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    Sulindac

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    2D Structure
    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
    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

    2D Structure

    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.