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    Oxyphenbutazone

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    REF. STANDARDS & IMPURITIES

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    2D Structure
    Also known as: 129-20-4, Oxyphenylbutazone, Tandearil, Oxazolidin, Tanderil, Oxifenylbutazon
    Molecular Formula
    C19H20N2O3
    Molecular Weight
    324.4  g/mol
    InChI Key
    HFHZKZSRXITVMK-UHFFFAOYSA-N
    FDA UNII
    A7D84513GV
    A non-steroidal anti-inflammatory drug. Oxyphenbutazone eyedrops have been used abroad in the management of postoperative ocular inflammation, superficial eye injuries, and episcleritis. (From AMA, Drug Evaluations Annual, 1994, p2000) It had been used by mouth in rheumatic disorders such as ankylosing spondylitis, osteoarthritis, and rheumatoid arthritis but such use is no longer considered justified owing to the risk of severe hematological adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p27)
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
    2.1.2 InChI
    InChI=1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3
    2.1.3 InChI Key
    HFHZKZSRXITVMK-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCC1C(=O)N(N(C1=O)C2=CC=C(C=C2)O)C3=CC=CC=C3
    2.2 Other Identifiers
    2.2.1 UNII
    A7D84513GV
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Diflamil

    2. Hydroxyphenylbutazone

    3. Oxyphenylbutazone

    4. Tanderil

    2.3.2 Depositor-Supplied Synonyms

    1. 129-20-4

    2. Oxyphenylbutazone

    3. Tandearil

    4. Oxazolidin

    5. Tanderil

    6. Oxifenylbutazon

    7. Oxiphenbutazone

    8. Butapirone

    9. Crovaril

    10. Flamaril

    11. Flogitolo

    12. Flogoril

    13. Rapostan

    14. Visubutina

    15. Frabel

    16. Oxalid

    17. Oxyphenobutazone

    18. P-oxyphenylbutazone

    19. Oxi-fenibutol

    20. Neo-farmadol

    21. Artroflog

    22. Butaflogin

    23. Butanova

    24. Butazonic

    25. Butilene

    26. Californit

    27. Deflogin

    28. Etrozolidina

    29. Flanaril

    30. Floghene

    31. Flogistin

    32. Flogodin

    33. Flogostop

    34. Flopirina

    35. Idrobutazina

    36. Infammil

    37. Ipabutona

    38. Isobutazina

    39. Isobutil

    40. Offitril

    41. Oxibutol

    42. Oxybuton

    43. Oxyphentamin

    44. Pirabutina

    45. Piraflogin

    46. Poliflogil

    47. Tandacote

    48. Tandalgesic

    49. Tendearil

    50. Flogal

    51. Infamil

    52. Iridil

    53. Mysite

    54. Neofen

    55. Optimal

    56. Remazin

    57. Reumox

    58. Rumapax

    59. Telidal

    60. Valioil

    61. Metabolite I

    62. Oxazolidin-geigy

    63. P-hydroxyphenylbutazone

    64. Oxiphenbutazonum

    65. Usaf Ge-14

    66. Hydroxyphenylbutazon

    67. Oxifenbutazona

    68. Tanderal

    69. Oxyphenbutazonum

    70. Oxyphenbutazone [inn]

    71. 3,5-pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl-

    72. Oxyphenbutazone Anhydrous

    73. Bm 1

    74. 1-phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine

    75. 4-butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione

    76. 1-(p-hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione

    77. 4-butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione

    78. Suganril

    79. 4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione

    80. 4-butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine

    81. 4-butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione

    82. 1-phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-n-butylpyrazolidine

