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2-[4-(Thiophene-2-carbonyl)-phenyl]-propionic Acid

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ACTIVE PHARMA INGREDIENTS

3 API Suppliers, 3 USDMF

3 API Suppliers
3 USDMF

FINISHED DOSAGE FORMULATIONS

1 FDF Dossiers, 1 FDA Orange Book

1 FDF Dossiers
1 FDA Orange Book

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1 USP , 1 Others

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1 USP
1 Others

Synopsis

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Chemistry

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Also known as: 40828-46-4, Profenal, Sutoprofen, Suprol, P-2-thenoylhydratropic acid, Maldocil

Molecular Formula

C₁₄H₁₂O₃S

Molecular Weight

260.31 g/mol

InChI Key

MDKGKXOCJGEUJW-UHFFFAOYSA-N

FDA UNII

988GU2F9PE

An IBUPROFEN-type anti-inflammatory analgesic and antipyretic. It inhibits prostaglandin synthesis and has been proposed as an anti-arthritic.

1 2D Structure

Suprofen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid

2.1.2 InChI

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

2.1.3 InChI Key

MDKGKXOCJGEUJW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C1=CC=C(C=C1)C(=O)C2=CC=CS2)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

988GU2F9PE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. R 25061

2. R-25061

3. R25061

4. Tn 762

5. Tn-762

6. Tn762

2.3.2 Depositor-Supplied Synonyms

1. 40828-46-4

2. Profenal

3. Sutoprofen

4. Suprol

5. P-2-thenoylhydratropic Acid

6. Maldocil

7. Masterfen

8. Sulproltin

9. Suprofenum

10. Srendam

11. Suprofene

12. Topalgic

13. Suprocil

14. Suprofene [inn-french]

15. Suprofenum [inn-latin]

16. 4-(2-thenoyl)hydratropsaeure

17. Tn-762

18. 2-[4-(thiophene-2-carbonyl)phenyl]propanoic Acid

19. 2-(4-(2-thenoyl)phenyl)propionsaeure

20. Racemic Suprofen

21. P-(2-thenoyl)hydratropic Acid

22. Tn 762

23. R-25,061

24. Alpha-methyl-4-(2-thienylcarbonyl)benzeneacetic Acid

25. (+-)-2-(p-(2-thenoyl)phenyl)propionic Acid

26. Suprofen (profenal)

27. R 25061

28. R-25061

29. 2-(4-(thiophene-2-carbonyl)phenyl)propanoic Acid

30. Nsc 303611

31. Chebi:9362

32. Hydratropic Acid, P-(2-thenoyl)-

33. Benzeneacetic Acid, .alpha.-methyl-4-(2-thienylcarbonyl)-

34. Chembl956

35. Nsc-303611

36. 988gu2f9pe

37. 2-[4-(thiophen-2-ylcarbonyl)phenyl]propanoic Acid

38. Nsc303611

39. Dsstox_cid_25469

40. Dsstox_rid_80900

41. Dsstox_gsid_45469

42. 2-[4-(thiophene-2-carbonyl)-phenyl]-propionic Acid

43. .alpha.-methyl-4-(2-thienylcarbonyl)benzeneacetic Acid

44. Dolasteron

45. Profenol

46. Profenal (tn)

47. (+/-)-suprofen

48. Sr-05000001776

49. Einecs 255-096-9

50. Suprofen (jan/usp/inn)

51. Unii-988gu2f9pe

52. Tyn-762p

53. Ncgc00016846-01

54. Prestwick_131

55. Cas-40828-46-4

56. Suprofen [usan:usp:inn:ban:jan]

57. Benzeneacetic Acid, Alpha-methyl-4-(2-thienylcarbonyl)-

58. Spectrum_001157

59. Suprofen [usan]

60. Suprofen [inn]

61. Suprofen [jan]

62. Suprofen [mi]

63. Suprofen [vandf]

64. (.+/-.)-suprofen

65. Prestwick0_000816

66. Prestwick1_000816

67. Prestwick2_000816

68. Prestwick3_000816

69. Spectrum2_001430

70. Spectrum3_000928

71. Spectrum4_001027

72. Spectrum5_001103

73. Suprofen [mart.]

74. Epitope Id:131797

75. Suprofen [usp-rs]

76. Suprofen [who-dd]

77. 2-(4-(2-thienylcarbonyl)phenyl)propanoic Acid

78. Schembl23792

79. Bspbio_000711

80. Kbiogr_001553

81. Kbioss_001637

82. Mls002154015

83. Divk1c_000476

84. Spectrum1501161

85. Spbio_001540

86. Spbio_002632

87. Suprofen [orange Book]

