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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H25ClN2O4S
Molecular Weight 460.974
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of PONESIMOD

SMILES

CCC\N=C1/S\C(=C/C2=CC=C(OC[C@H](O)CO)C(Cl)=C2)C(=O)N1C3=CC=CC=C3C

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 460.974
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 2
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

PubMed

PubMed

TitleDatePubMed
Clinical pharmacology, efficacy, and safety aspects of sphingosine-1-phosphate receptor modulators.
2016 Aug
Sphingosine 1-Phosphate Receptor Modulators for the Treatment of Multiple Sclerosis.
2017 Oct
S1P(1) Modulator-Induced G (α)(i) Signaling and β-Arrestin Recruitment Are Both Necessary to Induce Rapid and Efficient Reduction of Blood Lymphocyte Count In Vivo.
2018 Feb
Modeling clinical efficacy of the S1P receptor modulator ponesimod in psoriasis.
2018 Feb
Ponesimod, a selective sphingosine 1-phosphate (S1P(1)) receptor modulator for autoimmune diseases: review of clinical pharmacokinetics and drug disposition.
2018 May
Discovery of super soft-drug modulators of sphingosine-1-phosphate receptor 1.
2018 Oct 15
Oral small molecules for psoriasis.
2018 Sep
Oral Therapies for Multiple Sclerosis.
2019 Jan 2
Cardiodynamic Interactions between Two S1P(1) Receptor Modulators in an Experimental Clinical Setting: Different Pharmacokinetic Properties as an Opportunity to Mitigate First-Dose Heart Rate Effects.
2019 Jul 1
Therapeutic Potential of Ponesimod Alone and in Combination with Dimethyl Fumarate in Experimental Models of Multiple Sclerosis.
2019 Mar 1
Discovery of Soft-Drug Topical Tool Modulators of Sphingosine-1-phosphate Receptor 1 (S1PR1).
2019 Mar 14
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:58:24 UTC 2023
Edited
by admin
on Sat Dec 16 17:58:24 UTC 2023
Record UNII
5G7AKV2MKP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PONESIMOD
INN   USAN  
INN   USAN  
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
PONESIMOD [ORANGE BOOK]
Common 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
Ponesimod [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C308
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1096146
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
DRUG BANK
DB12016
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
EPA CompTox
DTXSID50234631
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
WIKIPEDIA
Ponesimod
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
NCI_THESAURUS
C96534
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
EVMPD
SUB182605
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
RXCUI
2532300
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
ChEMBL
CHEMBL2108311
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
SMS_ID
100000169012
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
FDA UNII
5G7AKV2MKP
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
USAN
CD-143
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
INN
9150
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
CAS
854107-55-4
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
DAILYMED
5G7AKV2MKP
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
MESH
C550169
Created by admin on Sat Dec 16 17:58:25 UTC 2023 , Edited by admin on Sat Dec 16 17:58:25 UTC 2023
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
mainly binding to albumin and alpha-1-acid glycoprotein
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
single oral administration
FECAL
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TARGET -> AGONIST
EC50
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
ORAL BIOAVAILABILITY PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC