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Details

Stereochemistry ACHIRAL
Molecular Formula C29H35F3N2O3
Molecular Weight 516.595
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of Siponimod

SMILES

CCC1=CC(=CC=C1CN2CC(C2)C(O)=O)C(\C)=N\OCC3=CC=C(C4CCCCC4)C(=C3)C(F)(F)F

InChI

InChIKey=KIHYPELVXPAIDH-HNSNBQBZSA-N
InChI=1S/C29H35F3N2O3/c1-3-21-14-23(10-11-24(21)15-34-16-25(17-34)28(35)36)19(2)33-37-18-20-9-12-26(22-7-5-4-6-8-22)27(13-20)29(30,31)32/h9-14,22,25H,3-8,15-18H2,1-2H3,(H,35,36)/b33-19+

HIDE SMILES / InChI
Molecular Formula C29H35F3N2O3
Molecular Weight 516.595
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:15 UTC 2023
Edited
by admin
on Sat Dec 16 01:37:15 UTC 2023
Record UNII
RR6P8L282I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Siponimod
INN   WHO-DD  
USAN   INN  
Official Name English
1-[[4-[(1E)-1-[[[4-Cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino]ethyl]-2-ethylphenyl]methyl]-3-azetidinecarboxylic acid
Systematic Name English
3-Azetidinecarboxylic acid, 1-[[4-[(1E)-1-[[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino]ethyl]-2-ethylphenyl]methyl]-
Systematic Name English
siponimod [INN]
Common Name English
NVP-BAF312-NX
Code English
Siponimod [WHO-DD]
Common Name English
BAF312
Code English
BAF-312
Code English
SIPONIMOD [USAN]
Common Name English
SIPONIMOD [MI]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 437614
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
FDA ORPHAN DRUG 413413
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
NCI_THESAURUS C308
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
EU-Orphan Drug EU/3/14/1370
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
Code System Code Type Description
DAILYMED
RR6P8L282I
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
LACTMED
Siponimod
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
INN
9491
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
RXCUI
2121085
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
USAN
FG-55
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
WIKIPEDIA
Siponimod
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
CAS
1230487-00-9
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
SMS_ID
100000163287
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
MERCK INDEX
m12146
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
PUBCHEM
44599207
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID40153847
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
EVMPD
SUB177510
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
DRUG CENTRAL
5326
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
DRUG BANK
DB12371
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
NCI_THESAURUS
C152368
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
ChEMBL
CHEMBL2336071
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
FDA UNII
RR6P8L282I
Created by admin on Sat Dec 16 01:37:15 UTC 2023 , Edited by admin on Sat Dec 16 01:37:15 UTC 2023
PRIMARY
Related Record Type Details
SPHINGOSINE 1-PHOSPHATE RECEPTOR 5
TARGET -> AGONIST
Blocks the capacity of lymphocytes to egress from lymph nodes, reducing the number of lymphocytes in peripheral blood. Initial receptor activation is paradoxically followed by S1P1 functional antagonism, whereby receptors are internalized and degraded, thus reducing or eliminating them from the lymphocyte cell surface.40,60,70,74,75 This down-regulation renders lymphocytes unresponsive to the normal S1P gradient and thus deprives them of the obligatory signal that would ordinarily allow them to egress from lymphoid tissues and recirculate to the periphery.
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MINOR
Structure of Siponimod
CUMULATIVE EXCRETION
FECAL
Structure of Siponimod
CUMULATIVE EXCRETION
URINE
SPHINGOSINE 1-PHOSPHATE RECEPTOR 1
TARGET -> AGONIST
Blocks the capacity of lymphocytes to egress from lymph nodes, reducing the number of lymphocytes in peripheral blood.
EC50
Structure of Siponimod
EXCRETED UNCHANGED
FECAL
Structure of SIPONIMOD ADIPIC ACID
SALT/SOLVATE -> PARENT
Structure of SIPONIMOD ADIPIC ACID
SOLVATE->ANHYDROUS
CYTOCHROME P450 2C9
METABOLIC ENZYME -> SUBSTRATE
CYP2C9 genotype had a significant effect on the exposure of siponimod, with CYP2C9 *3/*3, CYP2C9 *1/*3, and CYP2C9 *2/*3 individuals having the largest effect.
MAJOR
Structure of Siponimod Fumaric Acid
SOLVATE->ANHYDROUS
Structure of Siponimod Fumaric Acid
SALT/SOLVATE -> PARENT
Structure of Siponimod
EXCRETED UNCHANGED
URINE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Related Record Type Details
Structure of 1-((2-ETHYL-4-((E)-N-((4-(3-HYDROXYCYCLOHEXYL)-3-(TRIFLUOROMETHYL)PHENYL)METHOXY)-C-METHYL-CARBONIMIDOYL)PHENYL)METHYL)AZETIDINE-3-CARBOXYLIC ACID
METABOLITE -> PARENT
PLASMA
Structure of 1-((4-ACETYL-2-ETHYL-PHENYL)METHYL)AZETIDINE-3-CARBOXYLIC ACID
METABOLITE -> PARENT
MINOR
FECAL; URINE
Structure of CHOLESTERYL SIPONIMOD
METABOLITE -> PARENT
Structure of DES(CYCLOHEXYL)-4-HYDROXYCYCLOHEXYL-SIPONIMOD GLUCORONIDE
METABOLITE -> PARENT
URINE
Structure of 1-((2-ETHYL-4-(1-HYDROXYETHYL)PHENYL)METHYL)AZETIDINE-3-CARBOXYLIC ACID
METABOLITE -> PARENT
MINOR
URINE
Structure of 1-((2-ETHYL-4-((E)-N-HYDROXY-C-METHYL-CARBONIMIDOYL)PHENYL)METHYL)AZETIDINE-3-CARBOXYLIC ACID
METABOLITE -> PARENT
MINOR
URINE
Structure of DES(CYCLOHEXYL)-4-HYDROXYCYCLOHEXYL-SIPONIMOD GLUCORONIDE
METABOLITE INACTIVE -> PARENT
MAJOR
PLASMA
Structure of DES(CYCLOHEXYL)-4-HYDROXYCYCLOHEXYL-SIPONIMOD
METABOLITE INACTIVE -> PARENT
MAJOR
FECAL; PLASMA; URINE
Related Record Type Details
Structure of Siponimod
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC IN HEALTHY MEN

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