684. Anthralin

Nomenclature

CAS number: 1143-38-0
1,8-Dihydroxy-9(10H)-anthracenone; 1,8-dihydroxyanthrone; dithranol; Anthraforte (Stiefel); Anthranol (Stiefel); Anthrascalp (Stiefel); Antraderm (Protea); Cignolin (Bayer); Dithrocream (Dermal); Drithocreme (Dermik); Dritho-Scalp (Dermik); Micanol (Bioglan); Psoradrate (Procter & Gamble); Psoriderm (Istoria).
C14H10O3; mol wt 226.23.
C 74.33%, H 4.46%, O 21.22%.

Description and references

Prepn: Y. Hirosé, Ber. 45, 2474 (1912); K. Zahn, H. Koch, ibid. 71B, 172 (1938). Revised structure: H. M. Avdovich, G. A. Neville, Can. J. Spectrosc. 25, 110 (1980); F. R. Ahmed, Acta Crystallogr. B36, 3184 (1980). Historical review: R. E. Ashton et al., J. Am. Acad. Dermatol. 9, 173-192 (1983). Review of mechanism of action: L. Kemény et al., Skin Pharmacol. 3, 1-20 (1990); of clinical pharmacology and efficacy in psoriasis: G. Mahrle, Clin. Dermatol. 15, 723-737 (1997).

Chemical structure

Properties

Lemon yellow leaflets or needles from ligroin, mp 176-181°. Sol in chloroform, acetone, benzene and in sols of alkali hydroxides. Slightly sol in alcohol, ether, glacial acetic acid. Sol in dil NaOH with yellow color and green fluorescence, becoming orange-red on exposure to air. Practically insol in water.

Therapeutic Category

Antipsoriatic.

Keywords

Antipsoriatic