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Chemistry

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Also known as: Sulfadimidine, 57-68-1, Sulfadimerazine, Sulfamezathine, Sulphamethazine, Sulfadimethyldiazine
Molecular Formula
C12H14N4O2S
Molecular Weight
278.33  g/mol
InChI Key
ASWVTGNCAZCNNR-UHFFFAOYSA-N
FDA UNII
48U51W007F

Sulfadimidine
A sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides.
1 2D Structure

Sulfadimidine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide
2.1.2 InChI
InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
2.1.3 InChI Key
ASWVTGNCAZCNNR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=NC(=N1)NS(=O)(=O)C2=CC=C(C=C2)N)C
2.2 Other Identifiers
2.2.1 UNII
48U51W007F
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Benzenesulfonamide, 4-amino-n-(4,6-dimethyl-2-pyrimidinyl)-

2. Sulfadimezine

3. Sulfadimidine

4. Sulphamethazine

5. Sulphamezathine

2.3.2 Depositor-Supplied Synonyms

1. Sulfadimidine

2. 57-68-1

3. Sulfadimerazine

4. Sulfamezathine

5. Sulphamethazine

6. Sulfadimethyldiazine

7. Sulfadimethylpyrimidine

8. 4-amino-n-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide

9. Sulphamezathine

10. Sulfadimezine

11. Sulfadimidin

12. Sulphadimidine

13. Sulphadimethylpyrimidine

14. Sulfadimesin

15. Sulfadimesine

16. Sulfadimezin

17. Sulfadimidinum

18. Sulfametazyny

19. Sulfamethiazine

20. Sulphamethasine

21. Sulphamidine

22. Sulphodimezine

23. Sulfadine

24. Cremomethazine

25. Sulfadimidina

26. Sulfametazina

27. Sulfodimezine

28. Azolmetazin

29. Dimezathine

30. Intradine

31. Kelametazine

32. Pirmazin

33. Spanbolet

34. Sulfodimesin

35. Superseptil

36. Superseptyl

37. Vertolan

38. Diazil

39. Mermeth

40. Neasina

41. Neazina

42. Sulfa-isodimerazine

43. Dimidin-r

44. Hava-span

45. 4,6-dimethyl-2-sulfanilamidopyrimidine

46. Calfspan Tablets

47. Sa Iii

48. 4-amino-n-(4,6-dimethyl-2-pyrimidinyl)benzenesulfonamide

49. Sulfamidine

50. 2-sulfanilamido-4,6-dimethylpyrimidine

51. Sulfasure Sr Bolus

52. N-(4,6-dimethyl-2-pyrimidyl)sulfanilamide

53. Benzenesulfonamide, 4-amino-n-(4,6-dimethyl-2-pyrimidinyl)-

54. Diazil (the Sulfanilamide)

55. Primazin

56. 2-(p-aminobenzenesulfonamido)-4,6-dimethylpyrimidine

57. 4-amino-n-(2,6-dimethyl-4-pyrimidinyl)benzenesulfonamide

58. A-502

59. 6-(4'-aminobenzol-sulfonamido)-2,4-dimethylpyrimidin

60. N(1)-(4,6-dimethyl-2-pyrimidyl)sulfanilamide

61. Nci-c56600

62. N(1)-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide

63. Sulmet

64. Sulfadimidine;sulfadimerazine

65. (p-aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin

66. Sulfadimidine (inn)

67. Sulfamethazine (usp)

