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Chemistry

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Also known as: 2447-57-6, Sulphadoxine, Sulforthomidine, Sulfadoxin, 4-amino-n-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide, Fanasil

Molecular Formula

C₁₂H₁₄N₄O₄S

Molecular Weight

310.33 g/mol

InChI Key

PJSFRIWCGOHTNF-UHFFFAOYSA-N

FDA UNII

88463U4SM5

A long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections.

Sulfadoxine is a Sulfonamide.

1 2D Structure

Sulfadoxine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide

2.1.2 InChI

InChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)

2.1.3 InChI Key

PJSFRIWCGOHTNF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=C(N=CN=C1OC)NS(=O)(=O)C2=CC=C(C=C2)N

2.2 Other Identifiers

2.2.1 UNII

88463U4SM5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fanasil

2. Ro 4 4393

3. Ro 4-4393

4. Ro 44393

5. Sulformethoxine

6. Sulformetoxine

7. Sulforthomidine

8. Sulphormetoxin

9. Sulphorthodimethoxine

2.3.2 Depositor-Supplied Synonyms

1. 2447-57-6

2. Sulphadoxine

3. Sulforthomidine

4. Sulfadoxin

5. 4-amino-n-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide

6. Fanasil

7. Sulphormethoxine

8. Sulfadoxinum

9. Sulfadoxina

10. Fanzil

11. Ro 4-4393

12. 4-amino-n-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide

13. 4-sulfanilamido-5,6-dimethoxypyrimidine

14. Benzenesulfonamide, 4-amino-n-(5,6-dimethoxy-4-pyrimidinyl)-

15. Fanasulf

16. N'-(5,6-dimethoxy-4-pyrimidyl)sulfanilamide

17. 6-(4-aminobenzenesulfonamido)-4,5-dimethoxypyrimidine

18. Sulfadoxine (sulphadoxine)

19. Nsc-759319

20. Ro-4-4393

21. Chebi:9329

22. Solfadossina

23. 4-amino-n-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide

24. Sulfadoxine-d3

25. Ro-44393

26. 88463u4sm5

27. Wr-4073

28. Ncgc00016612-01

29. Orthosulfin

30. J21.373j

31. Cas-2447-57-6

32. Solfadossina [dcit]

33. Dsstox_cid_3608

34. Dsstox_rid_77106

35. Dsstox_gsid_23608

36. Sulfadoxinum [inn-latin]

37. Sulfadoxina [inn-spanish]

38. 4-amino-n-[5,6-bis(methyloxy)pyrimidin-4-yl]benzenesulfonamide

39. Wr 4873

40. Sr-05000001523

41. Einecs 219-504-9

42. N1-(5,6-dimethoxy-4-pyrimidinyl)sulfanilamide

43. Brn 0625453

44. Sulfadoxine (jan/usp/inn)

45. Unii-88463u4sm5

46. Sanasil: Sulfadoxine: Sulformetoxin

47. Mfcd00792890

48. N(sup 1)-(5,6-dimethoxy-4-pyrimidinyl)sulfanilamide

49. Wr 4073

50. Sulfadoxine [usan:usp:inn:ban:jan]

51. Sulfadoxine [mi]

52. Prestwick0_001094

53. Prestwick1_001094

54. Prestwick2_001094

55. Prestwick3_001094

56. Sulfadoxine [inn]

57. Sulfadoxine [jan]

58. Sulfadoxine [usan]

59. Sulfadoxine [vandf]

60. Chembl1539

61. Sulfadoxine [mart.]

62. Schembl41069

63. Bspbio_001168

64. Sulfadoxine [usp-rs]

65. Sulfadoxine [who-dd]

66. Sulfadoxine [who-ip]

67. 5-25-13-00306 (beilstein Handbook Reference)

68. Mls002154150

69. Spbio_003054

70. Bpbio1_001286

71. Zinc2094

72. Sulfadoxin, >=95% (tlc)

73. Dtxsid6023608

74. Gtpl10173

75. Sulfadoxine [orange Book]

76. Hms1571k10

77. Hms2090p07

78. Hms2094c19

79. Hms2098k10

80. Hms2230e05

81. Hms3371i15

82. Hms3715k10

83. Pharmakon1600-01506086

84. Sulfadoxine [ep Monograph]

85. Sulfadoxine [usp Monograph]

86. Hy-b0439

87. Sulfadoxinum [who-ip Latin]

88. Tox21_110523

89. Bbl023187

90. Fansidar Component Sulfadoxine

91. Nsc759319

92. S2511

93. Stl356042

94. Akos015897281

95. Sulfadoxin 100 Microg/ml In Methanol

96. Tox21_110523_1

97. Ac-8428

98. Ccg-213610

99. Db01299

100. Ks-5334

101. Nsc 759319

102. Sulfadoxine Component Of Fansidar

103. Ncgc00016612-02

104. Ncgc00016612-04

105. Ncgc00016612-05

106. Sulfadoxine 1000 Microg/ml In Methanol

107. Smr000857259

108. Sbi-0206941.p001

109. Sulfadoxine 100 Microg/ml In Acetonitrile

110. Db-046463

111. Ab00514044

112. Ft-0603610

113. N1-5,6-dimethoxy-4-pyrimidinylsulfanilamide

114. 47s576

115. C07630

116. D00580

117. H10765

118. Sulfadoxin, Vetranal(tm), Analytical Standard

119. Ab00514044-06

120. Ab00514044_07

121. Ab00514044_08

122. A817328

123. Q411557

124. Sr-05000001523-1

125. Sr-05000001523-3

126. W-107313

127. Brd-k55250441-001-03-1

128. Brd-k55250441-001-06-4

129. Sulfadoxin, Certified Reference Material, Tracecert(r)

130. 4-amino-n-(5,6-dimethoxy-4-pyrimidinyl)benzenesulfonamide;

131. 4-azanyl-n-(5,6-dimethoxypyrimidin-4-yl)benzenesulfonamide

132. Sulfadoxine, European Pharmacopoeia (ep) Reference Standard

133. Sulfadoxine, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₄N₄O₄S
Molecular Weight	310.33 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	310.07357611 g/mol
Monoisotopic Mass	310.07357611 g/mol
Topological Polar Surface Area	125 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	420
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

Sulfadoxine is used in combination with pyrimethamine for the treatment or prevention of malaria. It can also be used to treat various infections in livestock as well. Sulfadoxine and pyrimethamine is indicated for the treatment of Plasmodium falciparum malaria in those patients in whom chloroquine resistance is suspected.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sulfadoxine helps inhibit the enzyme dihydropteroate synthetase which is an enzyme necessary in the conversion of PABA to folic acid. As folic acid is vital to the synthesis, repair, and methylation of DNA which is vital to cell growth in Plasmodium falciparum. With this vital nutrient lacking, the parasite has difficulty in reproducing.

5.2 MeSH Pharmacological Classification

Anti-Infective Agents, Urinary

Substances capable of killing agents causing urinary tract infections or of preventing them from spreading. (See all compounds classified as Anti-Infective Agents, Urinary.)

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.)

Antimalarials

Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

SULFADOXINE

5.3.2 FDA UNII

88463U4SM5

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Sulfonamides

5.4 Mechanism of Action

Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.

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