15-keto Fluprostenol

Cayman Chemical Item Number 16785

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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 F. 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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O[C@@H]​1[C@H]​(C/C=C\CCCC(O)​=O)​[C@@H]​(/C=C/C(COC2=CC(C(F)​(F)​F)​=CC=C2)​=O)​[C@H]​(O)​C1
InCHI Code
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​1S/C23H27F3O6/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/h1,3,5-7,10-12,18-21,28-29H,2,4,8-9,13-14H2,(H,30,31)​/b3-1-,11-10+/t18-,19-,20+,21-/m1/s1
InCHI Key
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KWTWHYQJNRDZOJ-XXAASLTGSA-N

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

Size Price Quantity Subtotal
1 mg $49.00 $0.00
5 mg $221.00 $0.00
10 mg $392.00 $0.00
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Pricing updated 2015-04-18. Prices are subject to change without notice.

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Warning This product is not for human or veterinary use.

Related Products

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15(S)-Fluprostenol
9-keto Fluprostenol
Fluprostenol isopropyl ester
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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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Ann Arbor, Michigan 48108 USA

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