OZANIMOD

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H24N4O3
Molecular Weight	404.4617
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC1=CC=C(C=C1C#N)C2=NC(=NO2)C3=C4CC[C@H](NCCO)C4=CC=C3

InChI

InChIKey=XRVDGNKRPOAQTN-FQEVSTJZSA-N

InChI=1S/C23H24N4O3/c1-14(2)29-21-9-6-15(12-16(21)13-24)23-26-22(27-30-23)19-5-3-4-18-17(19)7-8-20(18)25-10-11-28/h3-6,9,12,14,20,25,28H,7-8,10-11H2,1-2H3/t20-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H24N4O3
Molecular Weight	404.4617
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Ozanimod (previously known as RPC-1063) is a selective immune-inflammatory modulator of the G protein-coupled receptors sphingosine 1-phosphate 1 and 5, which are part of the sphingosine 1-phosphate (S1P) receptor family. Treatment with S1P receptor modulators interferes with S1P signaling and blocks the response of lymphocytes (a type of white blood cell) to exit signals from the lymph nodes, sequestering them within the nodes. The result is a downward modulation of circulating lymphocytes and anti-inflammatory activity by inhibiting cell migration to sites of inflammation. Ozanimod is currently in phase III clinical trials for the treatment of relapsing multiple sclerosis (RMS) and ulcerative colitis, and also in phase II clinical trials to determine whether it is effective in the treatment of Crohn's disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sphingosine 1-phosphate receptor 5 4	Agonist 2361	Ulcerative Colitis	11.0 nM [EC50]
Sphingosine 1-phosphate receptor 1 7	Agonist 2361	Ulcerative Colitis	0.41 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase
Ulcerative Colitis 85	Primary	Sphingosine 1-phosphate receptor 5 Sphingosine 1-phosphate receptor 1	Phase III 636
Crohn's Disease 17	Primary	Sphingosine 1-phosphate receptor 5 Sphingosine 1-phosphate receptor 1	Phase II 1079
Multiple Sclerosis 98	Primary	Sphingosine 1-phosphate receptor 5 Sphingosine 1-phosphate receptor 1	Phase III 636

PubMed

Title	Date	PubMed
Ozanimod (RPC1063) is a potent sphingosine-1-phosphate receptor-1 (S1P1 ) and receptor-5 (S1P5 ) agonist with autoimmune disease-modifying activity.	2016 Jun	26990079
Ozanimod Induction and Maintenance Treatment for Ulcerative Colitis.	2016 May 5	27144850

Patents

Sample Use Guides

In Vivo Use Guide

Multiple Sclerosis: 1 mg RPC1063 (Ozanimod) oral capsule daily

Route of Administration: Oral

In Vitro Use Guide

Ozanimod (RPC1063) is a specific agonist for sphingosine-1-phosphate receptor subtypes 1 (S1P1) and S1P5 receptors. The EC50 values were 0.16 nM and 0.41 nM for S1P1 receptors in the inhibition of cAMP generation and [35S]-GTPγS binding. The 83% Emax value of ozanimod against S1P5 receptor was 11 nM. RPC1063 demonstrated a dose‐dependent effect on S1P1 receptor re‐expression on the cell surface, with near complete and sustained loss of cell surface receptor expression at concentrations above 10 nM in S1P1 receptor-HEK293T cells after 1 h incubation.

Substance Class	Chemical Created by `admin` on `Mon Oct 21 22:49:10 UTC 2019` Edited by `admin` on `Mon Oct 21 22:49:10 UTC 2019`
Record UNII	Z80293URPV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OZANIMOD

Official Name

English

OZANIMOD [WHO-DD]

Common Name

English

RPC-1063

Code

English

BENZONITRILE, 5-(3-((1S)-2,3-DIHYDRO-1-((2-HYDROXYETHYL)AMINO)-1H-INDEN-4-YL)-1,2,4-OXADIAZOL-5-YL)-2-(1-METHYLETHOXY)-

Systematic Name

English

OZANIMOD [USAN]

Common Name

English

OZANIMOD [INN]

Common Name

English

RPC1063

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

499515