ETRASIMOD ARGININE

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 Search

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790 | https://www.arenapharm.com/pipeline/etrasimod/#

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	Potency
Sphingosine 1-phosphate receptor Edg-1 12 Target ID: CHEMBL4333 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790	Antagonist 2778	6.1 nM [EC50]
Sphingosine 1-phosphate receptor Edg-6 9 Target ID: CHEMBL3230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790	Antagonist 2778	147.0 nM [EC50]
Sphingosine 1-phosphate receptor Edg-8 9 Target ID: CHEMBL2274 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25516790	Antagonist 2778	24.4 nM [EC50]

PubMed

Title	Date	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 Created by `admin` on `Sat Dec 16 10:14:26 UTC 2023` Edited by `admin` on `Sat Dec 16 10:14:26 UTC 2023`
Record UNII	MXE5EMA09L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETRASIMOD ARGININE

Official Name

English

VELSIPITY

Brand Name

English

APD-334 L-ARGININE

Code

English

ETRASIMOD ARGININE [USAN]

Common Name

English

APD334 L-ARGININE

Code

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