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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
    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 Weight 461.0 g/mol
    Molecular Formula C23H25ClN2O4S
    XLogP34.6
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count8
    Exact Mass460.1223562 g/mol
    Monoisotopic Mass460.1223562 g/mol
    Topological Polar Surface Area108 Ų
    Heavy Atom Count31
    Formal Charge0
    Complexity674
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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 Cmax of 109 ng/mL, with a Tmax 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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    ABOUT THIS PAGE

    Ponesimod Manufacturers

    A Ponesimod manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Ponesimod, including repackagers and relabelers. The FDA regulates Ponesimod manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Ponesimod API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Ponesimod manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Ponesimod Suppliers

    A Ponesimod supplier is an individual or a company that provides Ponesimod active pharmaceutical ingredient (API) or Ponesimod finished formulations upon request. The Ponesimod suppliers may include Ponesimod API manufacturers, exporters, distributors and traders.

    click here to find a list of Ponesimod suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Ponesimod GMP

    Ponesimod Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

    PharmaCompass offers a list of Ponesimod GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Ponesimod GMP manufacturer or Ponesimod GMP API supplier for your needs.

    Ponesimod CoA

    A Ponesimod CoA (Certificate of Analysis) is a formal document that attests to Ponesimod's compliance with Ponesimod specifications and serves as a tool for batch-level quality control.

    Ponesimod CoA mostly includes findings from lab analyses of a specific batch. For each Ponesimod CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

    Ponesimod may be tested according to a variety of international standards, such as European Pharmacopoeia (Ponesimod EP), Ponesimod JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Ponesimod USP).

    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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