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CAS 144-83-2
PharmaCompass
CAS 144-83-2
Also known as: 144-83-2, Sulphapyridine, 2-sulfapyridine, Sulfidin, Sulfidine, 2-sulfanilamidopyridine
Molecular Formula
C11H11N3O2S
Molecular Weight
249.288  g/mol
InChI Key
GECHUMIMRBOMGK-UHFFFAOYSA-N
FDA UNII
Y5V2N1KE8U

Antibacterial, potentially toxic, used to treat certain skin diseases.
1 2D Structure

CAS 144-83-2

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-N-pyridin-2-ylbenzenesulfonamide
2.1.2 InChI
InChI=1S/C11H11N3O2S/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8H,12H2,(H,13,14)
2.1.3 InChI Key
GECHUMIMRBOMGK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N
2.2 Other Identifiers
2.2.1 UNII
Y5V2N1KE8U
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 144-83-2

2. Sulphapyridine

3. 2-sulfapyridine

4. Sulfidin

5. Sulfidine

6. 2-sulfanilamidopyridine

7. Streptosilpyridine

8. Coccoclase

9. Eubasinum

10. Piridazol

11. Pyridazol

12. Eubasin

13. Haptocil

14. Plurazol

15. 2-sulfanilylaminopyridine

16. Relbapiridina

17. Sulfapiridina

18. Sulfapyridinum

19. Pyriamid

20. Septipulmon

21. Thioseptal

22. Adiplon

23. Dagenan

24. Trianon

25. Ronin

26. 2-sulfanilamidopyridin

27. Solfapiridina

28. N-2-pyridylsulfanilamide

29. N1-2-pyridylsulfanilamide

30. 4-amino-n-pyridin-2-ylbenzenesulfonamide

31. 4-amino-n-pyridin-2-yl-benzenesulfonamide

32. N(sup 1)-2-pyridylsulfanilamide

33. 2-(p-aminobenzenesulphonamido)pyridine

34. Benzenesulfonamide, 4-amino-n-2-pyridinyl-

35. 2-sulfanilyl Aminopyridine

36. Sulphapyridin

37. 2-(4-aminobenzenesulfonamido)pyridine

38. Solfapiridina [dcit]

39. N(sup1)-pyridylsulfanilamide

40. 4-[(2-pyridylamino)sulfonyl]aniline

41. 4-(2-pyridinylsulfonyl)aniline

42. 4-amino-n-(pyridin-2-yl)benzenesulfonamide

43. M+b 693

44. Sulfapyridinum [inn-latin]

45. Sulfapiridina [inn-spanish]

46. A-499

47. 2-sulfanilamidopyridin [german]