    83. 3,5-dioxo-1-phenyl-2-(p-hydroxyphenyl)-4-n-butylpyrazolidene

    84. G 27202

    85. Oxyphenyl Butazone

    86. 3,5-pyrazolidinedione, 4-butyl-1-(p-hydroxyphenyl)-2-phenyl-

    87. Mls003373849

    88. Flegmostam

    89. Oxazolioin

    90. Reunabutal

    91. Aradinum

    92. Butanora

    93. Portoril

    94. Telidac

    95. Chebi:76258

    96. Genal

    97. A7d84513gv

    98. Cinophen-n

    99. Nsc-526053

    100. Oxyphenbutazone (inn)

    101. 1-(p-hydroxyphenyl)-2-phenyl-3,5-dioxo-4-n-butylpyrazolidine

    102. Ossifenbutazone [dcit]

    103. Ab00052064_08

    104. Dsstox_cid_25291

    105. Dsstox_rid_80784

    106. Dsstox_gsid_45291

    107. Oxifenbutazona [inn-spanish]

    108. Oxyphenbutazonum [inn-latin]

    109. Ossifenbutazone

    110. Opb

    111. Ccris 6717

    112. Hsdb 3144

    113. Sr-05000001689

    114. Einecs 204-936-2

    115. 1-p-hydroxyphenyl-2-phenyl-3,5-dioxo-4-n-butylpyrazolidine

    116. Nsc 526053

    117. Brn 0307474

    118. Metabolitie

    119. Romaxin

    120. Reozon

    121. Unii-a7d84513gv

    122. Ai3-26792

    123. 3,5-pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl

    124. Ncgc00016389-01

    125. Cas-129-20-4

    126. Reozon (tn)

    127. Decanoylm-nitroaniline

    128. Oxyphenbutazone (tn)

    129. Spectrum_001073

    130. Oxyphenbutazone, Tanderil

    131. Prestwick0_001049

    132. Prestwick1_001049

    133. Prestwick2_001049

    134. Prestwick3_001049

    135. Spectrum2_000153

    136. Spectrum3_000535

    137. Spectrum4_001155

    138. Spectrum5_000998

    139. Chembl1228

    140. Oxyphenbutazone [mi]

    141. Schembl25857

    142. Bspbio_000978

    143. Bspbio_002149

    144. Kbiogr_001729

    145. Kbioss_001553

    146. Divk1c_000302

    147. Oxyphenbutazone [hsdb]

    148. Spectrum1500455

    149. Spbio_000286

    150. Spbio_002909

    151. Bpbio1_001076

    152. Dtxsid1045291

    153. Oxyphenbutazone [who-dd]

    154. Hms500p04

    155. Hy-b1355a

    156. Kbio1_000302

    157. Kbio2_001553

    158. Kbio2_004121

    159. Kbio2_006689

    160. Kbio3_001649

    161. Ninds_000302

    162. 4-butyl-1-(4-hydroxyphenyl)-2-phenyl-pyrazolidine-3,5-dione

    163. Bdbm200298

    164. Hms1571a20

    165. Hms1920d20

    166. Hms2091l20

    167. Hms2098a20

    168. Hms2236g07

    169. Hms3373b01

    170. Hms3715a20

    171. Pharmakon1600-01500455

    172. Bcp20014

    173. Tox21_110414

    174. 3,5-pyrazolidinedione, 4-butyl-1-(p-hydroxyphenyl)-2-phenyl- (van)

    175. Ccg-38944

    176. Nsc526053

    177. Nsc757261

    178. Akos024362800

    179. Tox21_110414_1

    180. Db03585

    181. Idi1_000302

    182. (+/-)-oxyphenbutazone Anhydrous

    183. Ncgc00094748-01

    184. Ncgc00094748-02

    185. Ncgc00094748-03

    186. Ncgc00094748-04

    187. Ncgc00094748-07

    188. (+/-)-oxyphenbutazone-d9(n-butyl-d9)

    189. Sbi-0051471.p003

    190. Oxyphenbutazone Anhydrous, (+/-)-

    191. 3, 4-butyl-1-(p-hydroxyphenyl)-2-phenyl-

    192. Ab00052064

    193. Cs-0013099

    194. Ft-0673468

    195. Ro-04-4410

    196. Wln: T5vnnv Ehj Br Dq & Cr & E4

    197. 3, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl-

    198. Oxyphenbutazone 4-hydroxyphenylbutazone

    199. C19494

    200. D08324

    201. G-27202

    202. G-29701

    203. J-005659

    204. Q4116192

    205. Sr-05000001689-1

    206. Sr-05000001689-3

    207. Brd-a33749298-001-05-0

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 324.4 g/mol
    Molecular Formula C19H20N2O3
    XLogP32.7
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count5
    Exact Mass324.14739250 g/mol
    Monoisotopic Mass324.14739250 g/mol
    Topological Polar Surface Area60.8 Ų
    Heavy Atom Count24
    Formal Charge0
    Complexity454
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Anti-Inflammatory Agents, Non-Steroidal; Anti-Inflammatory Agents, Topical

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    EPISCLERITIS & UVEITIS ASSOC WITH RHEUMATOID ARTHRITIS HAVE SOMETIMES BEEN TREATED SUCCESSFULLY WITH...OXYPHENBUTAZONE.

    American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 972

    ...HAS MILD URICOSURIC EFFECT IN EXPTL ANIMALS & MAN, PROBABLY ATTRIBUTABLE TO ONE OF ITS METABOLITES.