68. Sulfamethazine [usp]

69. 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidine

70. N(sup 1)-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide

71. Chebi:102265

72. Sulfadimezinum

73. Nsc-67457

74. Nsc-683529

75. Sulfanilamide, N(sup1)-(4,6-dimethyl-2-pyrimidinyl)-

76. Mls000069711

77. 4-amino-n-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide

78. Solfadimidina

79. N(sup1)-(2,6-dimethylpyrimid-4-yl)sulfanilamide

80. N(sup1)-(4,6-dimethyl-2-pyrimidyl)sulfanilamide

81. Nsc67457

82. Sulfadimidine-d4

83. Sulfanilamide, N1-(4,6-dimethyl-2-pyrimidinyl)-

84. Sulka S Boluses

85. N(sup1)-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide

86. Nsc683529

87. 48u51w007f

88. 4,6-dimethylsulfadiazine

89. Bn-2409

90. Ncgc00018243-07

91. Smr000017409

92. Solfadimidina [dcit]

93. Sulfametazyny [polish]

94. Dsstox_cid_1290

95. Sulfamethazine 100 Microg/ml In Acetonitrile

96. Sulfadimidine [inn]

97. Dsstox_rid_76062

98. Dsstox_gsid_21290

99. Smz

100. Sulfadimidinum [inn-latin]

101. Sulfadimidina [inn-spanish]

102. Sulfametazina [italian]

103. Sulfadimidine [inn:ban]

104. Cas-57-68-1

105. Bn 2409

106. Ccris 3701

107. Sulfamezathine (tn)

108. Hsdb 4157

109. Einecs 200-346-4

110. Mfcd00006066

111. Nsc 67457

112. Brn 0261304

113. N(sup 1)-(4,6-dimethyl-2-pyrimidyl)sulfanilamide

114. Sulfamethazone

115. Diazilsulfadine

116. Calfspan

117. Panazin

118. Ai3-26817

119. Sulka K Boluses

120. S-dimidine

121. Dimidim-r

122. Unii-48u51w007f

123. 4-amino-n-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide

124. (p-aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin [german]

125. 6-(4'-aminobenzol-sulfonamido)-2,4-dimethylpyrimidin [german]

126. Sulfadimidine,(s)

127. Sulfanilamide, N(1)-(4,6-dimethyl-2-pyrimidinyl)-

128. Sulfadimidine-13c6

129. 4-amino-n-(4,6-dimethyl-2-pyrimidyl)benzenesulfonamide

130. Sulfanilamide, N(sup1)-(2,6-dimethyl-4-pyrimidinyl)-

131. Sentry Aq Mardel Biospheres Maracyn Plus

132. Spectrum_000990

133. [(4-aminophenyl)sulfonyl](4,6-dimethylpyrimidin-2-yl)amine

134. 4-amino-n-(4

135. Opera_id_1374

136. Prestwick0_000775

137. Prestwick1_000775

138. Prestwick2_000775

139. Prestwick3_000775

140. Spectrum2_001321

141. Spectrum3_001700

142. Spectrum4_000344

143. Spectrum5_001270

144. Sulfamethazine, >=99%

145. Chembl446

146. Epitope Id:122238

147. Cambridge Id 5251384

148. Nciopen2_003489

149. Bidd:pxr0093

150. Oprea1_142608

151. Oprea1_677935

152. Bspbio_000850

153. Bspbio_003260

154. Cbdive_012932

155. Kbiogr_000747

156. Kbioss_001470

157. Sulfamethazine [hsdb]

158. Sulfamethazine [iarc]

159. 5-25-10-00250 (beilstein Handbook Reference)

