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    Chemistry

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    Also known as: Phenazone, 60-80-0, Phenazon, Antipyrin, Analgesine, Anodynine
    Molecular Formula
    C11H12N2O
    Molecular Weight
    188.23  g/mol
    InChI Key
    VEQOALNAAJBPNY-UHFFFAOYSA-N
    FDA UNII
    T3CHA1B51H
    Phenazon
    An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)
    1 2D Structure

    Phenazon

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1,5-dimethyl-2-phenylpyrazol-3-one
    2.1.2 InChI
    InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
    2.1.3 InChI Key
    VEQOALNAAJBPNY-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=O)N(N1C)C2=CC=CC=C2
    2.2 Other Identifiers
    2.2.1 UNII
    T3CHA1B51H
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Anodynin

    2. Phenazone

    3. Pyramidone

    2.3.2 Depositor-Supplied Synonyms

    1. Phenazone

    2. 60-80-0

    3. Phenazon

    4. Antipyrin

    5. Analgesine

    6. Anodynine

    7. Anodynin

    8. Azophen

    9. Fenazone

    10. 2,3-dimethyl-1-phenyl-5-pyrazolone

    11. Antipirin

    12. Antipyrinum

    13. Phenozone

    14. Apirelina

    15. Azophene

    16. Methozin

    17. Parodyne

    18. Phenazonum

    19. Phenylone

    20. Pyrazophyl

    21. Sedatine

    22. Sedatin

    23. Dimethyloxychinizin

    24. Dimethyloxyquinazine

    25. Oxydimethylquinazine

    26. Azophenum

    27. Phenylon

    28. 3-antipyrine

    29. Fenazon [czech]

    30. Fenazona

    31. 3h-pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-

    32. Fenazona [inn-spanish]

    33. Phenazone (pharmaceutical)

    34. Fenazon

    35. 1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazol-3-one

    36. Oxydimethylquinizine

    37. 1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one

    38. 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one

    39. 1-phenyl-2,3-dimethyl-5-pyrazolone

    40. 1-phenyl-2,3-dimethylpyrazole-5-one

    41. Chebi:31225

    42. Nsc 7945

    43. Phenazone;phenazon

    44. 1,5-dimethyl-2-phenylpyrazol-3-one

    45. Phenazone [inn]

    46. T3cha1b51h

    47. Phenazone (inn)

    48. Nsc-7945

    49. 1,5-dimethyl-2-phenyl-2,3-dihydro-1h-pyrazol-3-one

    50. Cas-60-80-0

    51. Ncgc00016274-04

    52. Dsstox_cid_1117

    53. Dsstox_rid_75949

    54. Dsstox_gsid_21117

    55. Antipyrine [jan]

    56. Phenazonum [inn-latin]

    57. Smr000238140

    58. Ccris 1369

    59. Antipyrine [usp:jan]

    60. Sr-05000001566

    61. Einecs 200-486-6

    62. Unii-t3cha1b51h

    63. Antipyrien

    64. 1,2-dihydro-1,5-dimethyl-2-phenyl-3h-pyrazol-3-one; Phenazone

    65. Ai3-15293

    66. .beta.-antipyrine

    67. Prestwick_26

    68. Antipyrine Crystals

    69. Mfcd00003146

    70. Component Of Auralgan

    71. 1,5-dimethyl-2-phenyl-pyrazol-3-one

    72. Spectrum_000058

    73. Antipyrine [mi]

    74. Prestwick0_000029

    75. Prestwick1_000029

    76. Prestwick2_000029

    77. Prestwick3_000029

    78. Spectrum2_000088

    79. Spectrum3_000305

    80. Spectrum4_000152

    81. Spectrum5_000842

    82. Antipyrine [vandf]

    83. Antipyrinum [hpus]

    84. Antipyrine (jp17/usp)

    85. Epitope Id:124927

    86. Phenazone [mart.]

    87. Ec 200-486-6

    88. Phenazone [who-dd]

    89. 1,5-dimethyl-2-phenyl-1h-pyrazol-3(2h)-one

    90. Antipyrine [usp-rs]

    91. Schembl20452

    92. Bspbio_000097

    93. Bspbio_001870

    94. Kbiogr_000624

    95. Kbioss_000438

    96. Mls001331753

    97. Mls001332401

    98. Mls001332402

    99. Mls002154179

    100. Divk1c_000484

    101. Spectrum1500128

    102. Spbio_000016

    103. Spbio_002018

    104. Antipyrine, Analytical Standard

    105. Bpbio1_000107

    106. Chembl277474

    107. Phenazone [ep Impurity]

    108. Dtxsid6021117

    109. Phenazone [ep Monograph]

    110. Hms501i06

    111. Kbio1_000484

