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15-keto Fluprostenol

Cayman Chemical Item Number 16785

15-keto Fluprostenol

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Description

Fluprostenol is an F-series prostaglandin analog which has been approved for many years as a luteolytic in veterinary animals.1 The isopropyl ester of fluprostenol (travoprost) was recently introduced as an ocular hypotensive drug.2 Oxidation of the C-15 hydroxyl group of fluprostenol produces 15-keto fluprostenol. 15-keto Fluprostenol is a potential metabolite of fluprostenol when administered to animals. 15-keto Fluprostenol is also one of the common minor impurities found in commercial preparations of the bulk drug compound. Products of β-oxidation account for most of the metabolites of fluprostenol recovered in plasma and urine. However, 15-keto fluprostenol is a minor metabolite, and one which could be enhanced in situations where β-oxidation is reduced.

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

2 Sorbera, L.A., and Castañer, J. Travoprost. Drugs Future 25 41-45 (2000).

Formal Name (±)15-​oxo-​9α,​11α-​dihydroxy-​16,​16-​(3-​(trifluoromethyl)phenoxy)-​17,​18,​19,​20-​tetranor-​prosta-​5Z,​13E-​dien-​1-​oic acid
Molecular Formula C23H27F3O6
Formula Weight 456.5
Formulation A solution in methyl acetate
Purity ≥98%
λmax 225 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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OC(=O)​CCC/C=C\CC1C(O)​CC(O)​[C@@H]​1\C=C\C(=O)​COc1cccc(c1)​C(F)​(F)​F

Background Reading

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

Sorbera, L.A., and Castañer, J. Travoprost. Drugs Future 25 41-45 (2000).

15-keto Fluprostenol is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $48.00 $0.00
5 mg $216.00 $0.00
10 mg $384.00 $0.00
50 mg $1,680.00 $0.00
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

11-keto Fluprostenol
15(S)-Fluprostenol
9-keto Fluprostenol
Fluprostenol isopropyl ester
Show all 4 Hide all but first 3

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