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    Synopsis

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    Chemistry

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    Also known as: 169590-42-5, Celebrex, Celebra, Onsenal, Celocoxib, Celecox
    Molecular Formula
    C17H14F3N3O2S
    Molecular Weight
    381.4  g/mol
    InChI Key
    RZEKVGVHFLEQIL-UHFFFAOYSA-N
    FDA UNII
    JCX84Q7J1L
    Celecoxib
    A pyrazole derivative and selective CYCLOOXYGENASE 2 INHIBITOR that is used to treat symptoms associated with RHEUMATOID ARTHRITIS; OSTEOARTHRITIS and JUVENILE ARTHRITIS, as well as the management of ACUTE PAIN.
    Celecoxib is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of celecoxib is as a Cyclooxygenase Inhibitor.
    1 2D Structure

    Celecoxib

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide
    2.1.2 InChI
    InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
    2.1.3 InChI Key
    RZEKVGVHFLEQIL-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=C(C=C1)C2=CC(=NN2C3=CC=C(C=C3)S(=O)(=O)N)C(F)(F)F
    2.2 Other Identifiers
    2.2.1 UNII
    JCX84Q7J1L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl)benzenesulfonamide

    2. Celebrex

    3. Sc 58635

    4. Sc-58635

    5. Sc58635

    2.3.2 Depositor-Supplied Synonyms

    1. 169590-42-5

    2. Celebrex

    3. Celebra

    4. Onsenal

    5. Celocoxib

    6. Celecox

    7. Sc 58635

    8. Sc-58635

    9. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide

    10. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide

    11. Ym177

    12. 184007-95-2

    13. Ym 177

    14. P-(5-p-tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamide

    15. Hsdb 7038

    16. Mfcd00941298

    17. 4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl)benzenesulfonamide

    18. Sc58635

    19. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl]benzene-1-sulfonamide

    20. Chembl118

    21. Nsc-719627

    22. Nsc-758624

    23. Dfn15

    24. Jcx84q7j1l

    25. Dfn-15

    26. 194044-54-7

    27. Chebi:41423

    28. 4-(5-(p-tolyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl)benzenesulfonamide