160. Mls000103403

161. Mls001077331

162. Mls002454449

163. Divk1c_000293

164. Schembl151305

165. Spectrum1500548

166. Sulfadimidine [mart.]

167. Sulfamethazine [vandf]

168. Spbio_001441

169. Spbio_002789

170. Sulfadimidine [who-dd]

171. Sulfadimidine [who-ip]

172. Bpbio1_000936

173. Sulfamethazine [usp-rs]

174. Dtxsid6021290

175. Sulfanilamide, N(sup 1)-(4,6-dimethyl-2-pyrimidinyl)-

176. Aswvtgncazcnnr-uhfffaoysa-

177. Hms500o15

178. Kbio1_000293

179. Kbio2_001470

180. Kbio2_004038

181. Kbio2_006606

182. Kbio3_002480

183. Zinc57494

184. Ninds_000293

185. Hms1921a17

186. Hms2092i19

187. Hms3652k03

188. Pharmakon1600-01500548

189. Sulfadimidine [ep Impurity]

190. Sulfamethazine [green Book]

191. Albb-033473

192. Bcp28439

193. Hy-b0035

194. Sulfadimidine [ep Monograph]

195. Sulfadimidine For Peak Identification

196. Sulfamethazine [orange Book]

197. Tox21_110847

198. Tox21_202221

199. Tox21_303006

200. Ccg-39259

201. Nsc757326

202. S3133

203. Stk097514

204. Sulfadimidinum [who-ip Latin]

205. Sulfamethazine [usp Monograph]

206. Akos000119894

207. Sulfose Component Sulfamethazine

208. Tox21_110847_1

209. Db01582

210. Ms-1576

211. Nsc-757326

212. Idi1_000293

213. Terfonyl Component Sulfamethazine

214. Lantrisul Component Sulfamethazine

215. Ncgc00018243-01

216. Ncgc00018243-02

217. Ncgc00018243-03

218. Ncgc00018243-04

219. Ncgc00018243-05

220. Ncgc00018243-06

221. Ncgc00018243-08

222. Ncgc00018243-09

223. Ncgc00021490-03

224. Ncgc00021490-04

225. Ncgc00021490-05

226. Ncgc00021490-06

227. Ncgc00256371-01

228. Ncgc00259770-01

229. Sulfadimidine Solution, 1 Mg/ml In H2o

230. Sulfaloid Component Sulfamethazine

231. Wln: T6n Cnj Bmswr Dz& D1 F1

232. Ac-16126

233. Neotrizine Component Sulfamethazine

234. Sulfamethazine 100 Microg/ml In Methanol

235. Sulfamethazine Component Of Sulfose

236. Sulfanilamide,6-dimethyl-4-pyrimidinyl)-

237. Sbi-0051522.p003

238. Sulfamethazine (trisulfapyrimidines)

239. Sulfamethazine Component Of Terfonyl

240. Trisulfapyrimidines (sulfamethazine)

241. Sulfamethazine 1000 Microg/ml In Methanol

242. Sulfamethazine Component Of Lantrisul

243. Sulfamethazine Component Of Sulfaloid

244. Ft-0655603

245. Ft-0674743

246. N1-(4,6-dimethyl-2-pyrimidyl)sulfanilamide

247. Sulfamethazine Component Of Neotrizine

248. Sw219689-1

249. Benzenesulfonamide,6-dimethyl-4-pyrimidinyl)-

250. Triple Sulfoid Component Sulfamethazine

251. C19530

252. D02436

253. N1-(4,6-dimethyl-2-pyrimidinyl)sulfanilamide

254. Sulfamethazine 1000 Microg/ml In Acetonitrile

255. Ab00052097_12

256. Ab00052097_13

257. Sulfamethazine Component Of Triple Sulfoid

258. A831551

259. Sr-01000000211

260. Sulfamethazine, Vetec(tm) Reagent Grade, >=99%

261. Sulfamethazine, Vetranal(tm), Analytical Standard

262. Q3976823

263. Sr-01000000211-3

264. W-105450

265. 4-amino-n-(4,6-dimethyl-2-pyridyl)benzenesulfonamide

266. Brd-k11640013-001-02-6

267. Brd-k11640013-236-03-6

268. 2-(4-aminobenzenesulfonylamino)-4,6-dimethylpyrimidine

269. F1443-4796

270. Trisulfapyrimidines (sulfamethazine) [orange Book]

271. Sulfadimidine, European Pharmacopoeia (ep) Reference Standard

272. (4-amino-n-(4,6-dimethyl-2-pyrimidinyl)benzene Sulfonamide

273. 4-amino-n~1~-(4,6-dimethyl-2-pyrimidinyl)-1-benzenesulfonamide

274. Hsdb 4157; Hsdb 4157; Hsdb 4157;sulfadimidine;sulfadimerazine

275. Sulfamethazine, United States Pharmacopeia (usp) Reference Standard

276. Sulfadimidine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 278.33 g/mol
Molecular Formula C12H14N4O2S
XLogP30.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass278.08374688 g/mol
Monoisotopic Mass278.08374688 g/mol
Topological Polar Surface Area106 Ų
Heavy Atom Count19
Formal Charge0
Complexity377
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 Therapeutic Uses

