Tafluprost acid

• CAT Number: R031916
• CAS Number: 209860-88-8
• Molecular Formula: C22H28F2O5
• Molecular Weight: 410.45
• Purity: ≥95%
• Synonyms: (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid
• InChI: 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
• InChIKey: KIQXRQVVYTYYAZ-VKVYFNERSA-N
• SMILES: C1C(C(C(C1O)C=CC(COC2=CC=CC=C2)(F)F)CC=CCCCC(=O)O)O

Tafluprost acid (AFP-172), an active metabolic form of Tafluprost, is a selective prostanoid FP receptor agonist. Tafluprost acid shows a high affinity for human prostanoid FP receptor with Ki and EC50 values of 0.4 nM and 0.53 nM, respectively. Tafluprost acid has 126 times weaker binding affinity for prostanoid EP3 receptor (IC50=67 nM) than for the prostanoid FP receptor. Tafluprost acid can be used in the research of glaucoma[1][2][3].
Tafluprost acid (10, 100 nM, added on days 0 and 2) significantly inhibits adipogenesis in the early and late stages of differentiation of 3T3-L1 preadipocytes[2].
Tafluprost acid (100 nM, added on day 2 after initiating differentiation) suppresses adipogenesis in wild-type but not in FP knockout mouse primary adipocytes[2].
Tafluprost acid (10-4 M, 6 hours) stimulates the proliferation, migration of human umbilical vascular endothelial cells (HUVECs)[4].
Tafluprost acid (10-4 M, 4-18 hours) stimulates the tube formation of HUVECs[4].

Reference

[1]. Takagi Y, et al. Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76.
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[2]. Taketani Y, et al. Activation of the prostanoid FP receptor inhibits adipogenesis leading to deepening of the upper eyelid sulcus in prostaglandin-associated periorbitopathy. Invest Ophthalmol Vis Sci. 2014 Mar 4;55(3):1269-76.
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[3]. Fuwa M, et al. Advantages of Efficacy and Safety of Fixed-Dose Tafluprost/Timolol Combination Over Fixed-Dose Latanoprost/Timolol Combination. PLoS One. 2016 Jul 6;11(7):e0158797.
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[4]. Roh YJ, et al. Effects of AFP-172 on COX-2-induced angiogenic activities on human umbilical vein endothelial cells. Graefes Arch Clin Exp Ophthalmol. 2012 Dec;250(12):1765-75.
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