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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=C2C=C(OCC4=CC(=C(C=C4)C5CCCC5)C(F)(F)F)C=C3

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 C26H26F3NO3
Molecular Weight 457.4847
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
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

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

2023
446
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 6.1 nM [EC50]
Antagonist
2849
 147.0 nM [EC50]
Antagonist
2849
 24.4 nM [EC50]
PubMed

PubMed

TitleDatePubMed
Discovery of APD334: Design of a Clinical Stage Functional Antagonist of the Sphingosine-1-phosphate-1 Receptor.
2014 Dec 11
Will novel oral formulations change the management of inflammatory bowel disease?
2016 Jun
Modulation of sphingosine-1-phosphate in inflammatory bowel disease.
2017 May
Targeting Cytokine Signaling and Lymphocyte Traffic via Small Molecules in Inflammatory Bowel Disease: JAK Inhibitors and S1PR Agonists.
2019

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
Created
by admin
on Mon Mar 31 23:07:48 GMT 2025
Edited
by admin
on Mon Mar 31 23:07:48 GMT 2025
Record UNII
MXE5EMA09L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APD334 L-ARGININE
Preferred Name English
ETRASIMOD ARGININE
USAN  
USAN  
Official Name English
VELSIPITY
Brand Name English
APD-334 L-ARGININE
Code English
ETRASIMOD ARGININE [USAN]
Common Name English
Etrasimod arginine [WHO-DD]
Common Name English
L-ARGININE, (3R)-7-((4-CYCLOPENTYL-3-(TRIFLUOROMETHYL)PHENYL)METHOXY)-1,2,3,4-TETRAHYDROCYCLOPENT(B)INDOLE-3-ACETATE (1:1)
Systematic Name English
L-ARGININE MONO((3R)-7-((4-CYCLOPENTYL-3-(TRIFLUOROMETHYL)PHENYL)METHOXY)-1,2,3,4-TETRAHYDROCYCLOPENTA(B)INDOL-3-YL)ACETATE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 723019
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C174726
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
PRIMARY
USAN
CD-138
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
PRIMARY
CAS
1206123-97-8
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
PRIMARY
DAILYMED
MXE5EMA09L
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
PRIMARY
SMS_ID
300000044580
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
PRIMARY
PUBCHEM
44624336
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
PRIMARY
FDA UNII
MXE5EMA09L
Created by admin on Mon Mar 31 23:07:48 GMT 2025 , Edited by admin on Mon Mar 31 23:07:48 GMT 2025
PRIMARY
Related Record Type Details
Structure of ETRASIMOD
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ETRASIMOD
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
COLOR PHYSICAL
SOLUBILITY CHEMICAL pH
CHEMICAL
MELTING POINT PHYSICAL
NIH
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