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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
Structure of ETRASIMOD ARGININE

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

HIDE SMILES / InChI

Molecular Formula C6H14N4O2
Molecular Weight 174.201
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
6.1 nM [EC50]
147.0 nM [EC50]
24.4 nM [EC50]

PubMed

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
MXE5EMA09L
Record Status Validated (UNII)
Record Version