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Siponimod Fumarate

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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

Siponimod fumarate

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 Formula	C₆₂H₇₄F₆N₄O₁₀
Molecular Weight	1149.3 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	20
Exact Mass	1148.53091354 g/mol
Monoisotopic Mass	1148.53091354 g/mol
Topological Polar Surface Area	199 Å²
Heavy Atom Count	82
Formal Charge	0
Complexity	896
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	3
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

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

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