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Synopsis

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Chemistry

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Also known as: 127-79-7, Sulphamerazine, Sulfamerazin, Sulfamethyldiazine, Cremomerazine, Methylsulfazine

Molecular Formula

C₁₁H₁₂N₄O₂S

Molecular Weight

264.31 g/mol

InChI Key

QPPBRPIAZZHUNT-UHFFFAOYSA-N

FDA UNII

UR1SAB295F

A sulfanilamide that is used as an antibacterial agent.

1 2D Structure

Sulfamerazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-N-(4-methylpyrimidin-2-yl)benzenesulfonamide

2.1.2 InChI

InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)

2.1.3 InChI Key

QPPBRPIAZZHUNT-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=NC(=NC=C1)NS(=O)(=O)C2=CC=C(C=C2)N

2.2 Other Identifiers

2.2.1 UNII

UR1SAB295F

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Mebacid

2. Methylsulfadiazine

3. Trimetox

2.3.2 Depositor-Supplied Synonyms

1. 127-79-7

2. Sulphamerazine

3. Sulfamerazin

4. Sulfamethyldiazine

5. Cremomerazine

6. Methylsulfazine

7. Sulfameradine

8. Mebacid

9. Mesulfa

10. Metilsulfadiazin

11. 2-sulfa-4-methylpyrimidine

12. 4-amino-n-(4-methylpyrimidin-2-yl)benzenesulfonamide

13. Methylpyrimal

14. Metilsulfazin

15. Sulfamerazina

16. Sulfamerazinum

17. Kelamerazine

18. Percoccide

19. Pyralcid

20. Septacil

21. Septosyl

22. Solumedin

23. Sumedine

24. Romezin

25. Veta-merazine

26. Debenal-m

27. Pirimal-m

28. Pyrimal M

29. Methylsulfazin

30. Benzenesulfonamide, 4-amino-n-(4-methyl-2-pyrimidinyl)-

31. N-(4-methyl-2-pyrimidyl)sulfanilamide

32. 2-(sulfanilamido)-4-methylpyrimidine

33. 2-(4-aminobenzenesulfonamido)-4-methylpyrimidine

34. 4-amino-n-(4-methyl-2-pyrimidinyl)-benzenesulfonamide

35. 2643-rp

36. Rp 2632

37. N1-(4-methyl-2-pyrimidinyl)sulfanilamide

38. (p-aminobenzolsulfonyl)-2-amino-4-methylpyrimidin

39. A-310

40. 4-amino-n-(4-methyl-2-pyrimidinyl)benzenesulfonamide

41. Nsc 27259

42. Rp2632

43. Sulfanilamide, N1-(4-methyl-2-pyrimidinyl)-

44. Solumedine

45. Sulfamerazine (inn)

46. Chebi:102130

47. 2-sulfanilamido-4-methylpyrimidine

48. 2632 R. P.

49. N(1)-(4-methyl-2-pyrimidinyl)sulfanilamide

50. 2-(p-aminobenzolsulfonamido)-4-methylpyrimidine

51. Nsc-27259

52. Ur1sab295f

53. Mls000551747

54. Solfamerazina

55. Sulfanilamide, N(sup 1)-(4-methyl-2-pyrimidinyl)-

56. Ncgc00016386-01

57. Cas-127-79-7

58. Smr000145672

59. Solfamerazina [dcit]

60. Sulfamerazine 100 Microg/ml In Acetonitrile

61. Dsstox_cid_3612

62. Sulfamerazine [inn]

63. Dsstox_rid_77109

64. Dsstox_gsid_23612

65. Sulfamerazinum [inn-latin]

66. Sulfamerazina [inn-spanish]

67. 4-amino-n-(4-methyl-pyrimidin-2-yl)-benzenesulfonamide

68. 4-amino-n-(4-methylpyrimidin-2-yl)

69. Sr-01000684857

70. Einecs 204-866-2

71. N(sup 1)-(4-methyl-2-pyrimidinyl)sulfanilamide

72. Unii-ur1sab295f

73. Brn 0249133

74. 4-amino-n-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide

75. Ai3-08026

76. Sulfamerazine [usp:inn:ban]

77. (p-aminobenzolsulfonyl)-2-amino-4-methylpyrimidin [german]

78. Prestwick_17

79. Mfcd00023212

80. N,n-dialkylarylamine

81. Sulfamerazine-13c6

82. Spectrum_000003

83. N1-(4-methylpyrimidin-2-yl)sulfanilamide

84. Opera_id_988

85. Prestwick0_000694

86. Prestwick1_000694

87. Prestwick2_000694

88. Prestwick3_000694

89. Spectrum2_001320

90. Spectrum3_001363

91. Spectrum4_000343

92. Spectrum5_001413

93. 2(p-aminobenzolsulfonamido)-4-methylpyrimidin

94. Sulfamerazine [mi]

95. Chembl438

96. Epitope Id:122236

97. N(sup1)-(4-methyl-2-pyrimidinyl)sulfanilamide

98. Schembl33999

99. Bspbio_000847

100. Bspbio_002886

101. Kbiogr_000745

102. Kbioss_000343

103. Sulfamerazine [vandf]

104. 5-25-10-00167 (beilstein Handbook Reference)

