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Ponesimod

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60 US Patents, 10 US Exclusivities

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Synopsis

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Chemistry

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Also known as: 854107-55-4, Act-128800, Ponvory, 5g7akv2mkp, Chembl1096146, Act128800

Molecular Formula

C₂₃H₂₅ClN₂O₄S

Molecular Weight

461.0 g/mol

InChI Key

LPAUOXUZGSBGDU-ULCCENQXSA-N

FDA UNII

5G7AKV2MKP

Ponesimod is an orally available sphingosine-1-phosphate receptor 1 (S1PR1, S1P1) agonist that acts as a functional antagonist, with potential immunomodulating activity. Upon oral administration, ponesimod selectively binds to S1PR1 on lymphocytes and causes transient receptor activation followed by S1PR1 internalization and degradation. This results in the sequestration of lymphocytes in lymph nodes. By preventing egress of lymphocytes, ponesimod reduces both the amount of circulating peripheral lymphocytes and the infiltration of lymphocytes into target tissues. This prevents a lymphocyte-mediated immune response. S1PR1, a G-protein coupled receptor, plays a key role in lymphocyte migration from lymphoid tissues.

Ponesimod is a Sphingosine 1-phosphate Receptor Modulator. The mechanism of action of ponesimod is as a Sphingosine 1-Phosphate Receptor Modulator.

1 2D Structure

Ponesimod

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5Z)-5-[[3-chloro-4-[(2R)-2,3-dihydroxypropoxy]phenyl]methylidene]-3-(2-methylphenyl)-2-propylimino-1,3-thiazolidin-4-one

2.1.2 InChI

InChI=1S/C23H25ClN2O4S/c1-3-10-25-23-26(19-7-5-4-6-15(19)2)22(29)21(31-23)12-16-8-9-20(18(24)11-16)30-14-17(28)13-27/h4-9,11-12,17,27-28H,3,10,13-14H2,1-2H3/b21-12-,25-23?/t17-/m1/s1

2.1.3 InChI Key

LPAUOXUZGSBGDU-ULCCENQXSA-N

2.1.4 Canonical SMILES

CCCN=C1N(C(=O)C(=CC2=CC(=C(C=C2)OCC(CO)O)Cl)S1)C3=CC=CC=C3C

2.1.5 Isomeric SMILES

CCCN=C1N(C(=O)/C(=C/C2=CC(=C(C=C2)OC[C@@H](CO)O)Cl)/S1)C3=CC=CC=C3C

2.2 Other Identifiers

2.2.1 UNII

5G7AKV2MKP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-(3-chloro-4-(2,3-dihydroxy-propoxy)benzylidene)-2-propylimino-3-o-tolyl-thiazolidin-4-one

2. Act 128800

3. Act-128800

4. Act128800

5. Ponvory

2.3.2 Depositor-Supplied Synonyms

1. 854107-55-4

2. Act-128800

3. Ponvory

4. 5g7akv2mkp

5. Chembl1096146

6. Act128800

7. (2z,5z)-5-(3-chloro-4-((2r)-2,3-dihydroxypropoxy)phenylmethylidene)-3-(2-methylphenyl)-2-(propylimino)-1,3-thiazolidin-4-one

8. (5z)-5-[[3-chloro-4-[(2r)-2,3-dihydroxypropoxy]phenyl]methylidene]-3-(2-methylphenyl)-2-propylimino-1,3-thiazolidin-4-one

9. (z)-5-((z)-3-chloro-4-((r)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-(o-tolyl)thiazolidin-4-one

10. Unii-5g7akv2mkp

11. Ponesimod [inn]

12. (2z,5z)-5-(3-chloro-4-((r)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-(o-tolyl)thiazolidin-4-one

13. 4-thiazolidinone, 5-[[3-chloro-4-[(2r)-2,3-dihydroxypropoxy]phenyl]methylene]-3-(2-methylphenyl)-2-(propylimino)-, (2z,5z)-

14. Ponesimod [usan:inn]

15. 4-thiazolidinone, 5-((3-chloro-4-((2r)-2,3-dihydroxypropoxy)phenyl)methylene)-3-(2-methylphenyl)-2-(propylimino)-, (2z,5z)-

16. Act 128800

17. Ponesimod (usan/inn)

18. Ponesimod [usan]

19. Ponesimod [who-dd]

20. Ponesimod,act-128800

21. Gtpl9320

22. Ponesimod (act-128800)

23. Ponesimod [orange Book]

24. Schembl15477934

25. Schembl15477937

26. Dtxsid50234631

27. Amy23424

28. Enb-0040

29. Ex-a1417

30. Bdbm50316768

31. Mfcd18207776

32. S8241

33. Zinc34509627

34. At27979

35. Ccg-269345

36. Compound 8bo [pmid:20446681]

37. Db12016

38. Ac-30921

39. As-35140

40. Bp175283

41. Hy-10569

42. D11215

43. (2z,5z)-5-(3-chloro-4-((2r)-2,3-dihydroxypropoxy)benzylidene)-3-(2-methylphenyl)-2-(propylimino)-1,3-thiazolidin-4-one

