17-trifluoromethylphenyl trinor Prostaglandin F

Cayman Chemical Item Number 16890

17-trifluoromethylphenyl trinor PGF (CAS 221246-34-0)

17-trifluoromethylphenyl trinor Prostaglandin F2α (CAS 221246-34-0)

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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 unsubstituted or meta-substituted aromatic derivatives are the most potent FP receptor agonists.4 17-trifluoromethylphenyl 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 trinor PGF would act very much like the free acid of travoprost. 17-phenyl trinor PGF is a potent luteolytic and abortifacient, with a potency equal to or greater than fluprostenol and cloprostenol.4

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 deLong, M.A., Amburgey, J., Taylor, C., et al. Synthesis and in vitro evaluation of human FP-receptor selective prostaglandin analogues. Bioorg Med Chem Lett 10 1519-1522 (2000).

Synonyms
  • 17-trifluoromethylphenyl trinor PGF
Formal Name 9α,​11α,​15S-​trihydroxy-​17-​trifluoromethylphenyl-​18,​19,​20-​trinor-​prosta-​5Z,​13E-​dien-​1-​oic acid
CAS Number 221246-34-0
Molecular Formula C24H31O5F3
Formula Weight 456.5
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]​(/C=C/[C@@H]​(O)​CCC2=CC(C(F)​(F)​F)​=CC=C2)​[C@H]​(O)​C1
InCHI Code
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​1S/C24H31F3O5/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/h1,3,5-7,12-14,18-22,28-30H,2,4,8-11,15H2,(H,31,32)​/b3-1-,13-12+/t18-,19+,20+,21-,22+/m0/s1
InCHI Key
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CMLNDCUXASGBMQ-NQUQXYBYSA-N

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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 2014-04-24. Prices are subject to change without notice.

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