2822. Dapsone

Nomenclature

CAS number: 80-08-0
4,4′-Sulfonylbisbenzeneamine; 4,4′-sulfonyldianiline; bis(4-aminophenyl)sulfone; 4,4′-diaminodiphenyl sulfone; DDS; diaphenylsulfone; DADPS; 1358F; Avlosulfon (Wyeth-Ayerst); Croysulfone; Diphenasone; Disulone (Specia); Dumitone; Eporal; Novophone; Sulfona-Mae; Sulphadione; Udolac (Mallinckrodt).
C12H12N2O2S; mol wt 248.30.
C 58.05%, H 4.87%, N 11.28%, O 12.89%, S 12.91%.

Description and 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).

Chemical structure

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.

Use

Hardening agent in the curing of epoxy resins.

Therapeutic Category

Antibacterial (leprostatic); in treatment of dermatitis herpetiformis.

Therapeutic Category (Veterinary)

Antibacterial; coccidostat.

Keywords

Antibacterial (Synthetic); Sulfones; Antibacterial (Leprostatic); Dermatitis Herpetiformis Suppressant