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    Siponimod fumarate

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: Siponimod hemifumarate, Nvp-baf312-aea, 1234627-85-0, Siponimod fumaric acid, Siponimod hemifumaric acid, Z7g02xz0m6
    Molecular Formula
    C62H74F6N4O10
    Molecular Weight
    1149.3  g/mol
    InChI Key
    JNLIKIBISICTMS-PEJBKAKVSA-N
    FDA UNII
    Z7G02XZ0M6
    Siponimod Fumarate is the fumarate salt form of siponimod, an orally bioavailable sphingosine 1-phosphate (S1P) receptor modulator, with potential anti-inflammatory and immunomodulating activities. Upon oral administration, siponimod targets and binds to S1P receptors 1 and 5 on lymphocytes. This prevents the egress of lymphocytes from lymph nodes, thereby reducing both the number of circulating peripheral lymphocytes and the infiltration of lymphocytes into target tissues, such as the central nervous system (CNS). This prevents lymphocyte-mediated immune response and may reduce inflammation. S1P plays a key role in lymphocyte migration from lymphoid tissues. Siponimod does not target S1P receptor 3, the activation of which may be responsible for adverse effects such as bradycardia associated with other S1P receptor modulators.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-but-2-enedioic acid;1-[[4-[(E)-N-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-C-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid
    2.1.2 InChI
    InChI=1S/2C29H35F3N2O3.C4H4O4/c2*1-3-21-14-23(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;5-3(6)1-2-4(7)8/h2*9-14,22,25H,3-8,15-18H2,1-2H3,(H,35,36);1-2H,(H,5,6)(H,7,8)/b2*33-19+;2-1+
    2.1.3 InChI Key
    JNLIKIBISICTMS-PEJBKAKVSA-N
    2.1.4 Canonical SMILES
    CCC1=C(C=CC(=C1)C(=NOCC2=CC(=C(C=C2)C3CCCCC3)C(F)(F)F)C)CN4CC(C4)C(=O)O.CCC1=C(C=CC(=C1)C(=NOCC2=CC(=C(C=C2)C3CCCCC3)C(F)(F)F)C)CN4CC(C4)C(=O)O.C(=CC(=O)O)C(=O)O
    2.1.5 Isomeric SMILES
    CCC1=C(C=CC(=C1)/C(=N/OCC2=CC(=C(C=C2)C3CCCCC3)C(F)(F)F)/C)CN4CC(C4)C(=O)O.CCC1=C(C=CC(=C1)/C(=N/OCC2=CC(=C(C=C2)C3CCCCC3)C(F)(F)F)/C)CN4CC(C4)C(=O)O.C(=C/C(=O)O)\C(=O)O
    2.2 Other Identifiers
    2.2.1 UNII
    Z7G02XZ0M6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(4-(1-((e)-4-cyclohexyl-3-trifluoromethylbenzyloxyimino)-ethyl)-2-ethylbenzyl)-azetidine-3-carboxylic Acid

    2. Baf-312

    3. Baf312

    4. Mayzent

    5. Siponimod

    2.3.2 Depositor-Supplied Synonyms

    1. Siponimod Hemifumarate

    2. Nvp-baf312-aea

    3. 1234627-85-0

    4. Siponimod Fumaric Acid

    5. Siponimod Hemifumaric Acid

    6. Z7g02xz0m6

    7. Siponimod Fumarate (usan)

    8. Siponimod Fumarate [usan]

    9. Siponimod Fumaric Acid (jan)

    10. Siponimod Fumaric Acid [jan]

    11. Baf-312

    12. 3-azetidinecarboxylic Acid, 1-((4-((1e)-1-(((4-cyclohexyl-3-(trifluoromethyl)phenyl)methoxy)imino)ethyl)-2-ethylphenyl)methyl)-, (2e)-2-butenedioate (2:1)

    13. Mayzent (tn)

    14. Unii-z7g02xz0m6

    15. Chembl4298150

    16. Ex-a4633

    17. Siponimod Fumarate [who-dd]

    18. Siponimod Fumarate [orange Book]

    19. Siponimod Fumaric Acid [orange Book]

    20. D11072

    21. (e)-1-(4-(1-(((4-cyclohexyl-3-(trifluoromethyl)benzyl)oxy)imino)ethyl)-2-ethylbenzyl)azetidine-3-carboxylic Acid Compound With Fumaric Acid (2:1)

    22. (e)-1-(4-(1-(((4-cyclohexyl-3-(trifluoromethyl)benzyl)oxy)imino)ethyl)-2-ethylbenzyl)azetidine-3-carboxylicacidcompoundwithfumaricacid(2:1)

    23. Bis-(1-((4-((1e)-1-(((4-cyclohexyl-3-(trifluoromethyl)phenyl)methoxy)imino)ethyl)-2-ethylphenyl)methyl)azetidine-3-carboxylic Acid) (2e)-but-2-enedioate

    2.4 Create Date
    2010-07-26
    3 Chemical and Physical Properties
    Molecular Weight 1149.3 g/mol
    Molecular Formula C62H74F6N4O10
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count20
    Rotatable Bond Count20
    Exact Mass1148.53091354 g/mol
    Monoisotopic Mass1148.53091354 g/mol
    Topological Polar Surface Area199 Ų
    Heavy Atom Count82
    Formal Charge0
    Complexity896
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count3
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count3
    4 Drug and Medication Information
    4.1 Drug Indication

    Mayzent is indicated for the treatment of adult patients with secondary progressive multiple sclerosis (SPMS) with active disease evidenced by relapses or imaging features of inflammatory activity.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Sphingosine 1 Phosphate Receptor Modulators

    Agents that affect the function of G-protein coupled SPHINGOSINE 1-PHOSPHATE RECEPTORS. Their binding to the receptors blocks lymphocyte migration and are often used as IMMUNOSUPPRESSANTS. (See all compounds classified as Sphingosine 1 Phosphate Receptor Modulators.)

    5.2 ATC Code

    L04