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2D Structure
Also known as: 526-08-9, Sulphaphenazole, Sulfabid, 4-amino-n-(1-phenyl-1h-pyrazol-5-yl)benzenesulfonamide, Plisulfan, Raziosulfa
Molecular Formula
C15H14N4O2S
Molecular Weight
314.4  g/mol
InChI Key
QWCJHSGMANYXCW-UHFFFAOYSA-N
FDA UNII
0J8L4V3F81

A sulfonilamide anti-infective agent.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-N-(2-phenylpyrazol-3-yl)benzenesulfonamide
2.1.2 InChI
InChI=1S/C15H14N4O2S/c16-12-6-8-14(9-7-12)22(20,21)18-15-10-11-17-19(15)13-4-2-1-3-5-13/h1-11,18H,16H2
2.1.3 InChI Key
QWCJHSGMANYXCW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)N2C(=CC=N2)NS(=O)(=O)C3=CC=C(C=C3)N
2.2 Other Identifiers
2.2.1 UNII
0J8L4V3F81
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Phenylsulfapyrazole

2. Sulfaphenylpyrazol

3. Sulphaphenazole

2.3.2 Depositor-Supplied Synonyms

1. 526-08-9

2. Sulphaphenazole

3. Sulfabid

4. 4-amino-n-(1-phenyl-1h-pyrazol-5-yl)benzenesulfonamide

5. Plisulfan

6. Raziosulfa

7. Sulfafenazol

8. Sulfaphenazol

9. Sulfaphenazon

10. Depocid

11. Depotsulfonamide

12. Sulphenazole

13. Sulfaphenylpyrazole

14. Sulfaphenylpipazol

15. Sulfaphenazolum

16. Merian

17. Sulfafenazolo

18. Eftolon

19. Firmazolo

20. Paidazolo

21. Inamil

22. Isarol

23. Orisul

24. 1-phenyl-5-sulfanilamidopyrazole

25. 5-sulfanilamido-1-phenylpyrazole

26. Microtan Pirazolo

27. N'-(1-phenylpyrazol-5-yl)sulfanilamide

28. Sulfafenazolo [italian]

29. 3-(p-aminobenzenesulfonamido)-2-phenylpyrazole

30. Sulfafenazol [inn-spanish]

31. Sulfaphenazol [inn-french]

32. Sulfaphenazolum [inn-latin]

33. Benzenesulfonamide, 4-amino-n-(1-phenyl-1h-pyrazol-5-yl)-

34. 4-amino-n-(2-phenylpyrazol-3-yl)benzenesulfonamide

35. N1-(1-phenylpyrazol-5-yl)sulfanilamide

36. N(sup 1)-(1-phenylpyrazol-5-yl)sulfanilamide

37. 4-amino-n-(1-phenyl-1h-pyrazol-5-yl)benzene-1-sulfonamide

38. Nsc-757859

39. Chembl1109

40. N(1)-(1-phenylpyrazol-5-yl)sulfanilamide

41. Chebi:77780

42. 0j8l4v3f81

43. Sulfaphenylpyrazol

44. Phenylsulfapyrazole

45. Ncgc00015925-02

46. Solfafenazolo

47. Cas-526-08-9

48. Solfafenazolo [dcit]

49. Dsstox_cid_24131

50. Dsstox_rid_80106

51. Dsstox_gsid_44131

52. Orisulf

53. Isarol V

54. Smr000326684

55. Prestwick_454

56. Unii-0j8l4v3f81

57. Sr-01000075649

58. Einecs 208-384-3

59. Lopac-s-0758

60. Sulfaphenazole (jan/inn)

61. Brn 0308518

62. Sulfonylpyrazol

63. Sulfaphenazole [inn:ban:jan]

64. Sulfabid (tn)

65. Sulfanilamide, N(sup 1)-(1-phenylpyrazol-5-yl)-

66. Mfcd00057226

67. Spectrum_001406

68. Prestwick0_000021

69. Prestwick1_000021

70. Prestwick2_000021

71. Prestwick3_000021

72. Spectrum2_001943

73. Spectrum3_001741

74. Spectrum4_000443

75. Spectrum5_001185

76. Sulfaphenazole, >=98%

77. Sulfanilamide, N1-(1-phenylpyrazol-5-yl)-

78. Sulfaphenazole [mi]

79. Sulfaphenazole [inn]

80. Sulfaphenazole [jan]

81. Lopac0_001095

82. Bspbio_000081

83. Bspbio_003442

84. Kbiogr_000826

85. Kbioss_001886

86. 5-25-09-00415 (beilstein Handbook Reference)

