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ACTIVE PHARMA INGREDIENTS

7 API Suppliers, 1 USDMF, 1 NDC API, 6 Listed Suppliers, $ API Reference Price

7 API Suppliers
1 USDMF
1 NDC API
6 Listed Suppliers
$ API Reference Price

INTERMEDIATES

3 Intermediates Suppliers

3 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

14 FDF Dossiers, 3 FDA Orange Book, 4 Europe, 2 Canada, 3 Australia, 2 South Africa

14 FDF Dossiers
3 FDA Orange Book
4 Europe
2 Canada
3 Australia
2 South Africa

DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow, 31 NEWS #PharmaBuzz

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2 DATA COMPILATION #PharmaFlow
31 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions, 4 Finished Drug Prices

globalSalesInformation
1 US Medicaid Prescriptions
4 Finished Drug Prices

MARKET PLACE

2 APIs, 2 FDF Dossiers

marketPlace
2 APIs
2 FDF Dossiers

PATENTS & EXCLUSIVITIES

9 US Patents, 6 US Exclusivities

patents
9 US Patents
6 US Exclusivities

Synopsis

ACTIVE PHARMA INGREDIENTS

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CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

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API REF. PRICE (USD/KG)

MARKET PLACE

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FDF

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

71,384,518

Annual Reports (USD Million)

Finished Drug Prices

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Chemistry

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Also known as: 1230487-00-9, Baf312 (siponimod), Mayzent, Baf-312, Siponimod [inn], Nvp-baf312-nx

Molecular Formula

C₂₉H₃₅F₃N₂O₃

Molecular Weight

516.6 g/mol

InChI Key

KIHYPELVXPAIDH-HNSNBQBZSA-N

FDA UNII

RR6P8L282I

Siponimod is 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

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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/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+

2.1.3 InChI Key

KIHYPELVXPAIDH-HNSNBQBZSA-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

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

2.2 Other Identifiers

2.2.1 UNII

RR6P8L282I

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

2.3.2 Depositor-Supplied Synonyms

1. 1230487-00-9

2. Baf312 (siponimod)

3. Mayzent

4. Baf-312

5. Siponimod [inn]

6. Nvp-baf312-nx

7. Siponimod [who-dd]

8. Baf312

9. Siponimod [usan]

10. Baf-312(siponimod)

11. 1230487-85-0

12. Rr6p8l282i

13. Chembl2336071

14. 1-((4-((1e)-1-(((4-cyclohexyl- 3-(trifluoromethyl)phenyl)methoxy)imino)ethyl)- 2-ethylphenyl)methyl)azetidine-3-carboxylic Acid

15. 3-azetidinecarboxylic Acid, 1-((4-((1e)-1-(((4-cyclohexyl-3-(trifluoromethyl)phenyl)methoxy)imino)ethyl)-2-ethylphenyl)methyl)-

16. 1-[[4-[(e)-n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic Acid

17. Unii-rr6p8l282i

18. 3-azetidinecarboxylic Acid, 1-[[4-[(1e)-1-[[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino]ethyl]-2-ethylphenyl]methyl]-

19. J8c

20. Siponimod [mi]

21. Siponimod (usan/inn)

22. Siponimod [usan:inn]

23. Schembl641699

24. Amy595

25. Baf 312

26. Dtxsid40153847

27. C29h35f3n2o3

28. (e)-1-(4-(1-(((4-cyclohexyl-3-(trifluoromethyl)benzyl)oxy)imino)ethyl)-2-ethylbenzyl)azetidine-3-carboxylic Acid

29. 1-[[4-[(~{e})-~{n}-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-~{c}-methyl-carbonimidoyl]-2-ethyl-phenyl]methyl]azetidine-3-carboxylic Acid

30. 1-{4-[1-((e)-4-cyclohexyl-3-trifluoromethyl-benzyloxyimino)-ethyl]-2-ethyl-benzyl}-azetidine-3-carboxylic Acid

31. Who 9491

32. Bdbm50428142

33. Mfcd26142651

34. Akos037645089

35. Ccg-269825

36. Cs-3876

37. Db12371

38. 1-(4-(1-((e)-4-cyclohexyl-3-trifluoromethylbenzyloxyimino)-ethyl)-2-ethylbenzyl)-azetidine-3-carboxylic Acid

39. Ac-32779

40. As-56983

41. Hy-12355

42. B3225

43. S7179

44. D11460

45. J-690082

46. (z)-4-cyano-5-((3,5-dichloropyridin-4-yl)thio)-n-(4-(methylsulfonyl)phenyl)thiophene-2-carbimidic Acid

47. 2(1h)-isoquinolinebutanoic Acid, Beta-(((4,5-dihydro-5-(2-(1h-imidazol-2-ylamino)ethyl)-3-isoxazolyl)carbonyl)amino)-3,4-dihydro-gamma-oxo-

2.4 Create Date

2010-02-01

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₅F₃N₂O₃
Molecular Weight	516.6 g/mol
XLogP3	4.8
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	516.25997747 g/mol
Monoisotopic Mass	516.25997747 g/mol
Topological Polar Surface Area	62.1 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	777
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

This drug is indicated for the treatment of relapsing forms of multiple sclerosis (MS), to include clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease in adults.

