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    Technical details about MolPort-000-884-939, learn more about the structure, uses, toxicity, action, side effects and more

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    MolPort-000-884-939

    APIs // Active Pharmaceutical Ingredients

    PRICE INFORMATION

    DOSSIERs // Finished Dosage Forms

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    DIGITAL CONTENT

    PharmaCompass

    Minakem offers CDMO services for API & HPAPI, generics, regulatory expertise, track record performance & FDA & GMP certifications.

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    2D Structure
    Also known as: 70374-39-9, Chlortenoxicam, Xefocam, Xefo, Lorcam, Lornoxicamum
    Molecular Formula
    C13H10ClN3O4S2
    Molecular Weight
    371.8  g/mol
    InChI Key
    WLHQHAUOOXYABV-UHFFFAOYSA-N
    FDA UNII
    ER09126G7A
    Lornoxicam is an orally bioavailable oxicam and non-steroidal anti-inflammatory drug (NSAID), with analgesic, anti-pyretic, anti-thrombotic and anti-inflammatory activities. Upon oral administration, lornoxicam binds to and inhibits the activity of the cyclooxygenase enzymes (COX) type 1 (COX-1) and type 2 (COX-2). This blocks COX-mediated signaling pathways, which leads to reduced prostaglandin and thromboxane production and decreased pain, fever and inflammation.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    6-chloro-4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-ylthieno[2,3-e]thiazine-3-carboxamide
    2.1.2 InChI
    InChI=1S/C13H10ClN3O4S2/c1-17-10(13(19)16-9-4-2-3-5-15-9)11(18)12-7(23(17,20)21)6-8(14)22-12/h2-6,18H,1H3,(H,15,16,19)
    2.1.3 InChI Key
    WLHQHAUOOXYABV-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C(=C(C2=C(S1(=O)=O)C=C(S2)Cl)O)C(=O)NC3=CC=CC=N3
    2.2 Other Identifiers
    2.2.1 UNII
    ER09126G7A
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Chlortenoxicam

    2. Xefocam

    2.3.2 Depositor-Supplied Synonyms

    1. 70374-39-9

    2. Chlortenoxicam

    3. Xefocam

    4. Xefo

    5. Lorcam

    6. Lornoxicamum

    7. Ro 13-9297

    8. Lornoxicamum [inn-latin]

    9. Taigalor

    10. Safem

    11. Telos

    12. Lorcam (tn)

    13. Cltx

    14. Lornoxicam (xefo)

    15. Ccris 8589

    16. Nsc-759620

    17. Ro-13-9297

    18. 6-chloro-4-hydroxy-2-methyl-1,1-dioxo-n-pyridin-2-ylthieno[2,3-e]thiazine-3-carboxamide

    19. 6-chloro-4-hydroxy-2-methyl-n-(pyridin-2-yl)-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

    20. Chebi:31783

    21. Er09126g7a

    22. Chlortenoxicam;ro 13-9297;ts110

    23. Ro-139297

    24. 2h-thieno(2,3-e)-1,2-thiazine-3-carboxamide, 6-chloro-4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

    25. 6-chloro-4-hydroxy-2-methyl-n-pyridin-2-yl-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

    26. 70374-27-5

    27. 6-chloro-4-hydroxy-2-methyl-1,1-dioxo-n-(pyridin-2-yl)-2h-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-3-carboxamide

    28. Smr000550483

    29. Lornoxicam [usan:inn:ban]

    30. Brn 1039965

    31. Unii-er09126g7a

    32. 2h-thieno[2,3-e]-1,2-thiazine-3-carboxamide, 6-chloro-4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

    33. Mfcd00866163

    34. Lornoxicam [mi]

    35. Lornoxicam [inn]

    36. Lornoxicam [jan]

    37. Lornoxicam [usan]

    38. Lornoxicam [mart.]

    39. Lornoxicam [who-dd]

    40. Schembl35101

    41. Schembl35102

    42. 6-chloro-4-hydroxy-2-methyl-n-2-pyridinyl-2h-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide

    43. 6-chloro-4-hydroxy-2-methyl-n-2-pyridyl-2h-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxide

    44. Mls001165721

    45. Mls001304721

    46. Mls006010084

    47. Lornoxicam (jan/usan/inn)

    48. Schembl1650239

    49. Chembl1569487

    50. Chembl3188235

    51. Lornoxicam, >=98% (hplc)

    52. Bdbm92331

    53. Hms2231b07

    54. Hms3264i20

    55. Hms3655n13

    56. Hms3887c17

    57. Pharmakon1600-01502302

    58. Ts110

    59. Albb-014101

    60. Bcp04666

    61. Hy-b0367

    62. Zinc5318420

    63. Nsc759620

    64. S2047

    65. Stl504715

    66. Ts-110

    67. Zinc49089868

    68. Akos000281810

    69. Akos026750113

    70. Zinc100015491

    71. Ab07518

    72. Ac-4675

    73. Bcp9000860

    74. Ccg-213023

    75. Db06725

    76. Ks-1080

    77. Nsc 759620

    78. Ncgc00246566-01

    79. Ncgc00346667-01

    80. Ncgc00346667-02

    81. 6-chloro-4-hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2h-thieno[2,3-e]-1,2-thiazine-1,1-dioxide

