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Tafluprost (free acid)
Cayman Chemical Item Number 10005439
Description
A number of 17-phenyl trinor prostaglandin F2α (17-phenyl trinor PGF2α) derivatives have been approved for the treatment of glaucoma.1↗,2↗,3↗,4↗ 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.5↗ Alternatively, it was recently reported that analogs incorporating a 15-deoxy-15,15-difluoro modification also had a favorable ophthalmic activity profile.6↗ Tafluprost is a 2-series, 16-phenoxy analog of PGF2α with the 15,15-difluoro substitution. Tafluprost (free acid) is a very potent FP receptor agonist, with a Ki of 0.4 nM.6↗ The ester prodrug forms of tafluprost are also potent ocular hypotensives in monkeys.
Synonyms AFP-172
Formal Name 9α,11α-dihydroxy-15,15-difluoro-16-phenoxy-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-oic acid
CAS Number 209860-88-8
Molecular Formula C22H28F2O5
Formula Weight 410.5
Formulation A solution in methyl acetate
Purity >98%
λmax 269, 276 nm
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES O[C@@H](C[C@@H](O)[C@@H]1/C=C/C(F)(F)COC2=CC=CC=C2)[C@@H]1C/C=C\CCCC(O)=O
InCHI Code 1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+/t17-,18-,19+,20-/m1/s1
InCHI Key KIQXRQVVYTYYAZ-VKVYFNERSA-N |