87. Mls000859612

88. Mls001056713

89. Divk1c_000303

90. Schembl122040

91. Spectrum1501143

92. Spbio_002002

93. Spbio_002005

94. Sulfaphenazole [mart.]

95. Bpbio1_000091

96. Sulfaphenazole [who-dd]

97. Dtxsid2044131

98. Gtpl11352

99. Hms500p05

100. Kbio1_000303

101. Kbio2_001886

102. Kbio2_004454

103. Kbio2_007022

104. Kbio3_002662

105. Zinc57490

106. 4-amino-n-(1-phenyl-1h-pyrazol-5-yl)-benzenesulfonamide

107. 4-amino-n-(2-phenyl-2h-pyrazol-3-yl)-benzenesulfonamide

108. Ninds_000303

109. Hms1568e03

110. Hms1921j13

111. Hms2095e03

112. Hms2235j21

113. Hms3263k12

114. Hms3373e16

115. Hms3712e03

116. Pharmakon1600-01501143

117. Sulfaphenazole, >=98% (hplc)

118. Albb-025160

119. Bcp27626

120. Hy-b1218

121. Str05485

122. Sulfaphenazole [orange Book]

123. Tox21_110262

124. Tox21_501095

125. Bdbm50090677

126. Ccg-39431

127. Nsc757859

128. Pyrazole, 1-phenyl-5-sulfanilamido-

129. S3673

130. Stk663863

131. Akos003348743

132. Tox21_110262_1

133. Cs-4843

134. Db06729

135. Lp01095

136. Nsc 757859

137. Sdccgsbi-0051065.p004

138. Idi1_000303

139. Ncgc00015925-01

140. Ncgc00015925-03

141. Ncgc00015925-04

142. Ncgc00015925-05

143. Ncgc00015925-06

144. Ncgc00015925-07

145. Ncgc00015925-08

146. Ncgc00015925-09

147. Ncgc00015925-10

148. Ncgc00015925-12

149. Ncgc00015925-13

150. Ncgc00015925-17

151. Ncgc00094368-01

152. Ncgc00094368-02

153. Ncgc00094368-03

154. Ncgc00094368-04

155. Ncgc00094368-05

156. Ncgc00261780-01

157. Sulfaphenazole 100 Microg/ml In Methanol

158. Sbi-0051065.p003

159. Ab00052218

160. Eu-0101095

161. Ft-0761575

162. Sulfaphenazole 100 Microg/ml In Acetonitrile

163. Bim-0051065.0001

164. D01954

165. D70410

166. S 0758

167. Ab00052218_10

168. Q6577293

169. Sr-01000075649-2

170. Sr-01000075649-7

171. Sr-01000075649-8

172. Sr-01000075649-9

173. Brd-k10671814-001-05-6

174. Brd-k10671814-001-09-8

175. 4-amino-n-(1-phenyl-1h-pyrazol-5-yl)-1-benzenesulfonamide

176. Brn-0308518; Brn0308518; Brn 0308518;sulfabid;sulfaphenylpyrazol;sulphaphenazole

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 314.4 g/mol
Molecular Formula C15H14N4O2S
XLogP31.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count4
Exact Mass314.08374688 g/mol
Monoisotopic Mass314.08374688 g/mol
Topological Polar Surface Area98.4 Ų
Heavy Atom Count22
Formal Charge0
Complexity451
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

For the treatment bacterial infections.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)


5.2 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01E - Sulfonamides and trimethoprim

J01ED - Long-acting sulfonamides

J01ED08 - Sulfaphenazole


S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AB - Sulfonamides

S01AB05 - Sulfafenazol


5.3 Metabolism/Metabolites

Hepatic.


5.4 Mechanism of Action

Sulfaphenazole is a sulfonamide antibacterial. In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis. As such, the microorganism will be "starved" of folate and die.