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Also known as: 33005-95-7, Surgam, Tiaprofensaeure, 2-(5-benzoylthiophen-2-yl)propanoic acid, Acido tiaprofenico, Acide tiaprofenique

Molecular Formula

C₁₄H₁₂O₃S

Molecular Weight

260.31 g/mol

InChI Key

GUHPRPJDBZHYCJ-UHFFFAOYSA-N

FDA UNII

1LS1T6R34C

Tiaprofenic acid is a non-steroidal anti-inflammatory drug employed in the treatment of pain, particularly arthritis pain. It belongs to the arylpropionic acid (profen) group of nonsteroidal anti-inflammatory drugs (NSAIDs).

1 2D Structure

Tiaprofenic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(5-benzoylthiophen-2-yl)propanoic acid

2.1.2 InChI

InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17)

2.1.3 InChI Key

GUHPRPJDBZHYCJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C1=CC=C(S1)C(=O)C2=CC=CC=C2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

1LS1T6R34C

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Apo-tiaprofenic

2. Fc 3001

3. Flanid

4. Novo-tiaprofenic

5. Nu-tiaprofenic

6. Pms-tiaprofenic

7. Ru 15060

8. Surgam

9. Surgam Sa

10. Tiaprofenic Acid, Calcium Salt

2.3.2 Depositor-Supplied Synonyms

1. 33005-95-7

2. Surgam

3. Tiaprofensaeure

4. 2-(5-benzoylthiophen-2-yl)propanoic Acid

5. Acido Tiaprofenico

6. Acide Tiaprofenique

7. Acidum Tiaprofenicum

8. 5-benzoyl-alpha-methyl-2-thiopheneacetic Acid

9. 2-(5-benzyl-2-thienyl)propionsaeure

10. Tiaprofen

11. Acide Tiaprofenique [inn-french]

12. Acido Tiaprofenico [inn-spanish]

13. Acidum Tiaprofenicum [inn-latin]

14. Ru 15060

15. 2-[5-(phenylcarbonyl)-2-thienyl]propanoic Acid

16. Fc 3001

17. Tiaprofenate

18. Suralgan

19. Alpha-methyl-5-benzoyl-2-thienylacetic Acid

20. Chebi:32221

21. 5-benzoyl-alpha-methylthiophene-2-acetic Acid

22. 2-(5-benzoyl-2-thienyl)propanoic Acid

23. 1ls1t6r34c

24. Ru-15060

25. 2-(5-benzoyl-thiophen-2-yl)-propionic Acid

26. Dsstox_cid_3665

27. 5-benzoyl-.alpha.-methyl-2-thiopheneacetic Acid

28. Dsstox_rid_77134

29. Dsstox_gsid_23665

30. Surgam Sa

31. Einecs 251-329-3

32. Brn 1380662

33. Unii-1ls1t6r34c

34. Ncgc00016815-01

35. Prestwick_814

36. Cas-33005-95-7

37. 2-(5-benzoylthiophen-2-yl)propanoicacid

38. Prestwick0_000496

39. Prestwick1_000496

40. Prestwick2_000496

41. Prestwick3_000496

42. Epitope Id:131796

43. 2-thiopheneacetic Acid, 5-benzoyl-alpha-methyl-

44. Schembl25639

45. Bspbio_000391

46. 2-thiopheneacetic Acid, 5-benzoyl-.alpha.-methyl-

47. 5-18-08-00405 (beilstein Handbook Reference)

48. Mls002153845

49. Tiaprofenic Acid [mi]

50. Spbio_002312

51. Tiaprofenic Acid [inn]

52. Tiaprofenic Acid [jan]

53. Bpbio1_000431

54. Chembl365795

55. Dtxsid5023665

56. Tiaprofenic Acid [mart.]

57. Tiaprofenic Acid [who-dd]

58. Bdbm223313

59. Hms1569d13

60. Hms2096d13

61. Hms2230e19

62. Hms3372d06

63. Hms3713d13

64. Amy17789

65. Ex-a4101

66. Tox21_110627

67. Mfcd00866089

68. S5661

69. Stl454339

70. (5-benzoyl-2-thienyl)-propionic Acid

71. Akos015969058

72. Tiaprofenic Acid [ep Impurity]

73. Tox21_110627_1

74. Ac-8970

75. Ccg-220496

76. Db01600

77. Tiaprofenic Acid [ep Monograph]

78. Ncgc00179573-03

79. As-77449

80. Smr001233207

81. 2-(5-benzoyl-2-thienyl)propanoic Acid #

82. 2-(5-benzoylthiophen-2-yl)propionic Acid

83. Alpha-(5-benzoyl-2-thienyl)propionic Acid

84. 5-benzoyl-

85. A-methyl-2-thiopheneacetic Acid

86. Hy-106579

87. Cs-0026096

88. Ft-0675220

89. T3175

90. D01325

91. 005t957

92. Q419926

93. Sr-01000841193

94. 2-(5-benzoyl-2-thienyl)propanoic Acid, Aldrichcpr

95. 2-[5-(phenylcarbonyl)thiophen-2-yl]propanoic Acid

96. J-018971

97. Sr-01000841193-2

98. Brd-a72988804-001-03-8

99. Ethyl( Inverted Exclamation Marka)-1-[1-(4-fluorophenyl)ethyl]-1h-imidazole-4-carboxylate

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₂O₃S
Molecular Weight	260.31 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	260.05071541 g/mol
Monoisotopic Mass	260.05071541 g/mol
Topological Polar Surface Area	82.6 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	323
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 Drug and Medication Information

4.1 Drug Indication

Tiaprofenic acid is used to treat pain, especially arthritic pain.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Tiaprofenic acid is a non-steroidal anti-inflammatory drug of the arylpropionic acid (profen) class, used to treat pain, especially arthritic pain. The typical adult dose is 300mg twice daily. This drug is not recommended for use in the pediatric population.

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

M01AE - Propionic acid derivatives

M01AE11 - Tiaprofenic acid

5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability is 90% following oral administration.

5.5 Metabolism/Metabolites

Hepatic (10%). Sparingly metabolised in the liver to two inactive metabolites.

5.6 Biological Half-Life

1.5-2.5 hours

5.7 Mechanism of Action

Tiaprofenic acid belongs to a group of medicines called non-steroidal anti-inflammatory drugs (NSAIDs). It works by blocking the production of a chemical (prostaglandin) which the body produces in response to injury or certain diseases. This prostaglandin would otherwise go on to cause swelling, pain and inflammation.

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