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Chemistry

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Also known as: Clinoril, 38194-50-2, Arthrocine, Artribid, Sulindaco, Sulindacum
Molecular Formula
C20H17FO3S
Molecular Weight
356.4  g/mol
InChI Key
MLKXDPUZXIRXEP-MFOYZWKCSA-N
FDA UNII
184SNS8VUH

Sulindac
A sulfinylindene derivative prodrug whose sulfinyl moiety is converted in vivo to an active NSAID analgesic. Specifically, the prodrug is converted by liver enzymes to a sulfide which is excreted in the bile and then reabsorbed from the intestine. This helps to maintain constant blood levels with reduced gastrointestinal side effects.
Sulindac is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of sulindac is as a Cyclooxygenase Inhibitor.
1 2D Structure

Sulindac

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(3Z)-6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic acid
2.1.2 InChI
InChI=1S/C20H17FO3S/c1-12-17(9-13-3-6-15(7-4-13)25(2)24)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
2.1.3 InChI Key
MLKXDPUZXIRXEP-MFOYZWKCSA-N
2.1.4 Canonical SMILES
CC1=C(C2=C(C1=CC3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
2.1.5 Isomeric SMILES
CC\1=C(C2=C(/C1=C\C3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
184SNS8VUH
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Aclin

2. Apo Sulin

3. Apo-sulin

4. Arthrobid

5. Arthrocine

6. Chibret

7. Clinoril

8. Copal

9. Kenalin

10. Klinoril

11. Mk 231

12. Mk-231

13. Mk231

14. Novo Sundac

15. Novo-sundac

16. Nu Sulindac

17. Nu-sulindac

18. Sulindal

2.3.2 Depositor-Supplied Synonyms

1. Clinoril

2. 38194-50-2

3. Arthrocine

4. Artribid

5. Sulindaco

6. Sulindacum

7. Aflodac

8. Sulreuma

9. Sulindac Sulfoxide

10. (z)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1h-inden-3-yl)acetic Acid

11. Mobilin

12. Cis-5-fluoro-2-methyl-1-((p-methylsulfinyl)benzylidene)indene-3-acetic Acid

13. Chebi:9352

14. (z)-5-fluoro-2-methyl-1-((p-(methylsulfinyl)phenyl)methylene)-1h-indene-3-acetic Acid

15. Cis-5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-1h-indene-3-acetic Acid

16. Mk 231

17. Mk-231

18. Nsc-757344

19. 184sns8vuh

20. Algocetil

21. Citireuma

22. Clisundac

23. Imbaral

24. Reumofil

25. Sulinol

26. Chembl15770

27. Sudac

28. 1h-indene-3-acetic Acid, 5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-, (z)-

29. 2-[(1z)-5-fluoro-1-[(4-methanesulfinylphenyl)methylidene]-2-methyl-1h-inden-3-yl]acetic Acid

30. 2-[(3z)-6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylidene]inden-1-yl]acetic Acid

31. Ncgc00015970-02

32. Cas-38194-50-2

33. Dsstox_cid_3624

34. Sulindacum [inn-latin]

35. Dsstox_rid_77117

36. Dsstox_gsid_23624

37. Sulindaco [inn-spanish]

38. Cis-sulindac

39. Sulindac (clinoril)

40. (s,z)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1h-inden-3-yl)acetic Acid

41. (z)-2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)-benzylidene)-1h-inden-3-yl)acetic Acid

42. 1h-indene-3-acetic Acid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1z)-

43. Clinoril (tn)

44. Ccris 3305

45. {(1z)-5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1h-inden-3-yl}acetic Acid

46. Sr-01000075237

47. 32004-68-5

48. Einecs 253-819-2

49. Unii-184sns8vuh

50. Brn 2951842

51. Moblilin

52. Mfcd00599589

53. (z)-2-[5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1h-inden-3-yl]acetic Acid

54. 1h-indene-3-aceticacid, 5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-, (1z)-

55. 1h-indene-3-acetic Acid, 5-fluoro-2-methyl-1-((4-(methylsulfinyl)phenyl)methylene)-, (1z)-

