에트라시모드
Etrasimod
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기본 정보
- CAS
1206123-37-6- 표준 SMILES
O=C(O)C[C@H]1CCc2c1[nH]c1ccc(OCc3ccc(C4CCCC4)c(C(F)(F)F)c3)cc21- InChIKey
MVGWUTBTXDYMND-QGZVFWFLSA-N- 분자식
- C26H26F3NO3
- 평균 분자량
- 457.5 g/mol
- 단동위원소 질량
- 457.18647835
개요
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-).
이름 및 식별자
- 우선 이름
- Etrasimod
- IUPAC
- 2-[(3R)-7-[[4-cyclopentyl-3-(trifluoromethyl)phenyl]methoxy]-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid
- 현지명
- 에트라시모드
- 영어명
- Etrasimod
- 분자식
- C26H26F3NO3
- 분자량
- 457.48
이름 및 동의어
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
이름 더 보기
에트라시모드NeflamapimodKVX-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
물성
구조 계산 물성보충 중
- XLogP
- 6.4
- 극성 표면적
- 62.3 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 6
- 회전 가능 결합 수
- 6
- 무거운 원자 수
- 33
- 형식 전하
- 0
- 복잡도
- 695
실험 및 물리화학적 성질
Human Drugs
Breast Feeding; Lactation; Milk, Human; Gastrointestinal Agents; Sphingosine 1 Phosphate Receptor Modulators
EMA approved medicines: Human medicine
물리화학적 성질
- 끓는 점
- 621.4 · 621.4±50.0 °C(Predicted)
- 밀도
- 1.326 · 1.326±0.06 g/cm3(Predicted)
- 저장 조건
- -20 °C · Store at -20°C
- 용해도
- 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)
- 물리적 상태
- 결정성 고체
- 산도 계수 (pKa)
- 4.61 · 4.61±0.10(Predicted)
- 색상
- 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
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
독성 정보
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
안전 데이터
- 신호 어
- Warning
- 유해·위험 문구
- 암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302
화학 및 산업
약리 정보
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
Etrasimod is metabolized by oxidation and dehydrogenation mediated primarily by CYP2C8, CYP2C9, and CYP3A4, with a minor contribution by CYP2C19 and CYP2J2. Etrasimod also undergoes conjugation primarily mediated by UGTs, with a minor contribution by sulfotransferases. Unchanged etrasimod is the main circulating component in plasma.
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