15(S)-Fluprostenol

Cayman Chemical Item Number 16787

(CAS 54276-24-3)

15(S)-Fluprostenol (CAS 54276-24-3)

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Description

(+)-15(R)-Fluprostenol isopropyl ester is a prodrug (Travoprost) which is converted by esterase enzymatic activity in the cornea to yield the corresponding free acid.1 The free acid, (+)-15(R)-fluprostenol, is a potent FP receptor agonist.2 The 15(R)-epimers of most prostaglandins are about 100 times less potent than the natural, 15(S)-isomers. However, the neighboring phenoxy group at C-16 reverses the absolute configuration at C-15 in the fluprostenol series; hence, 15(S)-fluprostenol is less active as an FP agonist than 15(R)-fluprostenol. The biology of 15(S)-fluprostenol has not been widely studied.

1 Stjernschantz, J., and Resul, B. Phenyl substituted prostaglandin analogs for glaucoma treatment. Drugs Future 17 691-704 (1992).

2 Abramovitz, M., Adam, M., Boie, Y., et al. The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs. Biochim Biophys Acta 1483 285-293 (2000).

Formal Name 9α,​11α,​15S-​trihydroxy-​16-​(3-​(trifluoromethyl)phenoxy)-​17,​18,​19,​20-​tetranor-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 54276-24-3
Molecular Formula C23H29F3O6
Formula Weight 458.5
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\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+/m0/s1
InCHI Key
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WWSWYXNVCBLWNZ-HBWANGNJSA-N

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15(S)-Fluprostenol is available in the following screening library:

Size Price Quantity Subtotal
1 mg $55.00 $0.00
5 mg $248.00 $0.00
10 mg $440.00 $0.00
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Pricing updated 2014-04-19. Prices are subject to change without notice.

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