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Sulfalene

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Also known as: 152-47-6, Sulfamethoxypyrazine, Sulfametopyrazine, Sulfamethopyrazine, Sulfalen, 4-amino-n-(3-methoxypyrazin-2-yl)benzenesulfonamide

Molecular Formula

C₁₁H₁₂N₄O₃S

Molecular Weight

280.31 g/mol

InChI Key

KXRZBTAEDBELFD-UHFFFAOYSA-N

FDA UNII

T6BL4ZC15G

Long-acting plasma-bound sulfonamide used for respiratory and urinary tract infections and also for malaria.

1 2D Structure

Sulfalene

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-amino-N-(3-methoxypyrazin-2-yl)benzenesulfonamide

2.1.2 InChI

InChI=1S/C11H12N4O3S/c1-18-11-10(13-6-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)

2.1.3 InChI Key

KXRZBTAEDBELFD-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=NC=CN=C1NS(=O)(=O)C2=CC=C(C=C2)N

2.2 Other Identifiers

2.2.1 UNII

T6BL4ZC15G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Kelfizine

2. Longum

3. Sulfamethopyrazine

4. Sulfamethoxypyrazine

5. Sulfametopyrazine

6. Sulfapyrazinmethoxine

7. Sulphalene

8. Sulphametopyrazine

2.3.2 Depositor-Supplied Synonyms

1. 152-47-6

2. Sulfamethoxypyrazine

3. Sulfametopyrazine

4. Sulfamethopyrazine

5. Sulfalen

6. 4-amino-n-(3-methoxypyrazin-2-yl)benzenesulfonamide

7. Kelfizine

8. Longum

9. Sulfapyrazinemethoxine

10. Sulfapyrazinemethoxyne

11. Kelfizin

12. Kelfizina

13. Polycidal

14. Dalysep

15. Sulfapyrazinemethoxyine

16. Kelfizine W

17. Smp2

18. 3-methoxy-2-sulfapyrazine

19. 2-sulfanilamido-3-methoxypyrazine

20. 3-methoxy-2-sulfanilamidopyrazine

21. Farmitalia 204/122

22. 3-methoxypyrazine Sulfanilamide

23. 2-methoxy-3-sulfanilamidopyrazine

24. Nsc-110433

25. N1-(3-methoxypyrazinyl)sulfanilamide

26. Benzenesulfonamide, 4-amino-n-(3-methoxypyrazinyl)-

27. 2-(p-aminobenzenesulfanamide)-3-methoxypyrazine

28. 2-(p-aminobenzenesulfonamido)-3-methoxypyrazine

29. As 18908

30. F.i. 5978

31. Pyrazine, 2-sulfanilamido-3-methoxy-

32. 4-amino-n-(3-methoxypyrazinyl)benzenesulfonamide

33. N1-(3-methoxy-2-pyrazinyl)sulfanilamide

34. N(sup1)-(3-methoxypyrazinyl)sulfanilamide

35. N(sup 1)-(3-methoxypyrazinyl)sulfanilamide

36. 4-amino-n-(3-methoxy-2-pyrazinyl)-benzenesulfonamide

37. Sulfalene(smpz)

38. N(sup1)-(3-methoxy-2-pyrazinyl)sulfanilamide

39. Sulfalene (usan)

40. N(sup 1)-(3-methoxy-2-pyrazinyl)sulfanilamide

41. As-18908

42. Sulfanilamide, N'-(3-methoxypyrazinyl)-

43. Sulfanilamide, N1-(3-methoxypyrazinyl)-

44. Sulfamethopyrazine (jan)

45. Sulfanilamide, N(sup 1)-(3-methoxypyrazinyl)-

46. Sulfanilamide, N(sup 1)-(3-methoxy-2-pyrazinyl)-

47. T6bl4zc15g

48. Sulfametopyrazine;as-18908

49. Sulfalenum

50. Chebi:32162

51. Solfametopirazina

52. Nsc110433

53. Sulfalene [usan:inn]

54. 4-amino-n-(3-methoxypyrazin-2-yl)benzene-1-sulfonamide

55. Sulfalenum [inn-latin]

56. Solfametopirazina [dcit]

57. Sulfaleno [inn-spanish]

58. Ncgc00160482-01

59. Sulfaleno

60. Sulfalene [usan]

61. Dsstox_cid_26179

62. Dsstox_rid_81410

63. Dsstox_gsid_46179

64. Sulfametoxypyridazin

65. 2-sulfanilamide 3-methoxy-pyrazine

66. Sulfamethopyrazine [jan]

67. 4-amino-n-(3-methoxy-pyrazin-2-yl)-benzenesulfonamide

68. Kelfizina (tn)

69. Cas-152-47-6

70. Smr000011031

71. Fi 5978

72. Wr 4629

73. Einecs 205-804-7

74. Cbmicro_013257

75. Unii-t6bl4zc15g

76. Nsc 110433

77. Brn 0622512

78. Vetkelfizina

79. Policydal

80. N-(3-methoxypyrazin-2-yl)sulfanilamide

81. Sulfalene [inn]

82. Sulfalene [mi]

83. Sulfalene [who-dd]

84. Oprea1_010520

85. Schembl28404

86. 4-amino-n-(3-methoxypyrazinyl)-benzenesulfonamide

87. 5-25-12-00574 (beilstein Handbook Reference)

88. Mls001304101

89. Mls001304170

90. Butadiene Sulfone;3-sulfolene

91. 4-amino-n-(3-methoxypyrazin-2-yl);benzenesulfonamide

92. Zinc2097

93. Sulfalene (sulfamethoxypyrazine)

94. Chembl1525826

95. Dtxsid2046179

96. Gtpl10174

97. Sulfametopyrazine [mart.]

98. Hms2866d06

99. Hms3604l11

100. Bcp30869

101. Hy-a0130

102. Smsf0004129

103. Tox21_111844

104. Wln: T6n Dnj Bo1 Cmswr Dz

105. Ac-750

106. Bbl023067

107. Mfcd00437754

108. S4976

109. Stk386859

110. Akos000538590

111. Tox21_111844_1

112. Cb03172

113. Ccg-112228

114. Cs-8165

115. Db00664

116. Ks-5333

117. Ncgc00160482-02

118. Sulfalene 100 Microg/ml In Acetonitrile

119. Bim-0013167.p001

120. Db-043149

121. Ft-0603363

122. Sulfanilamide, N1-(3-methoxy-2-pyrazinyl)-

123. A16975

124. D01216

125. Sulfalene Sulfamethoxypyrazine Sulfametopyrazine

126. 152s476

127. A809315

128. Sr-01000817374

129. Q-201763

130. Q6577302

131. Sr-01000817374-3

132. Z277559098

133. 4-amino-n-(3-methoxypyrazin-2-yl)benzenesulfonamide;sulfalene

134. Sulfametopyrazine; As-18908; Sulfalene; Sulfaleno;sulfamethoxypyrazine

135. 5175-55-3

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₂N₄O₃S
Molecular Weight	280.31 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	280.06301143 g/mol
Monoisotopic Mass	280.06301143 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	376
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 urinary tract infection and chronic bronchitis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Sulfametopyrazine 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

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.)

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.)

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.)

5.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01E - Sulfonamides and trimethoprim

J01ED - Long-acting sulfonamides

J01ED02 - Sulfalene

5.4 Mechanism of Action

Sulfametopyrazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. Para-aminobenzoic acid (PABA), a substrate of the enzyme is prevented from binding. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

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