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Benoxaprofen

Benoxaprofen

Synopsis, Chemistry

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Also known as: 51234-28-7, Uniprofen, Oraflex, Coxigon, Opren, Inflamid

Molecular Formula

C₁₆H₁₂ClNO₃

Molecular Weight

301.72 g/mol

InChI Key

MITFXPHMIHQXPI-UHFFFAOYSA-N

FDA UNII

17SZX404IM

The use of benoxaprofen, formerly marketed as Oraflex tablets, was associated with fatal cholestatic jaundice among other serious adverse reactions. The holder of the approved application voluntarily withdrew Oraflex tablets from the market on August 5, 1982.

1 2D Structure

Benoxaprofen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid

2.1.2 InChI

InChI=1S/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)

2.1.3 InChI Key

MITFXPHMIHQXPI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C1=CC2=C(C=C1)OC(=N2)C3=CC=C(C=C3)Cl)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

17SZX404IM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Benoxaprofen, (+)-isomer

2. Benoxaprofen, (+-)-isomer

3. Benoxaprofen, (-)-isomer

4. Benoxaprofen, Ammonium Salt

5. Benoxaprofen, Monosodium Salt

6. Lrcl 3794

7. Oraflex

2.3.2 Depositor-Supplied Synonyms

1. 51234-28-7

2. Uniprofen

3. Oraflex

4. Coxigon

5. Opren

6. Inflamid

7. Dl-benoxaprofen

8. Compound 90459

9. Benoxaprofene

10. Benoxaprofenum

11. Benoxaprofeno

12. 2-(2-(4-chlorophenyl)benzo[d]oxazol-5-yl)propanoic Acid

13. Lilly 90459

14. 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic Acid

15. (+-)-benoxaprofen

16. 2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic Acid

17. (1)-2-(4-chlorophenyl)benzoxazole-5-propionic Acid

18. Nsc 299582

19. Chebi:76114

20. 5-benzoxazoleacetic Acid, 2-(4-chlorophenyl)-.alpha.-methyl-

21. Nsc-299582

22. 17szx404im

23. 2-(p-chlorophenyl)-.alpha.-methyl-5-benzoxazoleacetic Acid

24. Compd 90459

25. Nsc299582

26. 2-(2-(4-chlorophenyl)-1,3-benzoxazol-5-yl)propanoic Acid

27. Benoxaprofene [inn-french]

28. Benoxaprofenum [inn-latin]

29. Benoxaprofeno [inn-spanish]

30. 2-(p-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic Acid

31. Benoxaprofen [usan:inn:ban]

32. Lrcl 3794

33. Oraflex (tn)

34. 67434-14-4

35. Einecs 257-069-7

36. Benoxaprofen (usan/inn)

37. Brn 1085080

38. Unii-17szx404im

39. (+-)-2-(p-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic Acid

40. (rs)-benoxaprofen

41. Einecs 266-692-3

42. (+/-)-benoxaprofen

43. Benoxaprofen [mi]

44. Benoxaprofen [inn]

45. Benoxaprofen [jan]

46. Benoxaprofen [usan]

47. Schembl24413

48. Benoxaprofen [mart.]

49. Compound-90459

50. Benoxaprofen [who-dd]

51. Chembl340978

52. Dtxsid4022650

53. (+-)-2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic Acid

54. 5-benzoxazoleacetic Acid, 2-(4-chlorophenyl)-alpha-methyl, (+-)-

55. Bdbm50088388

56. Db04812

57. Da-05331

58. Hy-13568

59. Cs-0007198

60. Ft-0662523

61. Ft-0662524

62. C90147

63. D03080

64. A905882

65. Q420082

66. 2-(4-chlorophenyl)-.alpha.-methyl-5-benzoxazoleacetic Acid

67. 2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic Acid #

68. (alphar)-2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic Acid

69. (alphas)-2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic Acid

70. (+/-)-2-(p-chlorophenyl)-.alpha.-methyl-5-benzoxazoleacetic Acid

71. (.+/-.)-2-(p-chlorophenyl)-.alpha.-methyl-5-benzoxazoleacetic Acid

72. 5-benzoxazoleacetic Acid, 2-(4-chlorophenyl)-.alpha.-methyl, (.+/-.)-

73. 5-benzoxazoleacetic Acid, 2-(4-chlorophenyl)-.alpha.-methyl, (+/-)-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₂ClNO₃
Molecular Weight	301.72 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	301.0505709 g/mol
Monoisotopic Mass	301.0505709 g/mol
Topological Polar Surface Area	63.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	384
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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.)

Lipoxygenase Inhibitors

Compounds that bind to and inhibit that enzymatic activity of LIPOXYGENASES. Included under this category are inhibitors that are specific for lipoxygenase subtypes and act to reduce the production of LEUKOTRIENES. (See all compounds classified as Lipoxygenase Inhibitors.)

Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

4.2 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AE - Propionic acid derivatives

M01AE06 - Benoxaprofen