PONESIMOD

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H25ClN2O4S
Molecular Weight	460.9755
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC/N=C\1/N(c2ccccc2C)C(=O)/C(=C(\[H])/c3ccc(c(c3)Cl)OC[C@@]([H])(CO)O)/S1

InChI

InChIKey=LPAUOXUZGSBGDU-STDDISTJSA-N

InChI=1S/C23H25ClN2O4S/c1-3-10-25-23-26(19-7-5-4-6-15(19)2)22(29)21(31-23)12-16-8-9-20(18(24)11-16)30-14-17(28)13-27/h4-9,11-12,17,27-28H,3,10,13-14H2,1-2H3/b21-12-,25-23-/t17-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H25ClN2O4S
Molecular Weight	460.9755
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27108115 | https://www.mstrust.org.uk/a-z/ponesimod | https://adisinsight.springer.com/drugs/800024855

Ponesimod is an experimental drug for the treatment of multiple sclerosis (MS) graft-versus-host disease and psoriasis. It acts on certain types of white blood cells (lymphocytes) which are involved in the autoimmune attack on myelin seen in multiple sclerosis (MS). Ponesimod is an orally active, reversible, and selective sphingosine-1-phosphate receptor (S1PR1) modulator. The drug is in phase II clinical trial for the treatment of graft-versus-host disease. In addition, the phase III clinical trial comparing ponesimod to teriflunomide in relapsing-remitting MS is ongoing.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sphingosine 1-phosphate receptor Edg-1 9 Target ID: CHEMBL4333 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28489480 \| https://www.ncbi.nlm.nih.gov/pubmed/28812220	Modulator 780		5.0 nM [EC50]

PubMed

Title	Date	PubMed
Clinical pharmacology, efficacy, and safety aspects of sphingosine-1-phosphate receptor modulators.	2016 Aug	27249325
Modeling clinical efficacy of the S1P receptor modulator ponesimod in psoriasis.	2018 Feb	29174115
Modeling Tolerance Development for the Effect on Heart Rate of the Selective S1P₁ Receptor Modulator Ponesimod.	2018 Jun	28913826
Oral Therapies for Multiple Sclerosis.	2019 Jan 2	29500302
Discovery of Soft-Drug Topical Tool Modulators of Sphingosine-1-phosphate Receptor 1 (S1PR1).	2019 Mar 14	30891137

Substance Class	Chemical Created by `admin` on `Fri Jun 25 22:17:43 UTC 2021` Edited by `admin` on `Fri Jun 25 22:17:43 UTC 2021`
Record UNII	5G7AKV2MKP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PONESIMOD

Official Name

English

5-(3-CHLORO-4-(((2R)-2,3-DIHYDROXYPROPYL)OXY)BENZ-(Z)-YLIDENE)-2-((Z)-PROPYLIMINO)-3-(O-TOLYL)THIAZOLIDIN-4-ONE

Common Name

English

(2Z,5Z)-5-(3-CHLORO-4-((2R)-2,3-DIHYDROXYPROPOXY)BENZYLIDENE)-3-(2-METHYLPHENYL)-2-(PROPYLIMINO)-1,3-THIAZOLIDIN-4-ONE

Systematic Name

English

ACT-128800

Code

English

PONESIMOD [USAN]

Common Name

English

(2Z,5Z)-5-(3-CHLORO-4-((2R)-2,3-DIHYDROXYPROPOXY)PHENYLMETHYLIDENE)-3-(2-METHYLPHENYL)-2-(PROPYLIMINO)-1,3-THIAZOLIDIN-4-ONE

Systematic Name

English

PONESIMOD [INN]

Common Name

English

4-THIAZOLIDINONE, 5-((3-CHLORO-4-((2R)-2,3-DIHYDROXYPROPOXY)PHENYL)METHYLENE)-3-(2-METHYLPHENYL)-2-(PROPYLIMINO)-, (2Z,5Z)-

Systematic Name

English

PONVORY

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308