5-trans Fluprostenol

Cayman Chemical Item Number 16776

5,6-trans Fluprostenol (CAS 57968-83-9)

5-trans Fluprostenol (CAS 57968-83-9)

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Description

Travoprost is the Alcon trade name for fluprostenol isopropyl ester, an F-series prostaglandin analog which has been approved for use as an ocular hypotensive drug.1 Fluprostenol isopropyl ester is a prodrug which is converted by esterase enzymatic activity in the cornea to yield the corresponding free acid, fluprostenol.2 5-trans Fluprostenol is an impurity that is routinely found in bulk preparations of fluprostenol in amounts ranging from 1-3%. This impurity occurs in the finished prodrug Travoprost in similar amounts. The pharmacology of 5-trans fluprostenol has not been studied extensively to date.

1 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).

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

Synonyms
  • 5,6-trans Fluprostenol
Formal Name 9,​11,​15-​trihydroxy-​16-​(3-​(trifluoromethyl)phenoxy)-​17,​18,​19,​20-​tetranor-​prosta-​5E,​13E-​dien-​1-​oic acid
CAS Number 57968-83-9
Molecular Formula C23H29F3O6
Formula Weight 458.5
Formulation A solution in ethanol
Purity ≥95%
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/CCCC(O)​=O)​[C@@H]​(/C=C/[C@@H]​(O)​COC2=CC(C(F)​(F)​F)​=CC=C2)​[C@H]​(O)​C1
InCHI Code
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​1S/C23H29F3O6/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/h1,3,5-7,10-12,16,18-21,27-29H,2,4,8-9,13-14H2,(H,30,31)​/b3-1+,11-10+/t16-,18-,19-,20+,21-/m1/s1
InCHI Key
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WWSWYXNVCBLWNZ-BDFMIYKPSA-N

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Background Reading

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).

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

5-trans Fluprostenol is available in the following screening library:

Size Price Quantity Subtotal
1 mg $70.00 $0.00
5 mg $315.00 $0.00
10 mg $560.00 $0.00
Bulk Contact
Cart Total $0.00

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Pricing updated 2014-04-20. Prices are subject to change without notice.

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