ETRASIMOD

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H26F3NO3
Molecular Weight	457.4847
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C[C@H]1CCC2=C1NC3=CC=C(OCC4=CC(=C(C=C4)C5CCCC5)C(F)(F)F)C=C23

InChI

InChIKey=MVGWUTBTXDYMND-QGZVFWFLSA-N

InChI=1S/C26H26F3NO3/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/h5,7-8,10-11,13,16-17,30H,1-4,6,9,12,14H2,(H,31,32)/t17-/m1/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

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
Discovery of APD334: Design of a Clinical Stage Functional Antagonist of the Sphingosine-1-phosphate-1 Receptor.	2014 Dec 11	25516790
Will novel oral formulations change the management of inflammatory bowel disease?	2016 Jun	26967267
Modulation of sphingosine-1-phosphate in inflammatory bowel disease.	2017 May	28279838
Targeting Cytokine Signaling and Lymphocyte Traffic via Small Molecules in Inflammatory Bowel Disease: JAK Inhibitors and S1PR Agonists.	2019	30930775
Interfering with leukocyte trafficking in Crohn's disease.	2019 Feb-Apr	31327399
Cell Trafficking Interference in Inflammatory Bowel Disease: Therapeutic Interventions Based on Basic Pathogenesis Concepts.	2019 Jan 10	30165490
The Selective Sphingosine 1-Phosphate Receptor Modulator Etrasimod Regulates Lymphocyte Trafficking and Alleviates Experimental Colitis.	2019 Jun	30872391

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 10:14:25 UTC 2023` Edited by `admin` on `Sat Dec 16 10:14:25 UTC 2023`
Record UNII	6WH8495MMH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETRASIMOD

Official Name

English

(R)-2-(7-(4-CYCLOPENTYL-3-(TRIFLUOROMETHYL)BENZYLOXY)-1,2,3,4-TETRAHYDROCYCLOPENTA(B)INDOL-3-YL) ACETIC ACID

Systematic Name

English

APD334

Code

English

ETRASIMOD [USAN]

Common Name

English

APD-334(FREE ACID)

Code

English

Etrasimod [WHO-DD]

Common Name

English

CYCLOPENT(B)INDOLE-3-ACETIC ACID, 7-((4-CYCLOPENTYL-3-(TRIFLUOROMETHYL)PHENYL)METHOXY)-1,2,3,4-TETRAHYDRO-, (3R)-

Systematic Name

English

APD-334

Code

English

[(3R)-7-{[4-Cyclopentyl-3-(trifluoromethyl)phenyl]methoxy}-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid

Systematic Name

English

etrasimod [INN]

Common Name

English

Code System Code Type Description

DRUG BANK

DB14766