17-trifluoromethylphenyl-13,14-dihydro trinor Prostaglandin F

Cayman Chemical Item Number 16895

17-trifluoromethylphenyl-13,14-dihydro trinor PGF (CAS 294856-01-2)

17-trifluoromethylphenyl-13,14-dihydro trinor Prostaglandin F2α (CAS 294856-01-2)

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Description

A number of 17-phenyl trinor prostaglandin F (17-phenyl trinor PGF) derivatives have been approved for the treatment of glaucoma.1,2,3 Of these, the ones wherein the 13,14-double bond has been hydrogenated retain relatively good potency, but show a significantly reduced incidence of local irritant side effects.4 17-trifluoromethylphenyl-13,14-dihydro trinor PGF bears an aromatic ring which is reminiscent of the trifluoromethyl-phenoxy ring of travoprost ((+)-fluprostenol isopropyl ester). As an ocular hypotensive agent, it would be expected that 17-trifluoromethylphenyl-13,14-dihydro trinor PGF would act very much like the free acid of latanoprost.

1 Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of Bimatoprost (Lumigan™). Surv Ophthalmol 45 S337-S345 (2001).

2 Stjernschantz, J.W. From PGF-isopropyl ester to latanoprost: A review of the development of xalatan. The proper lecture. Invest Ophthamol Vis Sci 42(6) 1134-1145 (2001).

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

4 Resul, B., Stjernschantz, J., No, K., et al. Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agents. J Med Chem 36 243-248 (1993).

Synonyms
  • 17-trifluoromethylphenyl-13,14-dihydro trinor PGF
Formal Name 9α,​11α,​15R-​trihydroxy-​17-​(3-​(trifluoromethyl)phenyl)-​18,​19,​20-​trinor-​prosta-​5Z-​en-​1-​oic acid
CAS Number 294856-01-2
Molecular Formula C24H33O5F3
Formula Weight 458.5
Formulation A solution in methyl acetate
Purity ≥98%
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]​(CC[C@@H]​(O)​CCC2=CC(C(F)​(F)​F)​=CC=C2)​[C@H]​(O)​C1
InCHI Code
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​1S/C24H33F3O5/c25-24(26,27)​17-7-5-6-16(14-17)​10-11-18(28)​12-13-20-19(21(29)​15-22(20)​30)​8-3-1-2-4-9-23(31)​32/h1,3,5-7,14,18-22,28-30H,2,4,8-13,15H2,(H,31,32)​/b3-1-/t18-,19+,20+,21-,22+/m0/s1
InCHI Key
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GGAGMUSEFHEEBF-XPRPYWGDSA-N

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17-trifluoromethylphenyl-13,14-dihydro trinor Prostaglandin F2α is available in the following screening libraries:

Size Price Quantity Subtotal
1 mg $51.00 $0.00
5 mg $230.00 $0.00
10 mg $408.00 $0.00
100 mg $3,060.00 $0.00
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Cart Total $0.00

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Pricing updated 2014-04-16. Prices are subject to change without notice.

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