105. Mls001201765

106. Divk1c_000563

107. Spectrum1500547

108. Sulfamerazine [mart.]

109. Spbio_001419

110. Spbio_002768

111. Sulfamerazine [usp-rs]

112. Sulfamerazine [who-dd]

113. Bpbio1_000933

114. Dtxsid0023612

115. Hms501m05

116. Kbio1_000563

117. Kbio2_000343

118. Kbio2_002911

119. Kbio2_005479

120. Kbio3_002106

121. Zinc57501

122. Ninds_000563

123. Hms1570k09

124. Hms1921a15

125. Hms2092i17

126. Hms2097k09

127. Hms2234d16

128. Hms3374k04

129. Hms3652i03

130. Hms3714k09

131. Pharmakon1600-01500547

132. Sulfamerazine [green Book]

133. Sulfamerazine [orange Book]

134. Albb-025702

135. Amy23374

136. Hy-b0512

137. Nsc27259

138. Sulfamerazine [ep Monograph]

139. Tox21_110411

140. Bbl003544

141. Ccg-39258

142. Nsc757325

143. S3132

144. Stk520614

145. Sulfose Component Sulfamerazine

146. Akos005143010

147. Terfonyl Component Sulfamerazine

148. Tox21_110411_1

149. Db01581

150. Ks-5323

151. Nsc-757325

152. Idi1_000563

153. Lantrisul Component Sulfamerazine

154. Sulfaloid Component Sulfamerazine

155. Ncgc00016386-02

156. Ncgc00016386-03

157. Ncgc00016386-06

158. Ncgc00094787-01

159. Ncgc00094787-02

160. Neotrizine Component Sulfamerazine

161. Sulfamerazine 100 Microg/ml In Methanol

162. Sulfamerazine Component Of Sulfose

163. N'-(4-methyl-2-pyrimidyl) Sulfanilamide

164. Sulfamerazine (trisulfapyrimidines)

165. Sulfamerazine Component Of Terfonyl

166. Trisulfapyrimidines (sulfamerazine)

167. Sbi-0051521.p003

168. Sulfamerazine 1000 Microg/ml In Methanol

169. Sulfamerazine Component Of Lantrisul

170. Sulfamerazine Component Of Sulfaloid

171. Db-041873

172. Sulfamerazine Component Of Neotrizine

173. Sulfamerazine, Reagentplus(r), >=99.0%

174. Ab00052096

175. Ft-0631745

176. Ft-0645132

177. Sw196334-3

178. Triple Sulfoid Component Sulfamerazine

179. Sulfadimidine Impurity A [ep Impurity]

180. Sulfamerazine, Vetec(tm) Reagent Grade, 98%

181. 2-(p-aminobenzosulfonamido)-4-methylpyrimidine

182. D02435

183. D84140

184. Ab00052096-13

185. Ab00052096_15

186. Ab00052096_16

187. Sulfamerazine Component Of Triple Sulfoid

188. A805747

189. Q415196

190. Sulfamerazine, Vetranal(tm), Analytical Standard

191. Sulfonamides Duplex Component Sulfamerazine

192. Q-201761

193. Sr-01000684857-2

194. Sr-01000684857-4

195. Brd-k93524252-001-05-6

196. Brd-k93524252-001-15-5

197. Sulfamerazine Component Of Sulfonamides Duplex

198. F2190-0484

199. N(sup 1)-(4-methyl-2- Pyrimidinyl)sulfanilamide

200. Trisulfapyrimidines (sulfamerazine) [orange Book]

201. Sulfamerazine, European Pharmacopoeia (ep) Reference Standard

202. Sulfamerazine, United States Pharmacopeia (usp) Reference Standard

203. Sulfamerazine, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₂N₄O₂S
Molecular Weight	264.31 g/mol
XLogP3	0.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	264.06809681 g/mol
Monoisotopic Mass	264.06809681 g/mol
Topological Polar Surface Area	106 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	360
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

A sulfanilamide that is used as an antibacterial agent. It can be used to treat bronchitis, prostatitis and urinary tract infections.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthetase (DHPS), an enzyme involved in folate synthesis in bacteria.

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.)

5.3 ATC Code

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06B - Chemotherapeutics for topical use

D06BA - Sulfonamides

D06BA06 - Sulfamerazine

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01E - Sulfonamides and trimethoprim

J01ED - Long-acting sulfonamides

J01ED07 - Sulfamerazine

5.4 Absorption, Distribution and Excretion

Absorption

Rapidly absorbed following oral administration.

5.5 Metabolism/Metabolites

Sulfamerazine has known human metabolites that include N(4)-Acetylsulfamerazine.

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

5.6 Mechanism of Action

Sulfamerazine 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). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.

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