An ocular hypotensive agent
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17-trifluoromethylphenyl-13,14-dihydro trinor Prostaglandin F1α

Item No. 15895

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,11α,15S-trihydroxy-17-trifluoromethylphenyl-18,19,20-trinor-prostan-1-oic acid
CAS Number
1027401-98-4
Synonyms
  • 17-TFM-PGF1α
Molecular Formula
C24H35F3O5
Formula Weight
460.5
Purity
≥98%
Formulation (Request formulation change)
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
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
InChI=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
DSVAWVBHUBDAPY-AHJNKEMKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    A number of 17-aryl trinor and 16-aryloxy tetranor prostaglandin F2α 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 PGF1α (17-TFM-PGF1α) is a typical “ring” analog reminiscent of the trifluoromethyl-phenoxy ring of Travoprost. The a chain of 17-TFM-PGF1α 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-PGF1α would act very much like the free acid of latanoprost.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Woodward, D.F., Krauss, A.H., Chen, J., et al. The pharmacology of bimatoprost (Lumigan™). Surv. Ophthalmol. 45(Suppl. 4), S337-S345 (2001).

    2. Stjernschantz, J.W. From PGF2α-isopropyl ester to latanoprost: A review of the development of xalatan. The proper lecture. Invest. Ophthalmol. Vis. Sci. 42(6), 1134-1145 (2001).

    3. Sorbera, L.A., and Castañer, J. Travoprost. Drugs Future 25(1), 41-45 (2000).

    4. Resul, B., Stjernschantz, J., No, K., et al. Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agents. J. Med. Chem. 36(2), 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(14), 1519-1522 (2000).