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Chemistry

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Also known as: 144-83-2, Sulphapyridine, 2-sulfapyridine, Sulfidin, Sulfidine, 2-sulfanilamidopyridine

Molecular Formula

C₁₁H₁₁N₃O₂S

Molecular Weight

249.29 g/mol

InChI Key

GECHUMIMRBOMGK-UHFFFAOYSA-N

FDA UNII

Y5V2N1KE8U

Antibacterial, potentially toxic, used to treat certain skin diseases.

1 2D Structure

Sulfapyridine

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 MeSH Synonyms

1. Sulphapyridin

2. Sulphapyridine

2.3.2 Depositor-Supplied Synonyms

1. 144-83-2

2. Sulphapyridine

3. 2-sulfapyridine

4. Sulfidin

5. Sulfidine

6. 2-sulfanilamidopyridine

7. 2-sulfanilylaminopyridine

8. Streptosilpyridine

9. Coccoclase

10. Eubasinum

11. Piridazol

12. Pyridazol

13. Eubasin

14. Haptocil

15. Plurazol

16. Relbapiridina

17. Pyriamid

18. Septipulmon

19. Thioseptal

20. Adiplon

21. Dagenan

22. Trianon

23. Ronin

24. 2-sulfanilamidopyridin

25. N-2-pyridylsulfanilamide

26. Solfapiridina

27. Sulfapiridina

28. Sulfapyridinum

29. 4-amino-n-pyridin-2-ylbenzenesulfonamide

30. N1-2-pyridylsulfanilamide

31. N(sup 1)-2-pyridylsulfanilamide

32. 2-(4-aminobenzenesulfonamido)pyridine

33. 2-(p-aminobenzenesulphonamido)pyridine

34. 4-amino-n-pyridin-2-yl-benzenesulfonamide

35. 4-amino-n-(pyridin-2-yl)benzenesulfonamide

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

37. 4-(2-pyridinylsulfonyl)aniline

38. 4-[(2-pyridylamino)sulfonyl]aniline

39. N(sup1)-pyridylsulfanilamide

40. M+b 693

41. N(1)-pyridylsulfanilamide

42. N(1)-2-pyridylsulfanilamide

43. A-499

44. Sulfanilamide, N1-2-pyridyl-

45. 4-amino-n,2-pyridinylbenzenesulfonamide

46. 4-amino-n-(pyridin-2-yl)benzene-1-sulfonamide

47. M + B 693

48. Nsc 4753

49. Nsc 41791

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

51. 4-amino-n-(2-pyridinyl)benzenesulfonamide

52. Chebi:132842

53. Nsc-4753

54. 4-amino-n-2-pyridinylbenzenesulfonamide

55. Nsc-41791

56. Y5v2n1ke8u

57. Mls000069725

58. Nsc4753

59. 2-sulfanilyl Aminopyridine

60. Ncgc00016408-01

61. Cas-144-83-2

62. Smr000058213

63. Solfapiridina [dcit]

64. Dsstox_cid_6067

65. Dsstox_rid_78003

66. Dsstox_gsid_26067

67. Wln: T6nj Bmswr Dz

68. 4-amino-n-(2-pyridyl)benzenesulfonamide

69. Sulfapyridinum [inn-latin]

70. Sulfapiridina [inn-spanish]

71. 2-sulfanilamidopyridin [german]

