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Siponimod
[CAS# 1230487-00-9]

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Complete supplier list of Siponimod
Identification
Classification Biochemical >> Inhibitor >> G protein coupled receptor(GPCR & G Protein) >> S1P receptor conditioner
Name Siponimod
Synonyms 1-(4-[1-[(E)-4-Cyclohexyl-3-trifluoromethyl-benzyloxyimino]-ethyl]-2-ethyl-benzyl)-azetidine-3-carboxylic acid; BAF 312
Molecular Structure CAS # 1230487-00-9, Siponimod, 1-(4-[1-[(E)-4-Cyclohexyl-3-trifluoromethyl-benzyloxyimino]-ethyl]-2-ethyl-benzyl)-azetidine-3-carboxylic acid, BAF 312
Molecular Formula C29H35F3N2O3
Molecular Weight 516.60
CAS Registry Number 1230487-00-9
SMILES CCC1=C(C=CC(=C1)/C(=N/OCC2=CC(=C(C=C2)C3CCCCC3)C(F)(F)F)/C)CN4CC(C4)C(=O)O
Properties
Solubility Insoluble (1.7E-4 g/L) (25 ºC), Calc.*, 10 mM (DMSO) (Expl.)
Density 1.24±0.1 g/cm3 (20 ºC 760 Torr), Calc.*
Index of Refraction 1.571, Calc.*
Boiling Point 602.0±65.0 ºC (760 mmHg), Calc.*
Flash Point 317.9±34.3 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H302-H315-H320-H335    Details
Precautionary Statements P264-P270-P301+P312-P330    Details
SDS Available
up Discovory and Applicatios
Siponimod is a selective modulator of sphingosine-1-phosphate receptor subtypes 1 and 5. It was developed as a treatment for secondary progressive multiple sclerosis (SPMS) and has demonstrated efficacy in reducing the risk of disability progression. The compound was discovered through targeted medicinal chemistry efforts aimed at enhancing receptor selectivity and optimizing pharmacokinetic properties to enable central nervous system penetration.

The synthesis of siponimod involves a series of chiral transformations to ensure the desired enantiomeric purity, which is critical for its biological activity. The key step in the synthesis involves the construction of the core structure via asymmetric catalysis followed by functional group modifications to introduce the required side chains. This pathway was optimized to maximize yield and minimize impurities, resulting in a scalable process suitable for industrial production.

Siponimod's primary application lies in its use for managing SPMS, a progressive form of multiple sclerosis characterized by accumulating neurological deficits. By selectively modulating sphingosine-1-phosphate receptors, siponimod reduces lymphocyte egress from lymph nodes, thereby decreasing neuroinflammation. This mechanism helps preserve neurological function and delay the progression of disability in patients with SPMS.
Market Analysis Reports
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