    29. Benzenesulfonamide, 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl]-

    30. Celecoxib [usan]

    31. Ncgc00091455-01

    32. Xilebao

    33. Dsstox_cid_2777

    34. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl]-benzenesulfonamide

    35. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonami De

    36. Dsstox_rid_76725

    37. Dsstox_gsid_22777

    38. Solexa

    39. Benzenesulfonamide, 4-(5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl)-

    40. Celebrex (tn)

    41. Smr000550473

    42. Cas-169590-42-5

    43. Sr-01000837528

    44. Ym-177

    45. Unii-jcx84q7j1l

    46. Celecoxibum

    47. Celecoxib [usan:inn:ban]

    48. Ccris 9330

    49. Tpi-336

    50. Celecoxib- Bio-x

    51. Celecoxib-[d4]

    52. Onsenal (tn)

    53. Ai-525

    54. Cep-33222

    55. Celebcoxib

    56. Elyxyb

    57. Spectrum_000432

    58. 1oq5

    59. Celecoxib [inn]

    60. Celecoxib [jan]

    61. Celecoxib [mi]

    62. Celecoxib [hsdb]

    63. Spectrum2_001576

    64. Spectrum3_001996

    65. Spectrum4_000182

    66. Spectrum5_001324

    67. Celecoxib [vandf]

    68. Celecoxib [mart.]

    69. Celecoxib [usp-rs]

    70. Celecoxib [who-dd]

    71. Cid_2662

    72. Schembl3708

    73. Celecoxib (jan/usp/inn)

    74. Bspbio_003596

    75. Celecoxib [ema Epar]

    76. Kbiogr_000723

    77. Kbiogr_002351

    78. Kbioss_000912

    79. Kbioss_002354

    80. Mls001165684

    81. Mls001195656

    82. Mls001304708

    83. Mls006011862

    84. Bidd:gt0408

    85. Divk1c_000893

    86. Spectrum1503678

    87. Spbio_001512

    88. Gtpl2892

    89. Celecoxib [orange Book]

    90. Celecoxib [ep Monograph]

    91. Celecoxib, >=98% (hplc)

    92. Dtxsid0022777

    93. Bdbm11639

    94. Hms502m15

    95. Kbio1_000893

    96. Kbio2_000912

    97. Kbio2_002351

    98. Kbio2_003480

    99. Kbio2_004919

    100. Kbio2_006048

    101. Kbio2_007487

    102. Kbio3_002830

    103. Kbio3_003037

    104. Celecoxib [usp Monograph]

    105. Ex-a175

    106. Cmap_000027

    107. Ninds_000893

    108. Bcpp000290

    109. Elyxyb (dfn-15; Oral Solution)

    110. Hms1922g14

    111. Hms2089l18

    112. Hms2093i07

    113. Hms2234n18

    114. Hms3259l08

    115. Hms3261a14

    116. Hms3373a09

    117. Hms3654h09

    118. Hms3715f11

    119. Hms3867i03

    120. Hms3884m07

    121. Pharmakon1600-01503678

    122. Consensi Component Celecoxib

    123. Act02648

    124. Albb-033772

    125. Bcp02156

    126. Zinc2570895

    127. Tox21_111135

    128. Tox21_201964

    129. Tox21_300599

    130. Tox21_500406

    131. Us8741944, Comparative Compound

    132. 4-[5-(p-tolyl)-3-(trifluoromethyl)pyrazol-1-yl]benzenesulfonamide

    133. Bbl029086

    134. Ccg-39354

    135. Nsc719627

    136. Nsc758624

    137. S1261

    138. Stl373576

    139. Celecoxib 1.0 Mg/ml In Acetonitrile

    140. Akos015842517

    141. Celecoxib Component Of Consensi

    142. Tox21_111135_1

    143. Ac-4228

    144. Am84588

    145. Bcp9000507

    146. Cs-0570

    147. Db00482

    148. Ks-1041

    149. Nc00708

    150. Nsc 719627

    151. Nsc 758624

    152. Sb19318

    153. Idi1_000893

    154. Celecoxib 100 Microg/ml In Acetonitrile

    155. Ncgc00091455-02

    156. Ncgc00091455-03

    157. Ncgc00091455-04

    158. Ncgc00091455-05

    159. Ncgc00091455-06

    160. Ncgc00091455-07

    161. Ncgc00091455-08

    162. Ncgc00091455-09

    163. Ncgc00091455-13

    164. Ncgc00254540-01

    165. Ncgc00259513-01

    166. Ncgc00261091-01

    167. Bc164295

    168. Bp-30217

    169. Hy-14398

    170. Nci60_041049

    171. Sy064976

    172. Sbi-0051875.p002

    173. Unm-0000305813

    174. Ft-0601628

    175. Ft-0623536

    176. Ft-0700357

    177. Sw199611-3

    178. A25046

    179. C07589

    180. D00567

    181. Ab00052396-07

    182. Ab00052396-08

    183. Ab00052396-09

    184. Ab00052396_10

    185. Ab00052396_11

    186. 590c425

    187. Q408801

    188. J-010566

    189. J-520011

    190. Q-200816

    191. Sr-01000837528-2

    192. Sr-01000837528-3

    193. Brd-k02637541-001-02-4

    194. Brd-k02637541-001-06-5

    195. Z2210694606

    196. Celecoxib, European Pharmacopoeia (ep) Reference Standard

    197. Celecoxib, United States Pharmacopeia (usp) Reference Standard

    198. 4-[5-(p-tolyl)-3-(trifluoromethyl)-1-pyrazolyl]benzenesulfonamide

    199. 4-(5-p-tolyl-3-(trifluoromethyl)-1h-pyrazol-1-yl)benzenesulfonamide

    200. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-pyrazol-1-yl]benzenesulfonamide

    201. 5-(4-methylphenyl)-1-(4-sulfamoylphenyl)-3-(trifluoromethyl)pyrazole

    202. Celecoxib, Pharmaceutical Secondary Standard; Certified Reference Material

    203. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyazol-1-yl]benezenesulfonamide

    204. Benzenesulfonamide,4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl]-

    205. 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-pyrazol-1-yl]benzenesulfonamide;4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1h-pyrazol-1-yl]benzenesulfonamide