56. Einecs 250-893-8

57. Einecs 256-402-3

58. Sulindac [usan:usp:inn:ban:jan]

59. Tocris-1707

60. Sulindac [inci]

61. Sulindac [usan]

62. Sulindac [inn]

63. Sulindac [jan]

64. Sulindac [mi]

65. Sulindac [vandf]

66. Prestwick3_000073

67. Spectrum5_001024

68. Lopac-s-8139

69. Sulindac [mart.]

70. Sulindac [usp-rs]

71. Sulindac [who-dd]

72. S 8139

73. Sulindac, >=98.0%

74. Schembl4202

75. Schembl4203

76. 5-fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1h-indene-3-acetic Acid

77. Lopac0_001070

78. Bspbio_000285

79. Bspbio_002890

80. Mls001056554

81. Spectrum1500556

82. Sulindac (jp17/usp/inn)

83. Sulindac [orange Book]

84. Bpbio1_000315

85. Gtpl5425

86. Sulindac [ep Monograph]

87. Dtxsid4023624

88. Sulindac [usp Monograph]

89. Chebi:93811

90. Hms501o03

91. Cmap_000021

92. Hms1921c11

93. Hms2092k15

94. Hms2095o07

95. Hms2231n24

96. Hms3259k06

97. Hms3263e22

98. Hms3414n11

99. Hms3649p19

100. Hms3678n09

101. Hms3712o07

102. Hms3884k18

103. Pharmakon1600-01500556

104. Hy-b0008

105. Tox21_110270

106. Tox21_301418

107. Tox21_501070

108. Bdbm50012899

109. Bdbm50103504

110. Ccg-39264

111. Nsc757344

112. S2007

113. Akos015895412

114. Cis-5-fluoro-2-methyl-1-((p-methylsulfinyl)benzylidenyl)indene-3-acetic Acid

115. Tox21_110270_1

116. Cs-0569

117. Db00605

118. Ks-5153

119. Lp01070

120. Nc00540

121. Nsc 757344

122. Sdccgsbi-0051040.p005

123. (z)-(1)-5-fluoro-2-methyl-1-((4-(methylsulphinyl)phenyl)methylene)-1h-indene-3-acetic Acid

124. (z)-5-fluoro-2-methyl-1-[[4-(methyl-sulfinyl)phenyl]methylene]-1h-indene-3-acetic Acid

125. Idi1_000601

126. Sulindac 100 Microg/ml In Acetonitrile

127. Ncgc00015970-01

128. Ncgc00015970-03

129. Ncgc00015970-04

130. Ncgc00015970-05

131. Ncgc00015970-06

132. Ncgc00015970-07

133. Ncgc00015970-08

134. Ncgc00015970-11

135. Ncgc00025268-01

136. Ncgc00025268-02

137. Ncgc00025268-03

138. Ncgc00094349-01

139. Ncgc00094349-02

140. Ncgc00255143-01

141. Ncgc00261755-01

142. Ncgc00381714-10

143. Bp-30208

144. Bs166205

145. Ls-14757

146. Smr000326718

147. Sbi-0051040.p004

148. Sulindac, Meets Usp Testing Specifications

149. Ab00513800

150. Eu-0101070

151. Sw219748-1

152. U0099

153. C01531

154. D00120

155. Ab00052105-07

156. Ab00052105_08

157. Ab00052105_09

158. Q963093

159. J-008554

160. J-012337

161. Sr-01000075237-2

162. Sr-01000075237-3

163. Sr-01000075237-5

164. Sr-01000075237-7

165. Brd-a13946108-001-04-9

166. Brd-a13946108-001-08-0

167. Sr-01000075237-13

168. Sulindac, European Pharmacopoeia (ep) Reference Standard

169. Sulindac, United States Pharmacopeia (usp) Reference Standard

170. (z)-5-fluoro-2-methyl-1-[(p-methylsulfinyl)benzylidene]-1h-indene-3-acetic Acid

171. (z)-5-fluoro-2-methyl-1-[[4-(methylsulfinyl)-phenyl]methylene]-1h-indene-3-acetic Acid

