9-keto Fluprostenol isopropyl ester

Cayman Chemical Item Number 16782

Fluprostenol Prostaglandin E2 (CAS 1219032-18-4)

9-keto Fluprostenol isopropyl ester (CAS 1219032-18-4)

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Description

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.

1 Dukes, M., Russell, W., and Walpole, A.L. Potent luteolytic agents related to prostaglandin F. 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).

Synonyms
  • Fluprostenol Prostaglandin E2
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
Molecular Formula C26H33F3O6
Formula Weight 498.5
Formulation A solution in ethanol
Purity ≥98%
λmax 222, 277 nm
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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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
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​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
InCHI Key
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OKXNVRDMSRTJEN-FFKVAXMCSA-N

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9-keto Fluprostenol isopropyl ester is available in the following screening library:

Size Price Quantity Subtotal
1 mg $71.00 $0.00
5 mg $320.00 $0.00
10 mg $568.00 $0.00
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Pricing updated 2014-04-23. Prices are subject to change without notice.

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