FDA Label

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 Pharmacology

**Immune system effects** Siponimod causes a dose-dependent decrease of the peripheral blood lymphocyte count within 6 hours of the first dose, caused by the reversible accumulation of lymphocytes in lymphoid tissues, due to lack of lymphocyte release. This results in a decrease in the inflammation that is involved in multiple sclerosis. Lymphocyte counts return to normal in 90% of patients within 10 days after the cessation of therapy. **Effects on heart rate and rhythm** Siponimod causes a temporary decrease in heart rate and atrioventricular conduction upon beginning treatment. The maximum fall in heart rate is observed in the first 6 hours post ingestion. Autonomic heart responses, including diurnal variation of heart rate and response to exercise activities, are not altered by siponimod treatment. **Effects on pulmonary function** Dose-dependent decreases in absolute forced expiratory volume over a time frame of 1 second were noted in siponimod-treated patients and were higher than in patients taking placebo.

5.2 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.)

5.3 ATC Code

L04

L - Antineoplastic and immunomodulating agents

L04 - Immunosuppressants

L04A - Immunosuppressants

L04AA - Selective immunosuppressants

L04AA42 - Siponimod

5.4 Absorption, Distribution and Excretion

Absorption

The time (Tmax) to attain maximum plasma concentrations (Cmax) after oral administration of immediate-release oral doses of siponimod was found to be approximately 4 hours ( with a range 3 - 8 hours). Siponimod is heavily absorbed (at a rate greater than or equal to 70%). The absolute oral bioavailability of siponimod is about 84%. Steady-state concentrations were attained after approximately 6 days of daily administration of a single dose of siponimod. **Effects of food on absorption** Food ingestion leads to delayed siponimod absorption (the median Tmax increased by approximately 2-3 hours). Food intake has no effect on the systemic exposure of siponimod (Cmax and AUC). Therefore, siponimod may be taken without regard to food.

Route of Elimination

Siponimod is eliminated from the systemic circulation mainly due to metabolism, and subsequent biliary/fecal excretion. Unchanged siponimod was not detected in urine.

Volume of Distribution

Siponimod distributes to body tissues with an average volume of distribution of 124 L. Siponimod fraction mesaured in plasma is 68% in humans. Animal studies demonstrate that siponimod readily crosses the blood-brain-barrier.

Clearance

Apparent systemic clearance of 3.11 L/h has been estimated in MS patients.

5.5 Metabolism/Metabolites

Siponimod is extensively metabolized, mainly by CYP2C9 enzyme (79.3%), and subsequently by CYP3A4 enzyme (18.5%). The pharmacological activity of the main metabolites M3 and M17 is not expected to be responsible for the clinical effect and the safety of siponimod in humans.

5.6 Biological Half-Life

The apparent elimination half-life is approximately 30 hours.

5.7 Mechanism of Action

Inflammation of the white and gray matter tissues in the central nervous system caused by localized immune cell infiltration and their cytokines are the initial cause of damage in MS. B lymphocytes and their cytokines are other factors in the pathogenesis of MS. Lymphotoxin [or transforming growth factor beta (TGF-)] and TNF- produced by these cells encourage inflammation. The S1P receptor is an important receptor related to the function of lymphocytes and can be found in the central nervous system. S1P receptor (S1PR) signaling is associated with a wide variety of physiological processes for lymphocytes, including their egress and recirculation. Siponimod is classified as a sphingosine-1-phosphate (S1P) receptor modulator. Siponimod binds with high affinity to both S1P receptors 1 and 5. This drug blocks the ability of lymphocytes to release from the lymph nodes, decreasing the number of lymphocytes found in the peripheral blood. The mechanism by which siponimod exerts therapeutic effects in multiple sclerosis is not known at this time, but may involve the abovementioned decrease of lymphocytes into the central nervous system, decreasing the inflammatory effects of MS.

API SUPPLIERS

01

Metrochem API Private Limited

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Booth #3A33

Metrochem has been delivering customized volume & quality products to customers across the world, taking utmost care of their needs.

Contact Supplier

India

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

02

Dr. Reddy\'s Laboratories

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Booth #24A41

DRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

Contact Supplier

India

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC

KDMF VMF Others AUDIT

03

Virupaksha Organics

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

CPhI Worldwide, Milan

Booth #3A97

With Virupaksha, you get a quality product with on-time delivery.

Contact Supplier

India

Virtual Booth

Digital Content

USDMF CEP/COS JDMF EU-WC NDC KDMF VMF Others AUDIT

04

Cipla

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Luxepack

Not Confirmed

05

Aurobindo Pharma Limited

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Luxepack

Not Confirmed

06

Maithri Drugs

India

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Luxepack

Not Confirmed

07

Teva API

Israel

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Luxepack

Not Confirmed

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API Reference Price

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