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

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2D Structure
1. 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

2D Structure

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 Weight 301.72 g/mol
Molecular Formula C16H12ClNO3
XLogP34.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass301.0505709 g/mol
Monoisotopic Mass301.0505709 g/mol
Topological Polar Surface Area63.3 Ų
Heavy Atom Count21
Formal Charge0
Complexity384
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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


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