Structural Formula Vector Image
Title: Sulfamidochrysoidine
CAS Registry Number: 103-12-8
CAS Name: 4-[(2,4-Diaminophenyl)azo]benzenesulfonamide
Additional Names: 2,4-diaminoazobenzene-4¢-sulfonamide; 4¢-sulfamyl-2,4-diaminoazobenzene
Molecular Formula: C12H13N5O2S
Molecular Weight: 291.33
Percent Composition: C 49.47%, H 4.50%, N 24.04%, O 10.98%, S 11.01%
Literature References: Prototype compd leading to the development of sulfonamide antibacterials. Prepn: F. Mietzsch, J. Klarer, DE 607537 (1935 to I. G. Farbenind.); eidem, US 2085037 (1937 to Winthrop). Antibacterial activity in vivo: G. Domagk, Dtsch. Med. Wochenschr. 61, 573 (1935); (for English translation see Rev. Infect. Dis. 8, 163 (1986)). Identification of sulfanilamide as active metabolite: J. Tréfouel et al., C.R. Seances Soc. Biol. Ses Fil. 120, 756 (1935); L. Colebrook et al., Lancet 2, 1323 (1936). Polymorphic forms in commercial prepns: L. Kofler, A. Kofler, Monatsh. Chem. 81, 321 (1950). Use to visualize carbonic anhydrase during isoelectric focusing in polyacrylamide gels: W. Siffert et al., J. Biochem. Biophys. Methods 8, 331 (1983). Historical review: M. H. Bickel, Gesnerus 45, 67-86 (1988).
Derivative Type: Hydrochloride
CAS Registry Number: 33445-35-1
Trademarks: Prontosil; Prontosil flavum; Prontosil rubrum; Rubiazol I; Septosan (Mallard); Streptozon
Molecular Formula: C12H13N5O2S.HCl
Molecular Weight: 327.79
Percent Composition: C 43.97%, H 4.30%, N 21.37%, O 9.76%, S 9.78%, Cl 10.82%
Properties: Orange-red crystals, mp 248-250°. One gram dissolves in 400 ml water; much more sol in hot water. Sol in alcohol, acetone, fats, oils.
Melting point: mp 248-250°
Use: Specific stain for carbonic anhydrase in polyacrylamide gels.
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Synthetic); Sulfonamides.

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