88. 4-(2-thenoyl)hydratropic Acid

89. Bpbio1_000783

90. Gtpl7298

91. Suprofen [usp Impurity]

92. Suprofen, >=98% (hplc)

93. Dtxsid5045469

94. Hms501h18

95. Kbio1_000476

96. Kbio2_001637

97. Kbio2_004205

98. Kbio2_006773

99. Kbio3_001936

100. Ninds_000476

101. Hms1570d13

102. Hms1921l19

103. Hms2092j07

104. Hms2097d13

105. Hms2232o08

106. Hms3372b18

107. Hms3651o17

108. Hms3714d13

109. Hms3884o08

110. Para-(2-thenoyl) Hydratropic Acid

111. Pharmakon1600-01501161

112. A-(p-thenoylphenyl) Propionic Acid

113. Hy-b0270

114. (+)-p-(2-thenoyl)hydratropic Acid

115. (-)-p-(2-thenoyl)hydratropic Acid

116. Tox21_110643

117. Bdbm50090676

118. Ccg-38977

119. Mfcd00079572

120. Nsc757876

121. S1761

122. Akos004909426

123. Tox21_110643_1

124. Ac-4551

125. Db00870

126. Nsc-757876

127. Idi1_000476

128. Ncgc00094916-01

129. Ncgc00094916-02

130. Ncgc00094916-03

131. Ncgc00094916-06

132. Ncgc00094916-09

133. As-15879

134. Smr001233343

135. Db-049665

136. Ab00052231

137. Ft-0630615

138. Sw196442-3

139. U0138

140. C07320

141. D00452

142. (+/-)-2-(p-(2-thenoyl)phenyl)propionic Acid

143. Ab00052231_08

144. (.+/-.)-2-(p-(2-thenoyl)phenyl)propionic Acid

145. 2-[4-(2-thienylcarbonyl)phenyl]propanoic Acid #

146. 828s464

147. Q3978097

148. Sr-05000001776-1

149. Sr-05000001776-3

150. 2-{4-[(thiophen-2-yl)carbonyl]phenyl}propanoic Acid

151. Brd-a34006693-001-04-8

152. Brd-a34006693-001-07-1

153. Suprofen, United States Pharmacopeia (usp) Reference Standard

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	321
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

Used as eye drops to inhibit the miosis (pupil constriction) that may occur during ocular surgery.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Suprofen is a non-steroidal anti-inflammatory analgesic and antipyretic. Ophthalmic anti-inflammatory medicines are used in the eye to lessen problems that can occur during or after some kinds of eye surgery. Sometimes, the pupil of the eye gets smaller during an operation (pupil constriction), making it more difficult for the surgeon to reach some areas of the eye. Suprofen is used to help prevent this.

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.)

Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)

5.3 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AE - Propionic acid derivatives

M01AE07 - Suprofen

5.4 Metabolism/Metabolites

Primarily hepatic (mainly via cytochrome P450 isozyme 2C9).

Suprofen has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[2-[4-(thiophene-2-carbonyl)phenyl]propanoyloxy]oxane-2-carboxylic acid, Suprofen -sulfoxide, and Thiophene-4,5-epoxide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.5 Mechanism of Action

Suprofen binds to the cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2) isoenzymes, preventing the synthesis of prostaglandins and reducing the inflammatory response. Cyclooxygenase catalyses the formation of prostaglandins and thromboxane from arachidonic acid (itself derived from the cellular phospholipid bilayer by phospholipase A₂). Prostaglandins act (among other things) as messenger molecules in the process of inflammation. The overall result is a reduction in pain and inflammation in the eyes and the prevention of pupil constriction during surgery. Normally trauma to the anterior segment of the eye (especially the iris) increases endogenous prostaglandin synthesis which leads to constriction of the iris sphincter.

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