Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H26F3NO3.C6H14N4O2 |
Molecular Weight | 631.6857 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CCCNC(N)=N)C(O)=O.OC(=O)C[C@H]1CCC2=C1NC3=CC=C(OCC4=CC(=C(C=C4)C5CCCC5)C(F)(F)F)C=C23
InChI
InChIKey=GVPVVOSNDUAUKM-BPGOJFKZSA-N
InChI=1S/C26H26F3NO3.C6H14N4O2/c27-26(28,29)22-11-15(5-8-19(22)16-3-1-2-4-16)14-33-18-7-10-23-21(13-18)20-9-6-17(12-24(31)32)25(20)30-23;7-4(5(11)12)2-1-3-10-6(8)9/h5,7-8,10-11,13,16-17,30H,1-4,6,9,12,14H2,(H,31,32);4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t17-;4-/m10/s1
Molecular Formula | C6H14N4O2 |
Molecular Weight | 174.201 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | C26H26F3NO3 |
Molecular Weight | 457.4847 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
APD-334 (Etrasimod) was discovered as part of our internal effort to identify potent, centrally available, functional antagonists of the S1P1 receptor for use as next generation therapeutics for treating multiple sclerosis (MS) and other autoimmune diseases. APD334 is a potent functional antagonist of S1P1 and has a favorable PK/PD profile, producing robust lymphocyte lowering at relatively low plasma concentrations in several preclinical species. This new agent was efficacious in a mouse experimental autoimmune encephalomyelitis (EAE) model of MS and a rat collagen induced arthritis (CIA) model and was found to have appreciable central exposure. APD-334 has therapeutic potential in immune and inflammatory-mediated diseases such as ulcerative colitis, Crohn’s disease, and atopic dermatitis.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4333 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790 |
6.1 nM [EC50] | ||
Target ID: CHEMBL3230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790 |
147.0 nM [EC50] | ||
Target ID: CHEMBL2274 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790 |
24.4 nM [EC50] |
PubMed
Title | Date | PubMed |
---|---|---|
Discovery of APD334: Design of a Clinical Stage Functional Antagonist of the Sphingosine-1-phosphate-1 Receptor. | 2014 Dec 11 |
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Will novel oral formulations change the management of inflammatory bowel disease? | 2016 Jun |
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Modulation of sphingosine-1-phosphate in inflammatory bowel disease. | 2017 May |
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Interfering with leukocyte trafficking in Crohn's disease. | 2019 Feb-Apr |
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Cell Trafficking Interference in Inflammatory Bowel Disease: Therapeutic Interventions Based on Basic Pathogenesis Concepts. | 2019 Jan 10 |
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The Selective Sphingosine 1-Phosphate Receptor Modulator Etrasimod Regulates Lymphocyte Trafficking and Alleviates Experimental Colitis. | 2019 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT03950232
Ulcerative Colitis: APD-334 (Etrasimod) 2 mg tablet by mouth, once daily up to approximately 5 years
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790
Etrasimod (APD-334) 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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:14:26 GMT 2023
by
admin
on
Sat Dec 16 10:14:26 GMT 2023
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Record UNII |
MXE5EMA09L
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
723019
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admin on Sat Dec 16 10:14:26 GMT 2023 , Edited by admin on Sat Dec 16 10:14:26 GMT 2023
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C174726
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CD-138
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1206123-97-8
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MXE5EMA09L
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300000044580
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44624336
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MXE5EMA09L
Created by
admin on Sat Dec 16 10:14:26 GMT 2023 , Edited by admin on Sat Dec 16 10:14:26 GMT 2023
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