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    Technical details about Etoricoxib, learn more about the structure, uses, toxicity, action, side effects and more

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    Etoricoxib

    APIs // Active Pharmaceutical Ingredients

    PRICE INFORMATION

    INTERMEDIATES

    DOSSIERs // Finished Dosage Forms

    GLOBAL SALES INFORMATION

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    ANALYTICAL SOLUTION(s)

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    2D Structure
    Also known as: 202409-33-4, Arcoxia, Tauxib, Nucoxia, Algix, Mk-0663
    Molecular Formula
    C18H15ClN2O2S
    Molecular Weight
    358.8  g/mol
    InChI Key
    MNJVRJDLRVPLFE-UHFFFAOYSA-N
    FDA UNII
    WRX4NFY03R
    A sulfone and pyridine derivative that acts as a cyclooxygenase-2 inhibitor. It is used as a NSAID for the treatment of pain associated with RHEUMATOID ARTHRITIS and ANKYLOSING SPONDYLITIS. It is also used for the short-term treatment of moderate postoperative dental pain.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine
    2.1.2 InChI
    InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3
    2.1.3 InChI Key
    MNJVRJDLRVPLFE-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=NC=C(C=C1)C2=C(C=C(C=N2)Cl)C3=CC=C(C=C3)S(=O)(=O)C
    2.2 Other Identifiers
    2.2.1 UNII
    WRX4NFY03R
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Arcoxia

    2. L 791456

    3. L-791456

    4. L791456

    5. Mk 0663

    6. Mk-0663

    7. Mk0663

    2.3.2 Depositor-Supplied Synonyms

    1. 202409-33-4

    2. Arcoxia

    3. Tauxib

    4. Nucoxia

    5. Algix

    6. Mk-0663

    7. 5-chloro-6'-methyl-3-(4-(methylsulfonyl)phenyl)-2,3'-bipyridine

    8. Mk-663

    9. L-791456

    10. Mk 0663

    11. 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine

    12. Mk 663

    13. 2,3'-bipyridine, 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-

    14. 5-chloro-2-(6-methylpyridin-3-yl)-3-(4-methylsulfonylphenyl)pyridine

    15. Wrx4nfy03r

    16. L791456

    17. 5-chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridine

    18. Chebi:6339

    19. Chembl416146

    20. 2,3'-bipyridine, 5-chloro-6'-methyl-3-(4-(methylsulfonyl)phenyl)-

    21. 5-chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridine

    22. Ncgc00164578-01

    23. Etoricoxibe

    24. Etropain

    25. Torcoxia

    26. Etoxib

    27. 5-chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinyl

    28. Mk-0663;l-791456

    29. Dsstox_cid_26457

    30. Dsstox_rid_81631

    31. Dsstox_gsid_46457

    32. Etoricoxib [usan:inn:ban]

    33. Kingcox

    34. 5-chloro-6'-methyl-3-(4-(methylsulfonyl)-phenyl)-2,3'-bipyridine

    35. Etoricoxib [usan]

    36. Cas-202409-33-4

    37. Sr-05000001486

    38. Etoricoxib (usan/inn)

    39. Unii-wrx4nfy03r

    40. Mk0663

    41. Etoricoxibum

    42. Etoricoxib- Bio-x

    43. Etoricoxib [mi]

    44. Etoricoxib [inn]

    45. Etoricoxib [mart.]

    46. Schembl4680

    47. Etoricoxib [who-dd]

    48. Gtpl2896

    49. Dtxsid3046457

    50. Hms2090a05

    51. Hms3713p20

    52. Hms3885h14

    53. Zinc579472

    54. Amy30994

    55. Bcp06428

    56. Ex-a2642

    57. Tox21 112206

    58. Tox21_112206

    59. Bdbm50072064

    60. Etoricoxib; Mk-663; Mk-0663

    61. Mfcd06797512

    62. S4651

    63. Akos016010125

    64. Tox21_112206_1

    65. Ccg-220639

    66. Cs-1047

    67. Db01628

    68. Sb18988

    69. Ncgc00164578-02

    70. 5ch

    71. Ac-29052

    72. As-17761

    73. Bc164436

    74. Etoricoxib 100 Microg/ml In Acetonitrile

    75. Hy-15321

    76. Db-045133

    77. Ft-0602793

    78. Ft-0668437

    79. D03710

    80. Etoricoxib, Vetranal(tm), Analytical Standard

    81. Ab01275483-01

    82. 409e334

    83. A848896

    84. L001141

    85. Q631202

    86. J-013140

    87. Sr-05000001486-1

    88. Sr-05000001486-2

    89. Brd-k54770957-001-01-9

    90. Brd-k54770957-001-02-7

    91. L-791,456

    92. F2173-0490

    93. Etoricoxib, United States Pharmacopeia (usp) Reference Standard

    94. 5-chloro-3-(4-methanesulfonyl-phenyl)-6''''-methyl-[2,3'''']bipyridinyl

    95. 5-chloro-3-(4-methanesulfonyl-phenyl)-6''-methyl-[2,3'']bipyridinyl

    96. 5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine

    97. 5-chloro-3-[4-(methylsulfonyl)phenyl]-2-(2-methyl-5-pyridinyl)pyridine

    98. 5-chloro-6''-methyl-3-[4-(methylsulfonyl)phenyl]-2,3''-bipyridine

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 358.8 g/mol
    Molecular Formula C18H15ClN2O2S
    XLogP33.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass358.0542766 g/mol
    Monoisotopic Mass358.0542766 g/mol
    Topological Polar Surface Area68.3 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity514
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Etoricoxib is a COX-2 selective inhibitor (approximately 106 times more selective for COX-2 inhibition over COX-1).

    5.2 MeSH Pharmacological Classification

    Cyclooxygenase 2 Inhibitors

    A subclass of cyclooxygenase inhibitors with specificity for CYCLOOXYGENASE-2. (See all compounds classified as Cyclooxygenase 2 Inhibitors.)

    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.)

    5.3 ATC Code

    M01AH05

    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

    M - Musculo-skeletal system

    M01 - Antiinflammatory and antirheumatic products

    M01A - Antiinflammatory and antirheumatic products, non-steroids

    M01AH - Coxibs

    M01AH05 - Etoricoxib

    5.4 Absorption, Distribution and Excretion

    Absorption

    Bioavailability is 100% following oral administration.

    5.5 Metabolism/Metabolites

    Hepatic, primarily via CYP3A4.

    Etoricoxib has known human metabolites that include 6-Hydroxymethyletoricoxib and Etoricoxib 1'-N'-oxide.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.6 Biological Half-Life

    22 hours

    5.7 Mechanism of Action

    Like any other COX-2 selective inhibitor Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2), preventing production of prostaglandins (PGs) from arachidonic acid.

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