CAS 209860-88-8|Tafluprost acid
| Common Name | Tafluprost acid | ||
|---|---|---|---|
| CAS Number | 209860-88-8 | Molecular Weight | 410.452 |
| Density | 1.3±0.1 g/cm3 | Boiling Point | 575.9±50.0 °C at 760 mmHg |
| Molecular Formula | C22H28F2O5 | Melting Point | / |
| MSDS | / | Flash Point | 302.1±30.1 °C |
Names
| Name | 7-[2-(3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl]hept-5-enoic acid |
|---|---|
| Synonym | More Synonyms |
Tafluprost acid BiologicalActivity
| Description | 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]. |
|---|---|
| Related Catalog | Research Areas >>Cardiovascular DiseaseResearch Areas >>EndocrinologySignaling Pathways >>GPCR/G Protein >>Prostaglandin ReceptorResearch Areas >>Neurological Disease |
| Target | Human FP Receptor:0.4 nM (Ki) Human FP Receptor:0.53 nM (EC50) EP3 Receptor:67 nM (IC50) |
| In Vitro | 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]. |
| References | [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. [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. [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. [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. |
Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
|---|---|
| Boiling Point | 575.9±50.0 °C at 760 mmHg |
| Molecular Formula | C22H28F2O5 |
| Molecular Weight | 410.452 |
| Flash Point | 302.1±30.1 °C |
| Exact Mass | 410.190491 |
| PSA | 86.99000 |
| LogP | 2.80 |
| Vapour Pressure | 0.0±1.7 mmHg at 25°C |
| Index of Refraction | 1.579 |
| InChIKey | KIQXRQVVYTYYAZ-VKVYFNERSA-N |
| SMILES | O=C(O)CCCC=CCC1C(O)CC(O)C1C=CC(F)(F)COc1ccccc1 |
Synonyms
| (5Z)-7-{(1R,2R,3R,5S)-2-[(1E)-3,3-Difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl}-5-heptenoic acid |
| 5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, (5Z)- |
| tafluprost acid |
