An FP receptor agonist, a PGF2α derivative, and an active metabolite of tafluprost
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Labeled Version(s)
9002406Tafluprost (free acid)-d4
Pro-drug Form(s)
10005440Tafluprost
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Tafluprost (free acid)

Item No. 10005439

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid
CAS Number
209860-88-8
Synonyms
  • AFP-172
Molecular Formula
C22H28F2O5
Formula Weight
410.5
Purity
≥98%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDSMO: 30 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 3 mg/ml
λmax
269, 276 nm
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
InChI=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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $127

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    5 mg

    $560

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    10 mg

    $995

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    25 mg

    $2,172

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    Product Description

    Tafluprost (free acid) is an FP receptor agonist (Ki = 4 nM for the human receptor), a derivative of prostaglandin F2α (PGF2α; Item Nos. 16010 | 16020), and an active metabolite of the prodrug tafluprost (Item No. 10005440).1 It is formed from tafluprost by hydrolysis and is selective for the FP receptor over the dopamine receptor and PGE2 receptor subtypes EP1 and EP2, as well as a panel of 32 neurological receptors and transporters, at 1 µM. Tafluprost (free acid) induces constriction in isolated cat iris sphincters (EC50 = 0.6 nM).2 It also increases the proliferation and migration of, capillary formation by, and COX-2 levels in, human umbilical vein endothelial cells (HUVECs) when used at a concentration of 100 µM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Takagi, Y., Nakajima, T., Shimazaki, A., et al. Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp. Eye Res. 78(4), 767-776 (2004).

    2. Nakajima, T., Matsugi, T., Goto, W., et al. New fluoroprostaglandin F2α derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol. Pharm. Bull. 26(12), 1691-1695 (2003).

    3. Roh, Y.J., Park, Y.G., Kang, S., et al. Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch. Clin. Exp. Ophthalmol. 250(12), 1765-1775 (2012).

    Product Citations

    Roh, Y.J., Park, Y.G., Kang, S., et al. Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch. Clin. Exp. Ophthalmol. 250(12), 1765-1775 (2012).