    112. Kbio2_000438

    113. Kbio2_003006

    114. Kbio2_005574

    115. Kbio3_001370

    116. Zinc61044

    117. Antipyrine [usp Impurity]

    118. Nsc7945

    119. Antipyrine, >=99.0% (rt)

    120. Ninds_000484

    121. Antipyrine [usp Monograph]

    122. Hms1568e19

    123. Hms1920e09

    124. Hms2091k09

    125. Hms2095e19

    126. Hms2272g04

    127. Hms3652c09

    128. Hms3712e19

    129. Hms3885c11

    130. Pharmakon1600-01500128

    131. Wln: T5nnvj A1 Br& E1

    132. Hy-b0171

    133. Tox21_110342

    134. Tox21_201600

    135. Tox21_303026

    136. Antipyrine, Sigma Reference Standard

    137. Bdbm50103600

    138. Ccg-38904

    139. Nsc755874

    140. S3173

    141. Stk328171

    142. 1,5-dimethyl-2-phenyl-3-pyrazolone

    143. Phenazone 100 Microg/ml In Methanol

    144. Akos000588788

    145. Tox21_110342_1

    146. Cs-2044

    147. Db01435

    148. Nsc-755874

    149. Idi1_000484

    150. Phenazone 10 Microg/ml In Acetonitrile

    151. Antipyrine, Analytical Reference Material

    152. Antipyrine, Tested According To Ph.eur.

    153. Ncgc00016274-01

    154. Ncgc00016274-02

    155. Ncgc00016274-03

    156. Ncgc00016274-05

    157. Ncgc00016274-06

    158. Ncgc00016274-07

    159. Ncgc00016274-09

    160. Ncgc00016274-10

    161. Ncgc00094591-01

    162. Ncgc00094591-02

    163. Ncgc00094591-03

    164. Ncgc00178937-01

    165. Ncgc00178937-02

    166. Ncgc00256527-01

    167. Ncgc00259149-01

    168. As-13248

    169. Sbi-0051287.p003

    170. Antipyrine, Vetec(tm) Reagent Grade, 98%

    171. D1876

    172. Ft-0609690

    173. Ft-0662246

    174. Sw196343-3

    175. A19580

    176. Bim-0051287.0001

    177. D01776

    178. H11233

    179. Propyphenazone Impurity A [ep Impurity]

    180. 1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one

    181. A936893

    182. Af-960/00437050

    183. Q415578

    184. Q-201552

    185. Sr-05000001566-1

    186. Sr-05000001566-3

    187. Brd-k46937689-001-05-1

    188. Brd-k46937689-001-08-5

    189. Z56869297

    190. 2-trideuteromethyl-3-methyl-1-phenyl-3-pyrazolin-5-one

    191. F2173-0728

    192. 1,5-dimethyl-2-phenyl-1,2-dihydro-3h-pyrazol-3-one #

    193. Phenazone, European Pharmacopoeia (ep) Reference Standard

    194. Antipyrine, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 188.23 g/mol
    Molecular Formula C11H12N2O
    XLogP30.4
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count1
    Exact Mass188.094963011 g/mol
    Monoisotopic Mass188.094963011 g/mol
    Topological Polar Surface Area23.6 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity267
    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 Indication

    Antipyrine is an analgesic often used to test effects of other drugs on liver enzymes. In combination with benzocaine in otic solutions, antipyrine is indicated for the symptomatic relief of acute otitis media arising from various etiologies.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

    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

    N - Nervous system

    N02 - Analgesics

    N02B - Other analgesics and antipyretics

    N02BB - Pyrazolones

    N02BB01 - Phenazone

    S - Sensory organs

    S02 - Otologicals

    S02D - Other otologicals

    S02DA - Analgesics and anesthetics

    S02DA03 - Phenazone

    5.4 Metabolism/Metabolites

    Antipyrine has known human metabolites that include 3-hydroxy-methylantipyrine, 4-hydroxy-antipyrine, and Norantipyrine.

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

    5.5 Mechanism of Action

    Antipyrine is thought to act primarily in the CNS, increasing the pain threshold by inhibiting both isoforms of cyclooxygenase, COX-1, COX-2, and COX-3 enzymes involved in prostaglandin (PG) synthesis.

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    08-Jan-2021
    24-Jul-2024
    KGS
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