48. N(1)-pyridylsulfanilamide

49. M + B 693

50. Unii-y5v2n1ke8u

51. M And B 693

52. Nsc 4753

53. Nsc 41791

54. Sulfanilamide, N(sup 1)-2-pyridyl-

55. N(1)-2-pyridylsulfanilamide

56. Sulfapyridine (tn)

57. M&b 693

58. 4-amino-n,2-pyridinylbenzenesulfonamide

59. Sulfanilamide, N1-2-pyridyl-

60. 4-amino-n-2-pyridinyl-benzenesulfonamide

61. Sulfapyridine [usan:inn:ban]

62. C11h11n3o2s

63. Chebi:132842

64. N'-2-pyridylsulfanilide

65. Einecs 205-642-7

66. Sulfapyridine (usp/inn)

67. Ai3-01049

68. Mls000069725

69. N1-(pyridin-2-yl)sulfanilamide

70. 4-amino-n-2-pyridinylbenzenesulfonamide

71. Nsc4753

72. 4-amino-n-(pyridin-2-yl)benzene-1-sulfonamide

73. Gechumimrbomgk-uhfffaoysa-n

74. Ao-801/41077453

75. Albb-006215

76. 4-amino-n-(2-pyridyl)benzenesulfonamide

77. Ncgc00016408-01

78. Cas-144-83-2

79. Smr000058213

80. 4-amino-n-(2-pyridinyl)benzenesulfonamide

81. Dsstox_cid_6067

82. Dsstox_rid_78003

83. Dsstox_gsid_26067

84. Wln: T6nj Bmswr Dz

85. [(4-aminophenyl)sulfonyl]-2-pyridylamine

86. Pirodazole

87. Sulfapyridin

88. Sulfapyridine [usp:inn:ban]

89. Prestwick_1015

90. N1-pyridylsulfanilamide

91. Spectrum_000996

92. Sulfapyridine (dagenan)

93. Prestwick0_000762

94. Prestwick1_000762

95. Prestwick2_000762

96. Prestwick3_000762

97. Spectrum2_001323

98. Spectrum3_001773

99. Spectrum4_000346

100. Spectrum5_001182

101. Chembl700

102. D0d4cy

103. Epitope Id:122235

104. Ac1l1k4n

105. Ac1q51xl

106. Cid_5336

107. Sulfapyridine, >=99.0%

108. Y5v2n1ke8u

109. Oprea1_344996

110. Schembl44219

111. Bspbio_000804

112. Bspbio_003265

113. Kbiogr_000751

114. Kbioss_001476

115. Divk1c_000216

116. Spectrum1500551

117. Spbio_001445

118. Spbio_002743

119. Bpbio1_000886

120. Zinc2105

121. Dtxsid3026067

122. Bdbm39340

123. Ctk3j2133

124. Gechumimrbomgk-uhfffaoysa-

125. Hms500k18

126. Kbio1_000216

127. Kbio2_001476

128. Kbio2_004044

129. Kbio2_006612

130. Kbio3_002766

131. Molport-000-883-306

132. Ninds_000216

133. 4-(2-pyridinylsulfonyl)aniline #

134. Hms1570i06

135. Hms1921c03

136. Hms2092k05

137. Hms2097i06

138. Hms2233h20

139. Hms3372n13

140. Pharmakon1600-01500551

141. Hy-b0212

142. Nsc-4753

143. Nsc41791

144. Tox21_110426

145. Anw-43071

146. Bbl007713

147. Ccg-39261

148. Ls-854

149. Mfcd00038036

150. Nsc-41791

151. Nsc757329

152. S1617

153. Sbb003154

154. Stk292439

155. 2-(p-aminobenzenesulfonamido)pyridine

156. Sulfanilamide, N1-2-pyridyl-(8ci)

157. Akos000121424

158. Tox21_110426_1

159. Cs-2157

160. Db00891

161. Hs-0063

162. M&b-693

163. Mcule-7911106459

164. Nsc-757329

165. Rtr-005667

166. Sulfanilamide, N1-2-pyridyl- (8ci)

167. Vz28286

168. Idi1_000216

169. Ks-00000g93

170. Upcmld0enat5889155:001

171. Ncgc00016408-02

172. Ncgc00016408-03

173. Ncgc00016408-04

174. Ncgc00016408-05

175. Ncgc00016408-06

176. Ncgc00016408-09

177. Ncgc00016408-10

178. Ncgc00022008-03

179. Ncgc00022008-04

180. Sulfanilamide, N1-2(1h)-pyridylidene-

181. Ac-26818

182. Ak400564

183. An-43961

184. H460

185. He003686

186. He311828

187. He311829

188. Sc-65296

189. Zb000484

190. 4-amino-n-[2-pyridyl]benzene Sulfonamide

191. 4-amino-n-2-pyridinyl- Benzenesulfonamide

192. Sbi-0051525.p003

193. 4-azanyl-n-pyridin-2-yl-benzenesulfonamide

194. Ab2000164

195. Db-042750

196. Tr-005667

197. Ab00052100

198. Bb 0258406

199. Coccoclase;eubasin;eubasinum;haptocil;dagenan

200. Ft-0631839

201. R1664

202. S0071

203. St45026614

204. Benzenesulfonamide, 4-amino-n-(2-pyridinyl)-

205. D02434

206. J10161

207. Ab00052100_14

208. Ab00052100_15

209. A808279

210. Sr-01000000207

211. Sulfapyridine, Vetranal(tm), Analytical Standard

212. I14-1461

213. Sr-01000000207-2

214. W-108148

215. Brd-k41406082-001-05-5

216. Z271004858

217. Sulfapyridine, European Pharmacopoeia (ep) Reference Standard

218. Sulfapyridine, United States Pharmacopeia (usp) Reference Standard

219. Sulfapyridine Melting Point Standard, United States Pharmacopeia (usp) Reference Standard

220. Inchi=1/c11h11n3o2s/c12-9-4-6-10(7-5-9)17(15,16)14-11-3-1-2-8-13-11/h1-8h,12h2,(h,13,14)

221. Sfy

222. Sulfapyridine Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 249.288 g/mol
Molecular Formula C11H11N3O2S
XLogP30
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass249.057 g/mol
Monoisotopic Mass249.057 g/mol
Topological Polar Surface Area93.5 A^2
Heavy Atom Count17
Formal Charge0
Complexity331
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 of dermatitis herpetiformis, benign mucous membrane pemphigoid and pyoderma gangrenosum


5 Pharmacology and Biochemistry
5.1 Pharmacology

Sulfapyridine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.


Sulfapyridine is a short-acting sulfonamide antibiotic and by-product of the non-steroidal anti-inflammatory drug sulfasalazine. Its manufacture and use were discontinued in 1990.


5.2 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.


Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin.


5.3 ATC Code

J - Antiinfectives for systemic use
J01 - Antibacterials for systemic use
J01E - Sulfonamides and trimethoprim
J01EB - Short-acting sulfonamides
J01EB04 - Sulfapyridine


5.4 Absorption, Distribution and Excretion

Absorption

Approximately 60-80%


5.5 Metabolism/Metabolites

Metabolism

Hepatic.


5.6 Biological Half-Life

6-14 hours.


5.7 Mechanism of Action

Sulfapyridine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid by means of processing the substrate para-aminobenzoic acid (PABA). Dihydropteroate synthetase activity is vital in the synthesis of folate, and folate is required for cells to make nucleic acids, such as DNA or RNA. So if DNA molecules cannot be built, the cell cannot divide.


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