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 381.4 g/mol
    Molecular Formula C17H14F3N3O2S
    XLogP33.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count3
    Exact Mass381.07588236 g/mol
    Monoisotopic Mass381.07588236 g/mol
    Topological Polar Surface Area86.4 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity577
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameCelebrex
    PubMed HealthCelecoxib (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelCELEBREX (celecoxib) is chemically designated as 4-[5-(4-methylphenyl)- 3-(trifluoromethyl)-1H-pyrazol-1-yl] benzenesulfonamide and is a diaryl-substituted pyrazole. The empirical formula is C17H14F3N3O2S, and the molecular weight is 381.38; the chem...
    Active IngredientCelecoxib
    Dosage FormCapsule
    Routeoral; Oral
    Strength200mg; 100mg; 50mg; 400mg
    Market StatusPrescription
    CompanyGd Searle

    2 of 4  
    Drug NameCelecoxib
    PubMed HealthCelecoxib (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelCELEBREX (celecoxib) is chemically designated as 4-[5-(4-methylphenyl)- 3-(trifluoromethyl)-1H-pyrazol-1-yl] benzenesulfonamide and is a diaryl-substituted pyrazole. The empirical formula is C17H14F3N3O2S, and the molecular weight is 381.38; the chem...
    Active IngredientCelecoxib
    Dosage FormCapsule
    RouteOral
    Strength200mg; 100mg; 50mg; 400mg
    Market StatusTentative Approval; Prescription
    CompanyWatson Labs; Mylan Pharms; Teva

    3 of 4  
    Drug NameCelebrex
    PubMed HealthCelecoxib (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelCELEBREX (celecoxib) is chemically designated as 4-[5-(4-methylphenyl)- 3-(trifluoromethyl)-1H-pyrazol-1-yl] benzenesulfonamide and is a diaryl-substituted pyrazole. The empirical formula is C17H14F3N3O2S, and the molecular weight is 381.38; the chem...
    Active IngredientCelecoxib
    Dosage FormCapsule
    Routeoral; Oral
    Strength200mg; 100mg; 50mg; 400mg
    Market StatusPrescription
    CompanyGd Searle

    4 of 4  
    Drug NameCelecoxib
    PubMed HealthCelecoxib (By mouth)
    Drug ClassesAnalgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent
    Drug LabelCELEBREX (celecoxib) is chemically designated as 4-[5-(4-methylphenyl)- 3-(trifluoromethyl)-1H-pyrazol-1-yl] benzenesulfonamide and is a diaryl-substituted pyrazole. The empirical formula is C17H14F3N3O2S, and the molecular weight is 381.38; the chem...
    Active IngredientCelecoxib
    Dosage FormCapsule
    RouteOral
    Strength200mg; 100mg; 50mg; 400mg
    Market StatusTentative Approval; Prescription
    CompanyWatson Labs; Mylan Pharms; Teva

    4.2 Therapeutic Uses

    Cyclooxygenase 2 Inhibitors

    National Library of Medicine's Medical Subject Headings. Celecoxib. Online file (MeSH, 2018). Available from, as of January 23, 2018: https://meshb.nlm.nih.gov/search

    /CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Celecoxib is included in the database.

    NIH/NLM; ClinicalTrials.Gov. Available from, as of January 22, 2018: https://clinicaltrials.gov/

    /Celebrex is indicated/ for the management of the signs and symptoms of osteoarthritis. /Included in US product labeling/

    NIH; DailyMed. Current Medication Information for Celebrex (Celecoxib Capsule) (Updated: October 6, 2017). Available from, as of January 24, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8d52185d-421f-4e34-8db7-f7676db2a226

    /Celebrex is indicated/ for the management of the signs and symptoms of rheumatoid arthritis. /Included in US product labeling/

    NIH; DailyMed. Current Medication Information for Celebrex (Celecoxib Capsule) (Updated: October 6, 2017). Available from, as of January 24, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=8d52185d-421f-4e34-8db7-f7676db2a226

    For more Therapeutic Uses (Complete) data for Celecoxib (14 total), please visit the HSDB record page.

    4.3 Drug Warning

    /BOXED WARNING/ WARNING: RISK OF SERIOUS CARDIOVASCULAR EVENTS. Cardiovascular Thrombotic Events: Nonsteroidal a