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Prestwick3_000029

Prestwick3_000029

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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

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

Prestwick3_000029

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 Formula	C₁₁H₁₂N₂O
Molecular Weight	188.23 g/mol
XLogP3	0.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	188.094963011 g/mol
Monoisotopic Mass	188.094963011 g/mol
Topological Polar Surface Area	23.6 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	267
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.