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    Teriflunomide

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 163451-81-8, 108605-62-5, Aubagio, Flucyamide, A77 1726, Hmr1726
    Molecular Formula
    C12H9F3N2O2
    Molecular Weight
    270.21  g/mol
    InChI Key
    UTNUDOFZCWSZMS-YFHOEESVSA-N
    FDA UNII
    1C058IKG3B
    Teriflunomide is the active metabolite of leflunomide, and it acts as an immunomodulatory agent by inhibiting pyrimidine synthesis. It is marketed under the name Aubagio and is indicated for the treatment of multiple sclerosis, specifically relapsing forms. The FDA label states an important warning about the risk of hepatoxicity and teratogenicity for patients using teriflunomide.
    Teriflunomide is a Pyrimidine Synthesis Inhibitor. The mechanism of action of teriflunomide is as a Dihydroorotate Dehydrogenase Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
    2.1.2 InChI
    InChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
    2.1.3 InChI Key
    UTNUDOFZCWSZMS-YFHOEESVSA-N
    2.1.4 Canonical SMILES
    CC(=C(C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F)O
    2.1.5 Isomeric SMILES
    C/C(=C(\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O
    2.2 Other Identifiers
    2.2.1 UNII
    1C058IKG3B
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2z)-2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-2-butenamide

    2. (z)-2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-2-butenamide

    3. 2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-2-butenamide

    4. 2-hydroxyethylidene-cyanoacetic Acid-4-trifluoromethyl Anilide

    5. A 1726

    6. A 771726

    7. A-771726

    8. A77 1726

    9. A771726

    10. Aubagio

    11. Hmr-1726

    12. Hmr1726

    13. Rs 61980

    2.3.2 Depositor-Supplied Synonyms

    1. 163451-81-8

    2. 108605-62-5

    3. Aubagio

    4. Flucyamide

    5. A77 1726

    6. Hmr1726

    7. Hmr-1726

    8. (z)-2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)but-2-enamide

    9. Hmr 1726

    10. A 771726

    11. A-771726

    12. Su 20

    13. A771726

    14. Teriflunomide(random Configuration)

    15. (z)-2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]but-2-enamide

    16. A 77-1726

    17. Leflunomide Related Compound B

    18. (e/z)-teriflunomide

    19. Chebi:68540

    20. 2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-2-butenamide

    21. (2z)-2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]but-2-enamide

    22. (z)-2-cyano-alpha,alpha,alpha-trifluoro-3-hydroxy-p-crotonotoluidide

    23. 2-butenamide, 2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-, (2z)-

    24. 1c058ikg3b

    25. A77-1726

    26. Teriflunomide (usan)

    27. Teriflunomide [inn]

    28. 2-butenamide, 2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-

    29. Teriflunomide [usan]

    30. 2-cyano-3-oh-n-(4-trifluoromethylphenyl)croton Amide

    31. 2-butenamide, 2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-

    32. (z)-2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)but-2-enamide.

