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Chemistry

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Also known as: 68-35-9, Sulphadiazine, Sulfapyrimidine, Sulfadiazin, Adiazine, Sulfazine

Molecular Formula

C₁₀H₁₀N₄O₂S

Molecular Weight

250.28 g/mol

InChI Key

SEEPANYCNGTZFQ-UHFFFAOYSA-N

FDA UNII

0N7609K889

One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.

Sulfadiazine is a Sulfonamide Antibacterial.

1 2D Structure

Sulfadiazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-N-pyrimidin-2-ylbenzenesulfonamide

2.1.2 InChI

InChI=1S/C10H10N4O2S/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10/h1-7H,11H2,(H,12,13,14)

2.1.3 InChI Key

SEEPANYCNGTZFQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CN=C(N=C1)NS(=O)(=O)C2=CC=C(C=C2)N

2.2 Other Identifiers

2.2.1 UNII

0N7609K889

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Sulfadiazine, Zinc

2. Sulfazin

3. Sulfazine

4. Sulphadiazine

5. Zinc Sulfadiazine

2.3.2 Depositor-Supplied Synonyms

1. 68-35-9

2. Sulphadiazine

3. Sulfapyrimidine

4. Sulfadiazin

5. Adiazine

6. Sulfazine

7. Sulfadiazene

8. Adiazin

9. Debenal

10. Pyrimal

11. Liquadiazine

12. Sulfapyrimidin

13. 2-sulfanilamidopyrimidine

14. Coco-diazine

15. Cremodiazine

16. Spofadrizine

17. Theradiazine

18. Cremotres

19. Deltazina

20. Diazolone

21. Eskadiazine

22. Microsulfon

23. Neotrizine

24. Palatrize

25. Piridisir

26. Quadetts

27. Quadramoid

28. Sanodiazine

29. Sterazine

30. Sulfatryl

31. Sulfolex

32. Sulfonsol

33. Terfonyl

34. Trifonamide

35. Truozine

36. Diazin

37. Neazine

38. Pirimal

39. Sulfose

40. Trisem

41. Sulfanilamidopyrimidine

42. Honey Diazine

43. Lipo-levazine

44. Tri-sulfameth

45. Triple Sulfas

46. Lipo-diazine

47. Metha-meridiazine

48. Sulfadiazinum

49. Diazovit

50. Sulfadiazina

51. Sulphadiazine E

52. 4-amino-n-(pyrimidin-2-yl)benzenesulfonamide

53. Sulfapirimidin

54. Di-azo-mul

55. Thi-di-mer

56. 2-sulfanilylaminopyrimidine

57. Benzenesulfonamide, 4-amino-n-2-pyrimidinyl-

58. Codiazine

59. Silvadene

60. Pecta-diazine, Suspension

61. 4-amino-n-pyrimidin-2-ylbenzenesulfonamide

62. Rp 2616

63. Pyrimidine, 2-sulfanilamido-

64. 2-sulfapyrimidine

65. N(1)-2-pyrimidylsulfanilamide

66. N(1)-2-pyrimidinylsulfanilamide

67. 4-amino-n-2-pyrimidinylbenzenesulfonamide

68. N(sup 1)-2-pyrimidinylsulfanilamide

69. 4-amino-n-(pyrimidin-2-yl)benzene-1-sulfonamide

70. Sulfanilamide, N1-2-pyrimidinyl-

71. 4-amino-n-pyrimidin-2-yl-benzenesulfonamide

72. Chebi:9328

73. Sulfanilamide, N(sup 1)-2-pyrimidinyl-

74. 4-amino-n-2-pyrimidinyl-benzenesulfonamide

75. N(sup1)-2-pyrimidylsulfanilamide

76. Sulfanilamide, N1-2(1h)-pyrimidinylidene-

77. Silver Sulfadiazine

78. A-306

79. N(sup1)-2-pyrimidinylsulfanilamide

80. Chembl439

81. S. N. 112

82. Nsc35600

83. Nsc-35600

84. Cas-68-35-9

85. Ncgc00016305-01

86. Solfadiazina

87. Cocodiazine

88. Solfadiazina [dcit]

89. Sulfadiazine 100 Microg/ml In Acetonitrile

90. 0n7609k889

91. 2-sulfanilamidopyrimidin

92. Nsc117870

93. Sulfapyrimidin [german]

94. Sdz

95. Sulfadiazinum [inn-latin]

96. Sulfadiazina [inn-spanish]

97. Sildaflo

98. S.n. 112

99. 2-sulfanilamidopyrimidin [german]

