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Etoricoxib

Synopsis, Chemistry

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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

Etoricoxib

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 Formula	C₁₈H₁₅ClN₂O₂S
Molecular Weight	358.8 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	358.0542766 g/mol
Monoisotopic Mass	358.0542766 g/mol
Topological Polar Surface Area	68.3 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	514
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 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.