Anti-Infective agents

National Library of Medicine's Medical Subject Headings. Sulfamethazine. Online file (MeSH, 2016). Available from, as of January 20, 2016: https://www.nlm.nih.gov/mesh/2016/mesh_browser/MBrowser.html


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Sulfamethazine is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of March 23, 2016: https://clinicaltrials.gov/search/intervention=sulfamethazine


MEDICATION (VET): Sulfamethazine is used as a broad-spectrum antimicrobial to treat or prevent infections caused by susceptible organisms. Infections treated may include pneumonia, intestinal infections (especially coccidia), soft tissue infections and urinary tract infections (UTIs).

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 723


MEDICATION (VET): Sulfadimidine, which is also known as sulfamethazine, is widely used in veterinary medicine in combination with chlortetracycline and penicillin in pigs for maintenance of weight gain in the presence of atrophic rhinitis, growth promotion and increased feed efficiency. Sulfadimidine is also effective against a wide variety of diseases in food-producing animals. Common therapeutic uses in cattle include: treatment of bovine respiratory disease complex (shipping fever complex); necrotic pododermatitis (foot rot) and calf diphtheria; colibacillosis (bacterial scours); coccidiosis and acute mastitis and acute metritis. Common therapeutic uses in sheep include: treatment of pasteurellosis; bacteria pneumonia; colibacillosis (bacterial scours) and control and treatment of coccidiosis. Common therapeutic uses in pigs include: treatment of bacterial pneumonia; porcine colibacillosis (bacterial scours); bacterial swine enteritis; and reduction in the incidence of cervical abscesses. Common therapeutic uses in chickens include: control of infectious coryza; coccidiosis; acute fowl cholera; and pullorum disease. Common therapeutic uses in turkeys include: control of coccidiosis.

WHO/FAO; Thirty-fourth Meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA); Toxicological Evaluation of Certain Veterinary Drug Residues in Food, WHO Food Additive Series 25: Sulfadimidine (1990). Available from, as of April 5, 2016: https://www.inchem.org/pages/jecfa.html


For more Therapeutic Uses (Complete) data for SULFAMETHAZINE (7 total), please visit the HSDB record page.


4.2 Drug Warning

VET: Adverse effects associated with sulfonamides include allergic reactions, Type II and Type III hypersensitivity, arthropathy, anemia, thrombocytopenia, hepatopathy, hypothyroidism (with prolonged therapy), keratoconjunctivitis sicca, and skin reactions. Dogs may be more sensitive to sulfonamides than other animals because dogs lack the ability to acetylate sulfonamides to metabolites. Other, more toxic metabolites may persist. /Sulfonamides/

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 723


VET: Do not administer to animals with sensitivity to sulfonamides. Doberman pinschers may be more sensitive than other canine breeds to reactions from sulfonamides. Use cautiously in this breed. /Sulfonamides/

Papich, M.G. Saunders Handbook of Veterinary Drugs Small and Large Animal. 3rd ed. St. Louis, MO: Elsevier Saunders, 2011, p. 723


4.3 Drug Indication

For the treatment bacterial infections causing bronchitis, prostatitis and urinary tract infections.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Sulfamethazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamethazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.


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.)


5.3 ATC Code

J01EB03

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


J01EB03

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


J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01E - Sulfonamides and trimethoprim

J01EB - Short-acting sulfonamides

J01EB03 - Sulfadimidine


5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following oral administration.


