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Prestwick2_001049

Prestwick2_001049

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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

Prestwick2_001049

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 Formula	C₁₉H₂₀N₂O₃
Molecular Weight	324.4 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	324.14739250 g/mol
Monoisotopic Mass	324.14739250 g/mol
Topological Polar Surface Area	60.8 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	454
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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.

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