100. A-306 (van)

101. 4-amino-n-(2-pyrimidinyl)benzenesulfonamide

102. A 306

103. Smr000059113

104. Sulfadiazine (tn)

105. N-(2-pyrimidinyl)sulfanilamide

106. Rbpi21 & Sulfa

107. Rp-2616

108. Sr-01000002973

109. Ssd

110. Einecs 200-685-8

111. Mfcd00006065

112. Nsc 35600

113. 2-sulfanilamido-pyrimidine

114. Brn 0235192

115. Diazine

116. Crl-8131 & Sulfadiazine

117. N1-2-pyrimidinylsulfanilamide

118. Sulfadiazine (jan/usp/inn)

119. Ai3-01047

120. Sulfadiazine,(s)

121. Trisulfapyrimidine, Oral Suspension

122. Unii-0n7609k889

123. Sulfadiazine [usp:inn:ban:jan]

124. Prestwick_428

125. Spectrum_000986

126. Sulfadiazina Reig Jofre

127. Sulfacombin (salt/mix)

128. Prestwick0_000023

129. Prestwick1_000023

130. Prestwick2_000023

131. Prestwick3_000023

132. Spectrum2_001319

133. Spectrum3_001362

134. Spectrum4_000342

135. Spectrum5_000992

136. Sulfadiazine [mi]

137. [(4-aminophenyl)sulfonyl]pyrimidin-2-ylamine

138. Sulfadiazine [inn]

139. Sulfadiazine [jan]

140. Epitope Id:140083

141. N1-2-pyrimidylsulfanilamide

142. Sulfadiazine, >=99.0%

143. Dsstox_cid_24130

144. Dsstox_rid_80105

145. Sulfadiazine [vandf]

146. Dsstox_gsid_44130

147. Oprea1_081078

148. Schembl24176

149. Bspbio_000085

150. Bspbio_002884

151. Kbiogr_000743

152. Kbioss_001466

153. Sulfadiazine [mart.]

154. 5-25-10-00067 (beilstein Handbook Reference)