The pharmacokinetics and metabolism of sulfadimidine (SDM) following intravenous administration of 100 mg/kg were studied in seven dwarf preruminant kids at 12 weeks of age, and again at the ruminant stage, when the animals were 18 weeks old. The persistence of SDM in 18-week-old kids was prolonged in comparison to the 12-week-old animals: a lower total body clearance and a prolonged elimination of SDM were obtained in the older animals. The renal clearance values of SDM and its metabolites were the same at both ages. The decrease of SDM clearance is related to the significant reduction in SDM hydroxylation at the older age. The reduced oxidative hepatic metabolism may result from the sexual maturation of the kids.

PMID:2704056 Nouws JF et al; J Vet Pharmacol Ther. 1989 Mar;12(1):19-24


Sulfamethazine acetylation phenotypes were determined in 19 healthy adults (aged 17-46 years; 15 men, four women; nine white, nine oriental, one black) given a single oral dose of 20 mg/kg bw sulfamethazine in 200 mL of water. The results showed a welldefined trimodal pattern for acetylation clearance and for overall elimination or metabolic rate constants and confirmed that the fast acetylator phenotype can be subdivided into intermediate and rapid acetylator groups. The average acetylation clearance rate for rapid acetylators (1.34 mL/min per kg bw) was 8.8 times the estimated clearance for slow acetylators (0.15 mL/min per kg bw) and 1.8 times that for intermediate acetylators (0.75 mL/min per kg bw). The average percentage of an absorbed dose excreted as acetylsulfamethazine in 72-hr urine was 93.7 for rapid acetylators, 87.7 for intermediate acetylators and 65.6 for slow acetylators.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V79 346-7 (2001)


The depletion of sulfadimidine (SDM) and its N4-acetyl and hydroxy metabolites was studied in eggs laid by hens after administration of either a single or multiple oral dosages of 100 mg SDM/kg. During medication and until 1 day after the last dose, the SDM and its metabolite concentrations in the egg white exceeded those in the egg yolk and reflected the plasma levels. In the period starting 2 days after the (last) dosage, the SDM concentration in the yolk became higher than in the egg white, and the drug depletion curves ran parallel. The mean maximum amount of SDM found in the whole egg was 1500 micrograms after a single and 1280 ug after multiple dosage. In eggs, traces of the N4-acetyl and 6-methylhydroxy metabolites could be detected (mainly in the egg white), and their concentrations were approximately 40 times lower than those of the parent drug. A highly significant correlation (P less than 0.005) was found between the development stage of the oocyte at the time of (last) medication and the amount of SDM found in the egg that developed from it. A period of 7 or 8 days after the (last) dosage of 100 mg SDM/kg/day is required to obtain SDM levels below 0.1 ug/g egg.

PMID:3564319 Geertsma MF et al; Vet Q 9 (1): 67-75 (1987)


Relatively strong blood-brain barrier to sulfamethazine was observed in rats. Passage of sulfamethazine from blood to brain was slow and difficult.

Siddique et al; Acta Vet Brno 48 (1-2-3-4): 79 (1980)


For more Absorption, Distribution and Excretion (Complete) data for SULFAMETHAZINE (12 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

Plasma disposition of sulfadimidine (SDM) and its metabolites was studied in laying hens after 100 mg SDM kg-1 doses were administered as a single intravenous dose, a single oral dose and multiple oral doses once daily for five consecutive days. SDM was extensively metabolized by acetylation and hydroxylation. In plasma, the metabolite observed with the highest concentration was N4-acetylsulfadimidine (N4-SDM) followed by hydroxymethylsulfadimidine (CH2OH) and 5-hydroxysulfadimidine. Following intravenous administration a biphasic elimination (as seen for a capacity limited reaction) pattern for SDM and its metabolites was observed. Multiple (5x) SDM dosing revealed plasma SDM concentrations ranging between 7 and 108 ug mL-1; within 96 hours of termination of the multiple SDM dosing, the plasma SDM concentration was below 0.01 ug mL-1. The renal clearances of N4-SDM and the hydroxy metabolites were approximately 10 times greater than that of SDM. The SDM mass balance (fecal/urinary recovery) showed a loss of 56 per cent after intravenous dosage and of 67 per cent after a single oral dosage; the hydroxy metabolites accounted for the highest percentage in feces/urine. Thus additional metabolic pathways must exist in laying hens.