44. (z,z)-5-[3-chloro-4-((2s)-2,3-dihydroxy-propoxy)-benzylidene]-2-propylimino-3-otolyl-thiazolidin-4-one

45. 4-thiazolidinone,5-[[3-chloro-4-[(2r)-2,3-dihydroxypropoxy]phenyl]methylene]-3-(2-methylphenyl)-2-(propylimino)-,(2z,5z)-

46. 5-(3-chloro-4-(((2r)-2,3-dihydroxypropyl)oxy)benz-(z)-ylidene)-2-((z)-propylimino)-3-(o-tolyl)thiazolidin-4-one

47. 5-(3-chloro-4-(2,3-dihydroxy-propoxy)benzylidene)-2-propylimino-3-o-tolyl-thiazolidin-4-one

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₃H₂₅ClN₂O₄S
Molecular Weight	461.0 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Exact Mass	460.1223562 g/mol
Monoisotopic Mass	460.1223562 g/mol
Topological Polar Surface Area	108 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	674
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

Ponesimod is indicated to treat adults with relapsing forms of multiple sclerosis, including clinically isolated syndrome, relapsing-remitting disease, and active secondary progressive disease.

Ponvory is indicated for the treatment of adult patients with relapsing forms of multiple sclerosis (RMS) with active disease defined by clinical or imaging features.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ponesimod is a sphingosine 1-phosphate receptor 1 modulator indicated to treat adults with relapsing forms of multiple sclerosis. It has a long duration of action as it is given once daily. Patients should be counselled about the risk of infections, bradyarrhythmia, atrioventricular conduction delays, decreased respiratory function, liver injury, increased blood pressure, cutaneous malignancies, fetal harm, and macular edema.

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 FDA Pharmacological Classification

5.3.1 Active Moiety

PONESIMOD

5.3.2 FDA UNII

5G7AKV2MKP

5.3.3 Pharmacological Classes

Sphingosine 1-phosphate Receptor Modulator [EPC]; Sphingosine 1-Phosphate Receptor Modulators [MoA]

5.4 ATC Code

L04AA

L - Antineoplastic and immunomodulating agents

L04 - Immunosuppressants

L04A - Immunosuppressants

L04AA - Selective immunosuppressants

L04AA50 - Ponesimod

5.5 Absorption, Distribution and Excretion

Absorption

A 10mg oral dose of ponesimod is 84% bioavailable. Ponesimod reaches a C_max of 109 ng/mL, with a T_max of 4.0 hours, and an AUC of 3872 h\*ng/mL.

Route of Elimination

57.3-79.6% of a radiolabelled oral dose is recovered in the feces, with 16-26% as the unmetabolized parent compound and 22% as the M12 metabolite. 10.3-18.4% of an oral dose is eliminated in the urine. 0.6-1.9% of a radiolabelled dose was recovered as expired CO₂.

Volume of Distribution

The volume of distribution of ponesimod at steady state is 160 L.

Clearance

The clearance of ponesimod is 3.8 L/h.

5.6 Metabolism/Metabolites

Ponesimod can be sulfated to the M5 metabolite, oxidized to an undefined M27 metabolite, reduced to the M6 metabolite, dealkylated to the M32 metabolite, or oxidized and hydrolyzed to the M13 metabolite. Ponesimod can also be oxidized by CYP2J2, CYP3A4, CYP3A5, CYP4F3A, and CYP4F12 to the M12 metabolite. The undefined M27 metabolite can be glucuronidated by UGT1A1 and UGT 2B7 to the M38, M39, and M40 metabolites. The M12 metabolite is either dealkylated to the M32 metabolite or oxidized and hydrolyzed to M13. M13 is dealkylated to M32, which is reduced and oxidized to M48.

5.7 Biological Half-Life

Ponesimod has an elimination half life of 33 hours.

5.8 Mechanism of Action

The sphingosine 1-phosphate receptor 1 (S1P1R) is expressed on the surface of lymphocytes and detects sphingosine 1-phosphate (S1P) at nanomolar concentrations. S1P is a metabolite of the cell membrane component, sphingomyelin. As sphingomyelin degrades, lymphocytes respond to agonism of S1P1R by concentration gradients of S1P. Lymphocytes leave the lymphoid organs in response to higher concentrations of S1P in blood and lymph. Ponesimod modulates this response by stimulating and internalizing S1P1R on lymphocytes, effectively blinding them to concentration gradients of S1P, reducing the number of lymphocytes in blood. Ponesimod is roughly 650 times more selective for S1P1R than S1P.

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