Title: Dapsone
CAS Registry Number: 80-08-0
CAS Name: 4,4¢-Sulfonylbisbenzeneamine
Additional Names: 4,4¢-sulfonyldianiline; bis(4-aminophenyl)sulfone; 4,4¢-diaminodiphenyl sulfone; DDS; diaphenylsulfone; DADPS
Manufacturers' Codes: 1358F
Trademarks: Avlosulfon (Wyeth-Ayerst); Croysulfone; Diphenasone; Disulone (Specia); Dumitone; Eporal; Novophone; Sulfona-Mae; Sulphadione; Udolac (Mallinckrodt)
Molecular Formula: C12H12N2O2S
Molecular Weight: 248.30
Percent Composition: C 58.05%, H 4.87%, N 11.28%, O 12.89%, S 12.91%
Literature References: Prepn: FR 829926 (1938 to I. G. Farbenind.), C.A. 33, 1761 (1939); Buckles, J. Chem. Educ. 31, 36 (1954); Ferry et al., Org. Synth. coll. vol. III, 239 (1955). Antibacterial action and metabolism: J. Francis, A. Spinks, Br. J. Pharmacol. 5, 565 (1950). Mechanism of toxic action: Wu, DuBois, Arch. Int. Pharmacodyn. Ther. 183, 36 (1970). Comprehensive description: C. E. Orzech et al., Anal. Profiles Drug Subs. 5, 87-114 (1976). Review of pharmacology and therapeutic use: J. Uetrecht, Clin. Dermatol. 7, 111-120 (1989). Clinical trial with chlorproguanil, q.v., in drug-resistant malaria: T. Mutabingwa et al., Lancet 358, 1218 (2001).
Properties: Crystals from 95% ethanol. mp 175-176° (also a higher melting form, mp 180.5°). pKb 13.0. Soluble in alcohol, methanol, acetone, dil hydrochloric acid. Practically insol in water.
Melting point: mp 175-176° (also a higher melting form, mp 180.5°)
pKa: pKb 13.0
Use: Hardening agent in the curing of epoxy resins.
Therap-Cat: Antibacterial (leprostatic); in treatment of dermatitis herpetiformis.
Therap-Cat-Vet: Antibacterial; coccidostat.
Keywords: Antibacterial (Synthetic); Sulfones; Antibacterial (Leprostatic); Dermatitis Herpetiformis Suppressant. |