PMID:3387673 Nouws JF et al; Res Vet Sci 44 (2): 202-7 (1988)


After 10 male and two female healthy volunteers were given oral doses of sulfamethazine of 12-17 mg/kg bw, 10-20% of the dose was excreted in the urine as free and conjugated hydroxylated metabolites and 61-81% as N4-acetylsulfamethazine. Six of the individuals were considered to be fast acetylators and six slow acetylators. The plasma concentration-time curve for sulfamethazine in the fast acetylators was biphasic, with half-times of 1.7 and 5.4 hr, respectively, whereas in the slow acetylators it was monophasic, with a half-time of 7.6 hr.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V79 347 (2001)


Sulfamethazine is metabolized similarly in animals and humans, with N4-acetylation dominating. A trimodal pattern of sulfamethazine acetylation is seen in humans. Differences in acetylation rates were observed between male and female rats and among females of different strains.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V79 348 (2001)


The pharmacokinetics of sulfamethizole, sulfamethoxazole, sulfadiazine, sulfapyridine and sulfadimidine have been studied in man. Renal clearance values of the metabolite N4-acetylsulphonamide are 6 to 20 times higher than those of the corresponding parent compound. The renal clearance of sulfonamides is dependent on the urine flow. N4-Acetylsulfonamide concentration-time profiles for plasma and urine have been constructed for the sulfonamides. The percentage N4-acetylsulfonamide-time profiles for plasma are excellent tools for establishing the acetylator phenotype, while those constructed from urine samples are less useful. Evidence is obtained that sulfadimidine is metabolically processes by 2 different isoenzymes, while sulfadiazine, sulfapyridine and sulfamethoxazole are processes by 1 acetylating isoenzyme. Sulfamethizole is acetylated to very little extent.

PMID:7389236 Vree TB et al; Clin Pharmacokinet 5 (3) :274-94 (1980)


For more Metabolism/Metabolites (Complete) data for SULFAMETHAZINE (9 total), please visit the HSDB record page.


5.6 Biological Half-Life

After 10 male and two female healthy volunteers were given oral doses of sulfamethazine of 12-17 mg/kg bw, 10-20% of the dose was excreted in the urine as free and conjugated hydroxylated metabolites and 61-81% as N4-acetylsulfamethazine. Six of the individuals were considered to be fast acetylators and six slow acetylators. The plasma concentration-time curve for sulfamethazine in the fast acetylators was biphasic, with half-times of 1.7 and 5.4 hr, respectively, whereas in the slow acetylators it was monophasic, with a half-time of 7.6 hr.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V79 347 (2001)


Sulfadimidine is acetylated and hydroxylated in humans. ... The plasma concentration-time curve of sulfadimidine in fast acetylators is biphasic, with half-lives of 1.7 and 5.4 hr, whereas that in slow acetylators is monophasic, with a half-life of 7.6 hr. ...

PMID:3824429 Vree TB et al; Ther Drug Monit 8 (4): 434-9 (1986)


... /Following oral administration to swine,/ the mean half-life for sulfamethazine, the N4-glucose conjugate of sulfamethazine, and N4-acetylsulfamethazine was estimated to be 0.8 day. ...

PMID:2870889 Mitchell AD, Paulson GD; Drug Metab Dispos 14 (2): 161-5 (1986)


5.7 Mechanism of Action

Sulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.


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06-Feb-2021
28-Aug-2024
KGS
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