72. M And B 693

73. Sulfapyridine (tn)

74. M&b 693

75. 4-amino-n-2-pyridinyl-benzenesulfonamide

76. Sr-01000000207

77. N'-2-pyridylsulfanilide

78. Einecs 205-642-7

79. Sulfapyridine (usp/inn)

80. Unii-y5v2n1ke8u

81. Ai3-01049

82. Sulfapyridine [usp:inn:ban]

83. Sulfapyridine Iii

84. Sfy

85. Albb-006215

86. Prestwick_1015

87. Sulfapyridine-13c6

88. Spectrum_000996

89. Sulfapyridine (dagenan)

90. Prestwick0_000762

91. Prestwick1_000762

92. Prestwick2_000762

93. Prestwick3_000762

94. Spectrum2_001323

95. Spectrum3_001773

96. Spectrum4_000346

97. Spectrum5_001182

98. Sulfapyridine [mi]

99. Chembl700

100. Epitope Id:122235

101. Ec 205-642-7

102. Sulfapyridine [inn]

103. Cid_5336

104. Sulfapyridine, >=99.0%

105. Oprea1_344996

106. Schembl44219

107. Bspbio_000804

108. Bspbio_003265

109. Kbiogr_000751

110. Kbioss_001476

111. Ao-801/41077453

112. Divk1c_000216

113. Spectrum1500551

114. Sulfapyridine [mart.]

115. Spbio_001445

116. Spbio_002743

117. Sulfapyridine [usp-rs]

118. Sulfapyridine [who-dd]

119. Bpbio1_000886

120. Zinc2105

121. Dtxsid3026067

122. Bdbm39340

123. Gechumimrbomgk-uhfffaoysa-

124. Hms500k18

125. Kbio1_000216

126. Kbio2_001476

127. Kbio2_004044

128. Kbio2_006612

129. Kbio3_002766

130. Ninds_000216

131. 4-(2-pyridinylsulfonyl)aniline #

132. Hms1570i06

133. Hms1921c03

134. Hms2092k05

135. Hms2097i06

136. Hms2233h20

137. Hms3372n13

138. Hms3714i06

139. Pharmakon1600-01500551

140. Sulfapyridine [orange Book]

141. Hy-b0212

142. Nsc41791

143. Sulfapyridine [usp Impurity]

144. Tox21_110426

145. Ccg-39261

146. Mfcd00038036

147. Nsc757329

148. S1617

149. Stk292439

150. Sulfapyridine [usp Monograph]

151. 2-(p-aminobenzenesulfonamido)pyridine

152. Akos000121424

153. Tox21_110426_1

154. Cs-2157

155. Db00891

156. Hs-0063

157. M&b-693

158. Nsc-757329

159. Idi1_000216

160. Upcmld0enat5889155:001

161. Ncgc00016408-02

162. Ncgc00016408-03

163. Ncgc00016408-04

164. Ncgc00016408-05

165. Ncgc00016408-06

166. Ncgc00016408-09

167. Ncgc00016408-10

168. Ncgc00022008-03

169. Ncgc00022008-04

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

171. Sulfapyridine 100 Microg/ml In Methanol

172. Ac-26818

173. Sbi-0051525.p003

174. Sulfapyridine Melting Point Standard

175. 4-azanyl-n-pyridin-2-yl-benzenesulfonamide

176. Db-042750

177. A 499

178. Ab00052100

179. Bb 0258406

180. Ft-0631839

181. Ft-0674744

182. Sulfasalazine Impurity J [ep Impurity]

183. D02434

184. Ab00052100_14

185. Ab00052100_15

186. A808279

187. Sulfapyridine, Vetranal(tm), Analytical Standard

188. Q3976827

189. Sr-01000000207-2

190. Sr-01000000207-3

191. W-108148

192. Brd-k41406082-001-05-5

193. Brd-k41406082-001-09-7

194. Z271004858

195. 4-amino-n-(1,2-dihydropyridin-2-ylidene)benzenesulfonamide

196. Sulfapyridine, European Pharmacopoeia (ep) Reference Standard

197. 4-amino-n-(pyrimidin-2-yl) Benzenesulfonamide (sulfadiazine) (14)

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

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

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

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₁N₃O₂S
Molecular Weight	249.29 g/mol
XLogP3	0
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	249.05719778 g/mol
Monoisotopic Mass	249.05719778 g/mol
Topological Polar Surface Area	93.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	331
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

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.

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. (See all compounds classified as Anti-Infective Agents.)

Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)

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

Hepatic.

Sulfapyridine has known human metabolites that include Sulfapyridine, N-acetyl.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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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