155. Mls000069423

156. Mls006011457

157. Divk1c_000543

158. Spectrum1500546

159. Sulfadiazine [usp-rs]

160. Sulfadiazine [who-dd]

161. Spbio_001417

162. Spbio_002006

163. Bpbio1_000095

164. Wln: T6n Cnj Bmswr Dz

165. Dtxsid7044130

166. Hms501l05

167. Kbio1_000543

168. Kbio2_001466

169. Kbio2_004034

170. Kbio2_006602

171. Kbio3_002104

172. Sulfadiazine [green Book]

173. Ninds_000543

174. Glxc-25873

175. Hms1568e07

176. Hms1921a13

177. Hms2090p09

178. Hms2092i15

179. Hms2095e07

180. Hms2235d19

181. Hms3371l19

182. Hms3655i10

183. Hms3712e07

184. Pharmakon1600-01500546

185. Sulfadiazine [orange Book]

186. Zinc120319

187. Sulfadiazine [ep Monograph]

188. Sulfadiazine [usp Impurity]

189. Albb-014888

190. Amy33423

191. Bcp12140

192. Hy-b0273

193. Sulfadiazine [usp Monograph]

194. Tox21_110360

195. Bbl013169

196. Bdbm50166571

197. Ccg-39257

198. Nsc757324

199. Recombinant Bactericidal/permeability-increasing Protein & Sulfadiazine

200. S1770

201. Stk317797

202. Sulfose Component Sulfadiazine

203. Terfonyl Component Sulfadiazine

204. 2-(p-aminobenzenesulfonamido)pyrimidin

205. Akos000119073

206. Lantrisul Component Sulfadiazine

207. Sulfaloid Component Sulfadiazine

208. Db00359

209. Ks-1144

210. Nsc-757324

211. Sulfadiazin 100 Microg/ml In Methanol

212. 2-(4-aminobenzenesulfonamido)pyrimidine

213. 4-amino-n-2-pyrimidylbenzenesulfonamide

214. Idi1_000543

215. Neotrizine Component Sulfadiazine

216. Sulfadiazine Component Of Sulfose

217. Ncgc00016305-02

218. Ncgc00016305-03

219. Ncgc00016305-04

220. Ncgc00016305-05

221. Ncgc00016305-06

222. Ncgc00016305-09

223. Ncgc00016305-10

224. Ncgc00016305-11

225. Ncgc00023291-03

226. Ncgc00023291-04

227. Sulfadiazine (trisulfapyrimidines)

228. Sulfadiazine Component Of Terfonyl

229. Trisulfapyrimidines (sulfadiazine)

230. 2-(4-aminobenzenesulfonylamino)pyrimidine

231. Ac-26817

232. Sulfadiazine 1000 Microg/ml In Methanol

233. Sulfadiazine Component Of Lantrisul

234. Sulfadiazine Component Of Sulfaloid

235. 4-amino-n-2-pyrimidinyl Benzenesulfonamide

236. Mixture Of Sulfadiazine, And Sulfamethazine

237. Sbi-0051520.p003

238. Sulfadiazine Component Of Neotrizine

239. Triple Sulfoid Component Sulfadiazine

240. 4-[[(pyrimidin-2-yl)amino]sulfonyl]aniline

241. Ab00052095

242. Benzenesulfonamide,4-amino-n-2-pyrimidinyl-

243. Ft-0674739

244. Ft-0674740

245. Ft-0674741

246. S0579

247. Sulfadiazine For Identification Of Impurity F

248. Sw196657-3

249. 4-amino-n-(2-pyrimidinyl) Benzenesulfonamide

250. Sulfadimidine Impurity B [ep Impurity]

251. 4-amino-n-(2-pyrimidinyl)benzenesulfonamide #

252. 68s359

253. C07658

254. D00587

255. D92267

256. Sulfadiazine Component Of Triple Sulfoid

257. Trisulfapyrimidine, Oral Suspension (salt/mix)

258. Ab00052095-13

259. Ab00052095-14

260. Ab00052095_15

261. Ab00052095_16

262. Benzenesulfonamide, 4-amino-n-(2-pyrimidinyl)-

263. Sulfadiazine, Vetranal(tm), Analytical Standard

264. Sulfonamides Duplex Component Sulfadiazine

265. A836115

266. Q-201759

267. Q2555060

268. Sr-01000002973-2

269. Sr-01000002973-3

270. Sulfadiazine Component Of Sulfonamides Duplex

271. Brd-k32273377-001-05-4

272. Brd-k32273377-001-09-6

273. F1657-1720

274. Sulfadiazine, Certified Reference Material, Tracecert(r)

275. Trisulfapyrimidines (sulfadiazine) [orange Book]

276. Z271004844

277. Sulfadiazine, European Pharmacopoeia (ep) Reference Standard

278. Sulfadiazine, United States Pharmacopeia (usp) Reference Standard

279. 4-amino-n-(2-pyrimidinyl)benzenesulfonamide, N1-(pyrimidin-2-yl)sulfanilamide

280. Sulfadiazine, Pharmaceutical Secondary Standard; Certified Reference Material

281. 141582-64-1

282. Sulfadiazine For Identification Of Impurity F, European Pharmacopoeia (ep) Reference Standard

2.3.3 Other Synonyms

1. Sulfadiazine Sodium

2. Sodium Sulfadiazine

3. Sodium Sulfapyrimidine

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₀N₄O₂S
Molecular Weight	250.28 g/mol
XLogP3	-0.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	250.05244675 g/mol
Monoisotopic Mass	250.05244675 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	327
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 Information

1 of 8
Drug Name	Silvadene
PubMed Health	Silver Sulfadiazine (On the skin)
Drug Classes	Antibacterial
Active Ingredient	Silver sulfadiazine
Dosage Form	Cream
Route	Topical
Strength	1%
Market Status	Prescription
Company	King Pharms

2 of 8
Drug Name	Ssd
PubMed Health	Sulfadiazine (By mouth)
Drug Classes	Antibiotic
Active Ingredient	Silver sulfadiazine
Dosage Form	Cream
Route	Topical
Strength	1%
Market Status	Prescription
Company	Dr Reddys La

3 of 8
Drug Name	Sulfadiazine
PubMed Health	Silver Sulfadiazine (On the skin)
Drug Classes	Antibacterial
Drug Label	Sulfadiazine is an oral sulfonamide anti-bacterial agent.Each tablet, for oral administration, contains 500 mg sulfadiazine. In addition, each tablet contains the following inactive ingredients: croscarmellose sodium, docusate sodium, microcrystallin...
Active Ingredient	Sulfadiazine
Dosage Form	Tablet
Route	Oral
Strength	500mg
Market Status	Prescription
Company	Sandoz