    82. Hn-10000

    83. Bcp0726000036

    84. Ft-0630797

    85. Ft-0670854

    86. L0239

    87. Sw220125-1

    88. C76243

    89. D01866

    90. Ab00876293_04

    91. Ab00876293_06

    92. 374l399

    93. A836864

    94. Sr-01000799148

    95. Q-101309

    96. Q2734874

    97. Sr-01000799148-3

    98. (3e)-6-chloro-3-[hydroxy(pyridin-2-ylamino)methylene]- 2-methyl-2,3-dihydro-4h-thieno[2,3-e][1,2] Thiazin- 4 - One 1,1-dioxide

    99. (3e)-6-chloro-3-[hydroxyl(pyridin-2-ylamino)methylene]-2-methyl-2,3-dihydro-4h-thieno[2,3-e][1,2]thiazin-4-one 1,1-dioxide

    100. (3z)-6-chloranyl-2-methyl-1,1-bis(oxidanylidene)-3-[oxidanyl-(pyridin-2-ylamino)methylidene]thieno[2,3-e][1,2]thiazin-4-one

    101. (3z)-6-chloro-3-[hydroxy-(2-pyridinylamino)methylidene]-2-methyl-1,1-dioxo-4-thieno[2,3-e]thiazinone

    102. 2h-thieno(3,2-e)-1,2-thiazine-3-carboxamide, 6-chloro-4-hydroxy-2-methyl-n-2-pyridinyl-, 1,1-dioxide

    103. 6-chloro-4-hydroxy-2-methyl-1,1-dioxo-n-(pyridin-2-yl)-2h-1

    104. E?-thieno[2,3-e][1,2]thiazine-3-carboxamide

    105. 6-chloro-4-hydroxy-2-methyl-n-(2-pyridyl)-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide

    106. 6-chloro-4-hydroxy-2-methyl-n-(pyridin-2-yl)-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide1,1-dioxide

    107. 6-chloro-4-hydroxy-2-methyl-n-pyridin-2-yl-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide 1,1-dioxide (lornoxicam)

    108. 6-chloro-4-hydroxy-2-methyl-n-pyridin-2-yl-2h-thieno[2,3-e][1,2]thiazine-3-carboxamide-1,1-dioxide

    2.4 Create Date
    2011-12-26
    3 Chemical and Physical Properties
    Molecular Weight 371.8 g/mol
    Molecular Formula C13H10ClN3O4S2
    XLogP32.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count2
    Exact Mass370.9801258 g/mol
    Monoisotopic Mass370.9801258 g/mol
    Topological Polar Surface Area136 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity634
    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 acute mild to moderate pain, as well as pain and inflammation of the joints caused by certain types of rheumatic diseases.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Lornoxicam is a non-steroidal anti-inflammatory drug (NSAID) that belongs to the oxicam class. As with other NSAIDS, lornoxicam is a potent inhibitor of the cyclooxgenase enzymes, which are responsible for catalyzing the formation of prostaglandins (act as messenger molecules in the process of inflammation) and thromboxane from arachidonic acid. Unlike some NSAIDS, lornoxicam's inhibition of cyclooxygenase does not lead to an increase in leukotriene formation, meaning that arachidonic acid is not moved to the 5-lipoxygenase cascade, resulting in the minimization of the risk of adverse events.

    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.)

    5.3 ATC Code

    M - Musculo-skeletal system

    M01 - Antiinflammatory and antirheumatic products

    M01A - Antiinflammatory and antirheumatic products, non-steroids

    M01AC - Oxicams

    M01AC05 - Lornoxicam

    5.4 Absorption, Distribution and Excretion

    Absorption

    Lornoxicam is absorbed rapidly and almost completely from the GI tract (90-100%).

    5.5 Metabolism/Metabolites

    Lornoxicam is metabolized completely by cyp 2C9 with the principal metabolite being 5'-hydroxy-lornoxicam and only negligible amounts of intact lornoxicam are excreted unchanged in the urine. Approximately 2/3 of the drug is eliminated via the liver and 1/3 via the kidneys in the active form.

    Lornoxicam has known human metabolites that include 5'-Hydroxylornoxicam.

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

    5.6 Biological Half-Life

    3-5 hours

    5.7 Mechanism of Action

    Like other NSAIDS, lornoxicam's anti-inflammatory and analgesic activity is related to its inhibitory action on prostaglandin and thromboxane synthesis through the inhibition of both COX-1 and COX-2. This leads to the reduction of inflammation, pain, fever, and swelling, which are mediated by prostaglandins. However, the exact mechanism of lornoxicam, like that of the other NSAIDs, has not been fully determined.

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