    33. Mfcd00910058

    34. Rs 61980

    35. Teriflunomide [usan:inn]

    36. Teriflunomida

    37. Teriflunomidum

    38. Unii-1c058ikg3b

    39. 2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-2-butenamide

    40. Malononitrilamide

    41. N-(4-trifluoromethylphenyl)-2-cyano-2-hydroxycrotonamide

    42. 2-hydroxyethylidene-cyanoacetic Acid-4-trifluoromethyl Anilide

    43. 2-butenamide, 2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-, (2z)-

    44. A 1726

    45. A26

    46. Aubagio (tn)

    47. Su-0020

    48. Leflunomide Impurity B

    49. Rs-61980

    50. Leflunomide Ep Impurity B

    51. Teriflunomide [mi]

    52. (2z)-2-[hydroxy-[4-(trifluoromethyl)anilino]methylidene]-3-oxobutanenitrile

    53. Dimethyl Aprobarbital

    54. Schembl22661

    55. Teriflunomide [vandf]

    56. Teriflunomide(a-771726)

    57. Teriflunomide, A77 1726

    58. Teriflunomide [who-dd]

    59. Gtpl6844

    60. Dtxsid80893457

    61. Leflunomide Related Compound B Rs

    62. A77 1726 (e/z) Mixture

    63. Teriflunomide [orange Book]

    64. Teriflunomide [ep Monograph]

    65. Bdbm50018011

    66. Nsc766118

    67. S4169

    68. Zinc13512456

    69. Akos015994773

    70. Ccg-267145

    71. Db08880

    72. Le-0275

    73. Nsc-766118

    74. Ncgc00263218-07

    75. Ncgc00263218-13

    76. Ac-26446

    77. Hy-110159

    78. Cs-0033021

    79. Leflunomide Impurity B [ep Impurity]

    80. Sw219377-1

    81. T3287

    82. Leflunomide-d4 Metabolite (teriflunomide-d4)

    83. D10172

    84. Leflunomide Related Compound B [usp-rs]

    85. Ab01565775_02

    86. A801897

    87. A882574

    88. J-010046

    89. Q3077133

    90. Leflunomide Related Compound B [usp Impurity]

    91. N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide

    92. N-[4-(trifluoromethyl)phenyl]-2-cyano-3-hydroxycrotonamide

    93. 2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-2z-butenamide

    94. (z)-2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-2-butenamide

    95. 163451-81-8 (z Isomer) , 108605-62-5 (e/z Mixture)

    96. 2-butenamide, 2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)-, (z)-

    97. A 77-1726;a771726;hmr1726;cas# 108605-62-5

    98. (2z)-2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]but-2-enamide (teriflunomide)

    99. 2-cyano-3-hydroxy-n-(4-(trifluoromethyl)phenyl)but-2-enamide (e/z)-mixture

    100. Leflunomide Related Compound B, United States Pharmacopeia (usp) Reference Standard

    101. A 1726, A77-1726, A771726, Flucyamide, Hmr 1726, N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxycrotoamide, Su 20

    102. Teriflunomide; Leflunomide Usp Rc B; Cyano Keto Leflunomide Impurity; N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide; 2-cyano-3-hydroxy-n-[4-(trifluoromethyl)phenyl]-2-beuteamide

    2.4 Create Date
    2011-12-26
    3 Chemical and Physical Properties
    Molecular Weight 270.21 g/mol
    Molecular Formula C12H9F3N2O2
    XLogP33.3
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count2
    Exact Mass270.06161202 g/mol
    Monoisotopic Mass270.06161202 g/mol
    Topological Polar Surface Area73.1 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity426
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 2  
    Drug NameAubagio
    PubMed HealthTeriflunomide (By mouth)
    Drug ClassesCentral Nervous System Agent, Immune Modulator
    Active IngredientTeriflunomide
    Dosage FormTablet
    RouteOral
    Strength14mg; 7mg
    Market StatusPrescription
    CompanySanofi Aventis Us

    2 of 2  
    Drug NameAubagio
    PubMed HealthTeriflunomide (By mouth)
    Drug ClassesCentral Nervous System Agent, Immune Modulator
    Active IngredientTeriflunomide
    Dosage FormTablet
    RouteOral
    Strength14mg; 7mg
    Market StatusPrescription
    CompanySanofi Aventis Us

    4.2 Drug Indication

    Used in the treatment of relapsing forms of multiple sclerosis (MS).

    FDA Label

    AUBAGIO is indicated for the treatment of adult patients and paediatric patients aged 10 years and older with relapsing remitting multiple sclerosis (MS) (please refer to section 5. 1 for important information on the population for which efficacy has been established).

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Teriflunomide is an immunomodulatory agent that decreases the amount of activated CNS lymphocytes, which results in anti-inflammatory and antiproliferative effects.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents, Non-Steroidal

    Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

    Immunosuppressive Agents

    Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    TERIFLUNOMIDE
    5.3.2 FDA UNII
    1C058IKG3B
    5.3.3 Pharmacological Classes
    Pyrimidine Synthesis Inhibitor [EPC]; Dihydroorotate Dehydrogenase Inhibitors [MoA]
    5.4 ATC Code

    L04AA31

    L04AA31

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AA - Selective immunosuppressants

    L04AA31 - Teriflunomide

    5.5 Absorption, Distribution and Excretion

    Absorption

    After oral administration of teriflunomide, maximum plasma concentrations are reached, on average, in 1-4 hours.

    Route of Elimination

    Teriflunomide is eliminated unchanged and mainly through bile. Specifically 37.5% is eliminated in the feces and 22.6% in urine.

    Volume of Distribution

    After a single intravenous dose, the volume of distribution is 11 L.

    Clearance

    After a single IV dose, teriflunomide has a total body clearance of 30.5 mL/h.

    5.6 Metabolism/Metabolites

    Teriflunomide mainly undergoes hydrolyis to minor metabolites. Other minor metabolic pathways include oxidation, N-acetylation and sulfate conjugation. Teriflunomide is not metabolized by CYP450 or flavin monoamine oxidase.

    5.7 Biological Half-Life

    The median half-life is 18 to 19 days.

    5.8 Mechanism of Action

    The exact mechanism by which teriflunomide acts in MS is not known. What is known is that teriflunomide prevents pyrimidine synthesis by inhibiting the mitochondrial enzyme dihydroorotate dehydrogenase, and this may be involved in its immunomodulatory effect in MS.