4 of 8
Drug Name	Thermazene
Active Ingredient	Silver sulfadiazine
Dosage Form	Cream
Route	Topical
Strength	1%
Market Status	Prescription
Company	Thepharmanetwork

5 of 8
Drug Name	Silvadene
PubMed Health	Silver Sulfadiazine (On the skin)
Drug Classes	Antibacterial
Active Ingredient	Silver sulfadiazine
Dosage Form	Cream
Route	Topical
Strength	1%
Market Status	Prescription
Company	King Pharms

6 of 8
Drug Name	Ssd
PubMed Health	Sulfadiazine (By mouth)
Drug Classes	Antibiotic
Active Ingredient	Silver sulfadiazine
Dosage Form	Cream
Route	Topical
Strength	1%
Market Status	Prescription
Company	Dr Reddys La

7 of 8
Drug Name	Sulfadiazine
PubMed Health	Silver Sulfadiazine (On the skin)
Drug Classes	Antibacterial
Drug Label	Sulfadiazine is an oral sulfonamide anti-bacterial agent.Each tablet, for oral administration, contains 500 mg sulfadiazine. In addition, each tablet contains the following inactive ingredients: croscarmellose sodium, docusate sodium, microcrystallin...
Active Ingredient	Sulfadiazine
Dosage Form	Tablet
Route	Oral
Strength	500mg
Market Status	Prescription
Company	Sandoz

8 of 8
Drug Name	Thermazene
Active Ingredient	Silver sulfadiazine
Dosage Form	Cream
Route	Topical
Strength	1%
Market Status	Prescription
Company	Thepharmanetwork

4.2 Drug Indication

For the treatment of rheumatic fever and meningococcal meningitis

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sulfadiazine 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-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Coccidiostats

Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals. (See all compounds classified as Coccidiostats.)

Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

SULFADIAZINE

5.3.2 FDA UNII

0N7609K889

5.3.3 Pharmacological Classes

Sulfonamides [CS]; Sulfonamide Antibacterial [EPC]

5.4 ATC Code

J01EC02

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

J01EC02

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BA - Sulfonamides

D06BA01 - Silver sulfadiazine

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01E - Sulfonamides and trimethoprim

J01EC - Intermediate-acting sulfonamides

J01EC02 - Sulfadiazine

5.5 Absorption, Distribution and Excretion

Route of Elimination

Sulfadiazine is excreted largely in the urine.

5.6 Metabolism/Metabolites

Sulfadiazine has known human metabolites that include Sulfadiazine hydroxylamine.

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

5.7 Mechanism of Action

Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

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API Reference Price

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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ACTIVE PHARMA INGREDIENTS

22 API Suppliers

5 USDMF

5 CEP/COS

1 JDMF

13 NDC API

3 VMF

13 Listed Suppliers

$ API Reference Price

FINISHED DOSAGE FORMULATIONS

24 FDF Dossiers

9 FDA Orange Book

5 Europe

2 Canada

8 Listed Dossiers

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11 BASF

4 DFE Pharma

4 Gangwal Chemicals

1 Ideal Cures Pvt Ltd

2 Ingredion Pharma Solutions

3 Kerry

5 Microlex e.U

1 Novo Excipients

3 Pharmatrans-Sanaq

2 Pluviaendo

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14 Roquette

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10 Sigachi Industries

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EXCIPIENTS BY APPLICATIONS

27 Fillers, Diluents & Binders

25 Disintegrants & Superdisintegrants

21 Direct Compression

14 Granulation

12 Thickeners and Stabilizers

9 Co-Processed Excipients

7 Coating Systems & Additives

7 Solubilizers

7 Controlled & Modified Release

6 Lubricants & Glidants

6 Film Formers & Plasticizers

2 Rheology Modifiers

2 Chewable & Orodispersible Aids

2 Parenteral

2 Taste Masking

1 Topical

GLOBAL SALES INFORMATION

3 US Medicaid Prescriptions

5 Finished Drug Prices

MARKET PLACE

11 APIs

2 FDF Dossiers

REF. STANDARDS & IMPURITIES

4 EDQM

2 USP

1 Others

ACTIVE PHARMA INGREDIENTS

API REF. PRICE (USD/KG)

$ 368

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