15-keto Fluprostenol isopropyl ester Exclusive

Cayman Chemical Item Number 16786

15-keto Travoprost (CAS 404830-45-1)

15-keto Fluprostenol isopropyl ester (CAS 404830-45-1)

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Description

Travoprost is an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug.1,2 Oxidation of the C-15 hydroxyl group without isopropyl ester hydrolysis produces 15-keto fluprostenol isopropyl ester (15-keto travoprost). 15-keto Travoprost is a potential metabolite of travoprost when administered to intact animals. 15-keto Travoprost is also one of the common minor impurities found in commercial preparations of the bulk drug compound. In general, F-series prostaglandin analogs with a 15-keto functional group lose a great deal of their FP receptor binding affinity, but retain enough to show a continued weak IOP hypotensive response.3 The efficacy of 15-keto travoprost as an ocular hypotensive has not been established.

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

2 Hellberg, M.R., Sallee, V.L., Mclaughlin, M.A., et al. Preclinical efficacy of travoprost, a potent and selective FP prostaglandin receptor agonist. J Ocul Pharmacol Ther 17(5) 421-432 (2001).

3 Taniguchi, T., Haque, M.S.R., Sugiyama, K., et al. Ocular hypotensive mechanism of topical isopropyl unoprostone, a novel prostaglandin metabolite-related drug, in rabbits. J Ocul Pharmacol 12 489-498 (1996).

Synonyms
  • 15-keto Travoprost
Formal Name (±)-​15-​oxo-​9α,​11α-​dihydroxy-​16-​(3-​(trifluoromethyl)phenoxy)-​17,​18,​19,​20-​tetranor-​prosta-​5Z,​13E-​dien-​1-​oic acid,​ isopropyl ester
CAS Number 404830-45-1
Molecular Formula C26H33F3O6
Formula Weight 498.5
Formulation A solution in methyl acetate
Purity ≥98%
λmax 224 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\CCCC(OC(C)​C)​=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/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/h3,5,7-9,12-14,17,21-24,31-32H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t21-,22-,23+,24-/m1/s1
InCHI Key
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KSDDYCRRTVADFZ-OHDKTVHDSA-N

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

Size Price Quantity Subtotal
1 mg $71.00 $0.00
5 mg $320.00 $0.00
10 mg $568.00 $0.00
25 mg $1,243.00 $0.00
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Pricing updated 2014-04-25. Prices are subject to change without notice.

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