172. {(1z)-5-fluoro-2-methyl-1-[4-(methylsulfinyl)benzylidene]-1h-indene-3-yl}acetic Acid

173. 2-[(3z)-6-fluoro-2-methyl-3-[(4-methylsulfinylphenyl)methylene]inden-1-yl]acetic Acid

174. Sulindac

175. (1z)-5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-1h-indene-3-acetic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 356.4 g/mol
Molecular Formula C20H17FO3S
XLogP33.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass356.08824374 g/mol
Monoisotopic Mass356.08824374 g/mol
Topological Polar Surface Area73.6 Ų
Heavy Atom Count25
Formal Charge0
Complexity616
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameClinoril
PubMed HealthSulindac (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelSulindac is a non-steroidal, anti-inflammatory indene derivative designated chemically as (Z)-5-fluoro-2-methyl-1- [[p-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic acid. It is not a salicylate, pyrazolone or propionic acid derivative. Sulinda...
Active IngredientSulindac
Dosage FormTablet
RouteOral
Strength200mg
Market StatusPrescription
CompanyMerck

2 of 4  
Drug NameSulindac
PubMed HealthSulindac (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientSulindac
Dosage FormTablet
RouteOral
Strength200mg; 150mg
Market StatusPrescription
CompanyEpic Pharma; Watson Labs; Mutual Pharm; Mylan; Heritage Pharms

3 of 4  
Drug NameClinoril
PubMed HealthSulindac (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Drug LabelSulindac is a non-steroidal, anti-inflammatory indene derivative designated chemically as (Z)-5-fluoro-2-methyl-1- [[p-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic acid. It is not a salicylate, pyrazolone or propionic acid derivative. Sulinda...
Active IngredientSulindac
Dosage FormTablet
RouteOral
Strength200mg
Market StatusPrescription
CompanyMerck

4 of 4  
Drug NameSulindac
PubMed HealthSulindac (By mouth)
Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
Active IngredientSulindac
Dosage FormTablet
RouteOral
Strength200mg; 150mg
Market StatusPrescription
CompanyEpic Pharma; Watson Labs; Mutual Pharm; Mylan; Heritage Pharms

4.2 Drug Indication

For acute or long-term use in the relief of signs and symptoms of osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, acute painful shoulder (acute subacromial bursitis/supraspinatus tendinitis), and acute gouty arthritis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Sulindac is a non-steroidal anti-inflammatory indene derivative, also possessing analgesic and antipyretic activities.


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.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


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 FDA Pharmacological Classification
5.3.1 Active Moiety
SULINDAC
5.3.2 FDA UNII
184SNS8VUH
5.3.3 Pharmacological Classes
Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]
5.4 ATC Code

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AB - Acetic acid derivatives and related substances

M01AB02 - Sulindac


5.5 Absorption, Distribution and Excretion

Absorption

Approximately 90% absorbed in humans following oral administration.


Route of Elimination

Sulindac is excreted in rat milk; concentrations in milk were 10 to 20% of those levels in plasma. It is not known if sulindac is excreted in human milk. Approximately 50% of the administered dose of sulindac is excreted in the urine with the conjugated sulfone metabolite accounting for the major portion. Hepatic metabolism is an important elimination pathway.


Clearance

Renal cl=68.12 +/- 27.56 mL/min [NORMAL (19-41 yrs)]


5.6 Metabolism/Metabolites

Undergoes two major biotransformations: reversible reduction to the sulfide metabolite, and irreversible oxidation to the sulfone metabolite. Sulindac and its sulfide and sulfone metabolites undergo extensive enterohepatic circulation. Available evidence indicates that the biological activity resides with the sulfide metabolite. Side chain hydroxylation and hydration of the double bond also occur.


5.7 Biological Half-Life

The mean half-life of sulindac is 7.8 hours while the mean half-life of the sulfide metabolite is 16.4 hours.


5.8 Mechanism of Action

Sulindac's exact mechanism of action is unknown. Its antiinflammatory effects are believed to be due to inhibition of both COX-1 and COX-2 which leads to the inhibition of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation.


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09-Jun-2022
09-Jul-2022
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