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 339

    ...HAS MILD URICOSURIC EFFECT IN EXPTL ANIMALS & MAN... URICOSURIC EFFECT RESULTS FROM DIMINISHED TUBULAR REABSORPTION OF URIC ACID. ...CAUSES SIGNIFICANT RETENTION OF SODIUM & CHLORIDE, ACCOMPANIED BY REDN IN URINE VOL... REDUCES UPTAKE OF IODINE BY THYROID GLAND...ALSO INHIBITS ENZYMES OF KREBS CYCLE... /PHENYLBUTAZONE/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 339

    For more Therapeutic Uses (Complete) data for OXYPHENBUTAZONE (7 total), please visit the HSDB record page.

    4.2 Drug Warning

    ...40-YR OLD MAN RECEIVED TOTAL DOSE OF 1 G OXYPHENBUTAZONE OVER APPROX 5 DAYS, 2 MO BEFORE ADMISSION TO HOSPITAL WITH SEVERE ANEMIA & LEUCOCYTOSIS; HE DIED ON THIRD DAY AFTER DEVELOPING THIS CONDITION.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 194

    ...WHITE-BLOOD CELL DISORDER CONCERNED 47-YR-OLD MAN WHO, 13 MO BEFORE ADMISSION WITH TEMP, HAD BEEN GIVEN 1.9 G OXYPHENBUTAZONE OVER 2-WK PERIOD. ON ADMISSION, HE WAS GIVEN 0.6 G OF DRUG; BLOOD EXAM SHOWED THAT HE HAD LEUKEMIA, OF WHICH HE DIED APPROX 4 MO LATER.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 194

    IT SHOULD ALWAYS BE TAKEN IMMEDIATELY AFTER MEALS OR WITH FULL GLASS OF MILK, TO MINIMIZE GASTRIC IRRITATION.

    Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1051

    OXYPHENBUTAZONE IS SAID TO CAUSE SOMEWHAT LESS GASTRIC IRRITATION /THAN PHENYLBUTAZONE/. ... IT SHOULD BE TAKEN IN 3 OR 4 DIVIDED PORTIONS AFTER MEALS TO LESSEN GASTRIC IRRITATION.

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 341

    For more Drug Warnings (Complete) data for OXYPHENBUTAZONE (8 total), please visit the HSDB record page.

    5 Pharmacology and Biochemistry
    5.1 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.)

    5.2 ATC Code

    M - Musculo-skeletal system

    M01 - Antiinflammatory and antirheumatic products

    M01A - Antiinflammatory and antirheumatic products, non-steroids

    M01AA - Butylpyrazolidines

    M01AA03 - Oxyphenbutazone

    M - Musculo-skeletal system

    M02 - Topical products for joint and muscular pain

    M02A - Topical products for joint and muscular pain

    M02AA - Antiinflammatory preparations, non-steroids for topical use

    M02AA04 - Oxyphenbutazone

    S - Sensory organs

    S01 - Ophthalmologicals

    S01B - Antiinflammatory agents

    S01BC - Antiinflammatory agents, non-steroids

    S01BC02 - Oxyphenbutazone

    5.3 Absorption, Distribution and Excretion

    ...OXYPHENBUTAZONE IS EXTENSIVELY BOUND TO PLASMA PROTEINS & HAS PLASMA HALF-TIME OF SEVERAL DAYS. ...ONLY SLOWLY EXCRETED IN URINE, SINCE BINDING TO PLASMA PROTEIN LIMITS...GLOMERULAR FILTRATION, &...RELATIVELY HIGH PKA, WHICH FAVORS PASSIVE REABSORPTION IN DISTAL TUBULE.

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 340

    5.4 Metabolism/Metabolites

    OXIDN OF PHENYLBUTAZONE DURING CHRONIC DOSING BY MEASURING URINARY EXCRETION OF 3 METABOLITES, OXYPHENBUTAZONE GAMMA-HYDROXYPHENBUTAZONE & P,GAMMA-HYDROXYPHENBUTAZONE DURING INFUSION OF HYDROCORTISONE SODIUM SUCCINATE IS REPORTED.

    PMID:911609 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1429144 AARBAKKE J ET AL; BR J CLIN PHARMACOL 4: 621-622 (1977)

    5.5 Biological Half-Life

    IN MAN, OXYPHENBUTAZONE HAS BIOLOGICAL HALF-LIFE OF ABOUT 2 DAYS.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V13 190

    5.6 Mechanism of Action

    ...HAS PROMINENT ANTI-INFLAMMATORY EFFECTS IN ANIMALS, & COMPARABLE EFFECTS... IN PT WITH RHEUMATOID ARTHRITIS & RELATED DISORDERS. ...INHIBITS BIOSYNTHESIS OF PROSTAGLANDINS, UNCOUPLES OXIDATIVE PHOSPHORYLATION, & INHIBITS ATP-DEPENDENT BIOSYNTHESIS OF MUCOPOLYSACCHARIDE SULFATES IN CARTILAGE. /PHENYLBUTAZONE/

    Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 339