax 222, 277 nm
SMILES O[C@H]1[C@H](/C=C/[C@@H](O)COC2=CC(C(F)(F)F)=CC=C2)[C@@H](C/C=C\CCCC(OC(C)C)=O)C(C1)=O
InChI Code 1S/C26H33F3O6/c1-17(2)35-25(33)11-6-4-3-5-10-21-22(24(32)15-23(21)31)13-12-19(30)16-34-20-9-7-8-18(14-20)26(27,28)29/h3,5,7-9,12-14,17,19,21-22,24,30,32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,24-/m1/s1

WARNING - This product is not for human or veterinary use.

Shipping & Storage
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
Stability As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
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References & Background Reading
Product Description References

1. Dukes, M., Russell, W., and Walpole, A.L. Potent luteolytic agents related to prostaglandin F2.alpha.. Nature 250 330-331 (1974).

2. Goh, Y., and Kishino, J. Pharmacological characterization of prostaglandin-related ocular hypotensive agents. Jpn J Ophthamol 38 236-245 (1994).

3. Fujimori, K., Okada, T., and Urade, Y. Expression of NADP+-dependent 15-hydroxyprostaglandin dehydrogenase mRNA in monkey ocular tissues and characterization of its recombinant enzyme. J Biochem 131 383-389 (2002).

4. Wong, P.Y., Malik, K.U., Desiderio, D.M., et al. Hepatic metabolism of prostacyclin (PGI2) in the rabbit: Formation of a potent novel inhibitor of platelet aggregation. Biochem Biophys Res Commun 93 486-494 (1980).

5. Wong, P.Y.K., Lee, W.H., Chao, P.H.W., et al. Metabolism of prostacyclin by 9-hydroxyprostaglandin dehydrogenase in human platelets. Formation of a potent inhibitor of platelet aggregation and enzyme purification. J Biol Chem 255(19) 9021-9024 (1980).

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