| Identification | Back Directory | [Name]
Etrasimod | [CAS]
1206123-37-6 | [Synonyms]
APD334
CS-2445
Etrasimod
Neflamapimod
APD-334;APD 334
Etrasimod(APD334)
APD334; APD-334; APD 334; ETRASIMOD
(R)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
Cyclopent[b]indole-3-acetic acid, 7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydro-, (3R)- | [Molecular Formula]
C26H26F3NO3 | [MDL Number]
MFCD28502134 | [MOL File]
1206123-37-6.mol | [Molecular Weight]
457.48 |
| Chemical Properties | Back Directory | [Boiling point ]
621.4±50.0 °C(Predicted) | [density ]
1.326±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:29.0(Max Conc. mg/mL);63.39(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:1):0.5(Max Conc. mg/mL);1.09(Max Conc. mM)
DMF:30.0(Max Conc. mg/mL);65.57(Max Conc. mM)
Ethanol:12.5(Max Conc. mg/mL);27.32(Max Conc. mM) | [form ]
A crystalline solid | [pka]
4.61±0.10(Predicted) | [color ]
White to khaki | [InChIKey]
MVGWUTBTXDYMND-QGZVFWFLSA-N | [SMILES]
N1C2=C(C=C(OCC3=CC=C(C4CCCC4)C(C(F)(F)F)=C3)C=C2)C2CC[C@H](CC(O)=O)C1=2 |
| Hazard Information | Back Directory | [Uses]
Etrasimod (APD334) is a potent, selective and orally available antagonist of the sphingosine-1-phosphate-1 (S1P1) receptor with an IC50 value of 1.88 nM in CHO cells. | [in vivo]
APD334 has a relatively low systemic clearance (<4% of hepatic blood flow) and high Cmax across all species. In both dog and monkey a significant decrease in volume of distribution (Vss) is observed relative to rodent. Oral bioavailability is in the range of 40–100%, and the terminal phase half-life varied from 6 h in monkey, to as long as 29 h in dog. Rat and monkey t1/2 values for siponimod (another S1P1 modulator currently in human trials) have been disclosed and are 6 and 19 h, respectively[1]. | [References]
[1] Buzard DJ, et al. Discovery of APD334: Design of a Clinical Stage Functional Antagonist of the Sphingosine-1-phosphate-1 Receptor. ACS Med Chem Lett. 2014 Nov 4;5(12):1313-7. DOI:10.1021/ml500389m |
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