Etrasimod
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Grundinformationen
- CAS
1206123-37-6- Standard-SMILES
O=C(O)C[C@H]1CCc2c1[nH]c1ccc(OCc3ccc(C4CCCC4)c(C(F)(F)F)c3)cc21- InChIKey
MVGWUTBTXDYMND-QGZVFWFLSA-N- Summenformel
- C26H26F3NO3
- Durchschnittliche Molmasse
- 457,5 g/mol
- Monoisotopische Masse
- 457,18647835
Überblick
Etrasimod is an organic heterotricyclic compound that is 1,2,3,4-tetrahydrocyclopenta[b]indole substituted by carboxymethyl and [4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy groups at positions 3R and 7, respectively. It is a potent and functional antagonist of the sphingosine-1-phosphate-1 (S1P1) receptor (IC50 = 1.88 nM in CHO cells). It has a role as a sphingosine-1-phosphate receptor 1 antagonist, an antibacterial agent, an anti-inflammatory drug and an immunosuppressive agent. It is a member of cyclopentanes, a monocarboxylic acid, an organic heterotricyclic compound, an aromatic ether and a member of (trifluoromethyl)benzenes. It is a conjugate acid of an etrasimod(1-).
Namen und Bezeichner
- Bevorzugter Name
- Etrasimod
- IUPAC
- 2-[(3R)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid
- Englischer Name
- Etrasimod
- Summenformel
- C26H26F3NO3
- Molmasse
- 457.48
Namen und Synonyme
Etrasimod1206123-37-6APD334APD-334etrasimodum6WH8495MMHAPD-334(FREE ACID)2-[(3R)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid(R)-2-(7-(4-Cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl) acetic acid2-((3R)-7-((4-cyclopentyl-3-(trifluoromethyl)phenyl)methoxy)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl)acetic acidRefChem:1392962-((3R)-7-((4-cyclopentyl-3-(trifluoromethyl)phenyl)methoxy)-1H,2H,3H,4H-cyclopenta(b)indol-3-yl)acetic acid
Weitere Namen anzeigen
NeflamapimodKVX-745CS-2445APD 334Etrasimod, 10 mM in DMSOAPD 334Etrasimod,APD-334,LPL Receptor,Inhibitor,inhibit,APD 334,Lysophospholipid Receptor
(R)-2-(7-((4-cyclopentyl-3-(trifluoromethyl)benzyl)oxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acidEtrasimod [USAN]Etrasimod(APD334)CHEMBL3358920Etrasimod (USAN)[(3R)-7-{[4-Cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid(R)-2-[7-[[4-Cyclopentyl-3-(trifluoromethyl)benzyl]oxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic AcidMFCD28502134
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 6,4
- Polarare Oberfläche (TPSA)
- 62,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 6
- Schwere Atome
- 33
- Formalladung
- 0
- Komplexität
- 695
Experimentelle und physikochemische Eigenschaften
Human Drugs
Breast Feeding; Lactation; Milk, Human; Gastrointestinal Agents; Sphingosine 1 Phosphate Receptor Modulators
EMA approved medicines: Human medicine
Physikochemische Eigenschaften
- Siedepunkt
- 621.4 · 621.4±50.0 °C(Predicted)
- Dichte
- 1.326 · 1.326±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- 29 · 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)
- Aggregatzustand
- A crystalline solid
- pka
- 4.61 · 4.61±0.10(Predicted)
- Farbe
- 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
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
Protein BindingEtrasimod plasma protein binding is 97.9%.
Pharmacodynamics
Etrasimod causes a reduction in peripheral blood lymphocyte count. In UC-1 and UC-2, mean lymphocyte counts decreased to approximately 50% of baseline at 2 weeks (approximate mean blood lymphocyte counts 0.9 x 109/L) and the lower lymphocyte counts were maintained during treatment with etrasimod. Dose-response relationship analysis indicates there is a dose-dependent reduction in blood lymphocyte counts. After discontinuing etrasimod 2 mg once daily, the median time for peripheral blood lymphocytes to return to the normal range was 2.6 weeks, with approximately 90% of subjects in the normal range within 4.7 weeks. Etrasimod may result in a transient decrease in heart rate and AV conduction upon treatment initiation. In UC-1 and UC-2, the mean (SD) decrease in heart rate was 7.2 (8.98) bpm at 2 to 3 hours after the first dose of etrasimod on Day 1. At 2 times the maximum recommended dose, etrasimod does not cause clinically significant QTc interval prolongation. Reductions in absolute FEV1 were also observed in subjects treated with etrasimod.
Mechanism of Action
Etrasimod is a sphingosine 1-phosphate (S1P) receptor modulator that binds with high affinity to S1P receptors 1, 4, and 5 (S1P<sub>1,4,5</sub>). Etrasimod has minimal activity on S1P<sub>3</sub> (25-fold lower than C<sub>max</sub> at the recommended dose) and no activity on S1P<sub>2</sub>. Etrasimod partially and reversibly blocks the capacity of lymphocytes to egress from lymphoid organs, reducing the number of lymphocytes in peripheral blood. The mechanism by which etrasimod exerts therapeutic effects in UC is unknown but may involve the reduction of lymphocyte migration into the intestines.
Biological Half-LifeThe mean plasma elimination half-life (t<sub>1/2</sub>) of etrasimod is approximately 30 hours.
Metabolism/Metabolites
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