Tafluprost acid

Modify Date: 2024-01-03 06:16:40

Tafluprost acid Structure
Tafluprost acid structure
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 N/A
MSDS N/A Flash Point 302.1±30.1 °C

 Use of Tafluprost acid


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].

 Names

Name 7-[2-(3,3-difluoro-4-phenoxybut-1-enyl)-3,5-dihydroxycyclopentyl]hept-5-enoic acid
Synonym More Synonyms

 Tafluprost acid Biological Activity

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
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

 Synthetic Route

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Tafluprost acid Structure

Tafluprost acid

CAS#:209860-88-8

Literature: DR.REDDYS LABORATORIES LIMITED; JACKSON, Mark P Patent: WO2013/118058 A1, 2013 ; Location in patent: Page/Page column 10-11 ;

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Tafluprost acid Structure

Tafluprost acid

CAS#:209860-88-8

Literature: DR.REDDYS LABORATORIES LIMITED; JACKSON, Mark P Patent: WO2013/118058 A1, 2013 ;

~%

Tafluprost acid Structure

Tafluprost acid

CAS#:209860-88-8

Literature: DR.REDDYS LABORATORIES LIMITED; JACKSON, Mark P Patent: WO2013/118058 A1, 2013 ;

~%

Tafluprost acid Structure

Tafluprost acid

CAS#:209860-88-8

Literature: EVERLIGHT USA, INC.; TSAI, Chia-Chung; CHEN, Chien-Yuh; LIANG, Sen-Bau; LO, Yu-Chi; YAO, Chi-Hsiang Patent: US2014/51882 A1, 2014 ;

~%

Tafluprost acid Structure

Tafluprost acid

CAS#:209860-88-8

Literature: EVERLIGHT USA, INC.; TSAI, Chia-Chung; CHEN, Chien-Yuh; LIANG, Sen-Bau; LO, Yu-Chi; YAO, Chi-Hsiang Patent: US2014/51882 A1, 2014 ;

~%

Tafluprost acid Structure

Tafluprost acid

CAS#:209860-88-8

Literature: EVERLIGHT USA, INC.; TSAI, Chia-Chung; CHEN, Chien-Yuh; LIANG, Sen-Bau; LO, Yu-Chi; YAO, Chi-Hsiang Patent: US2014/51882 A1, 2014 ;

 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