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Chemistry

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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
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 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


USDMF

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01

SupplySide West 2024
Not Confirmed

01

SupplySide West 2024
Not Confirmed

GDUFA

DMF Review : Complete

Rev. Date : 2022-12-16

Pay. Date : 2022-11-15

DMF Number : 37679

Submission : 2022-11-16

Status : Active

Type : II

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02

SupplySide West 2024
Not Confirmed

02

SupplySide West 2024
Not Confirmed

GDUFA

DMF Review : Complete

Rev. Date : 2022-12-22

Pay. Date : 2022-11-10

DMF Number : 36596

Submission : 2021-12-09

Status : Active

Type : II

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