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Lornoxicam

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20 API Suppliers, 1 USDMF, 1 JDMF, 7 EU WC, 12 Listed Suppliers, $ API Reference Price

20 API Suppliers
1 USDMF
1 JDMF
7 EU WC
12 Listed Suppliers
$ API Reference Price

FINISHED DOSAGE FORMULATIONS

39 FDF Dossiers, 12 Europe, 7 South Africa, 20 Listed Dossiers

39 FDF Dossiers
12 Europe
7 South Africa
20 Listed Dossiers

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17 APIs
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Synopsis

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Chemistry

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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

Lornoxicam

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 Formula	C₁₃H₁₀ClN₃O₄S₂
Molecular Weight	371.8 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	2
Exact Mass	370.9801258 g/mol
Monoisotopic Mass	370.9801258 g/mol
Topological Polar Surface Area	136 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	634
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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API Reference Price

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