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

Cayman Chemical Item Number 15895

17-TFM-PGF (CAS 1027401-98-4)

17-trifluoromethylphenyl-13,14-dihydro trinor Prostaglandin F1α (CAS 1027401-98-4)

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Description

A number of 17-aryl trinor and 16-aryloxy tetranor prostaglandin F derivatives have been approved for the treatment of glaucoma.1,2,3 These “ring” prostaglandin (PG) analogs have improved efficacy over the PGs with an n-alkyl lower side chain. 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 (17-TFM-PGF) is a typical “ring” analog reminiscent of the trifluoromethyl-phenoxy ring of Travoprost. The a chain of 17-TFM-PGF is saturated, making this compound a formal member of the one-series PGs. Recent work has shown that in the “ring” series of analogs, this modification has little impact on FP receptor binding.5 As an ocular hypotensive agent, it is expected that 17-TFM-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).

5 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-TFM-PGF
Formal Name 9α,​11α,​15S-​trihydroxy-​17-​trifluoromethylphenyl-​18,​19,​20-​trinor-​prostan-​1-​oic acid
CAS Number 1027401-98-4
Molecular Formula C24H35F3O5
Formula Weight 460.5
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]​(CCCCCCC(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/C24H35F3O5/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/h5-7,14,18-22,28-30H,1-4,8-13,15H2,(H,31,32)​/t18-,19+,20+,21-,22+/m0/s1
InCHI Key
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DSVAWVBHUBDAPY-AHJNKEMKSA-N

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17-trifluoromethylphenyl-13,14-dihydro trinor Prostaglandin F1α 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
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Pricing updated 2014-04-17. Prices are subject to change without notice.

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