6216. Mitotane

Nomenclature

CAS number: 53-19-0
1-Chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene; 1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane; 2-(2-chlorophenyl)-2-(4-chlorophenyl)-1,1-dichloroethane; 2,4′-dichlorodiphenyldichloroethane; 2,2-bis(2-chlorophenyl-4-chlorophenyl)-1,1-dichloroethane; o,p′-DDD; CB-313; Lysodren (BMS).
C14H10Cl4; mol wt 320.04.
C 52.54%, H 3.15%, Cl 44.31%.

Description and references

Constituent of commercial DDD, q.v., which contains about 10% of this o,p′-isomer. Prepn from 2,2-dichloro-1-(o-chlorophenyl)ethanol with chlorobenzene in presence of H2SO4: H. L. Haller et al., J. Am. Chem. Soc. 67, 1591 (1945). Isoln from technical grade DDD: Cueto, Brown, Endocrinology 62, 326 (1958). HPLC determn in plasma: A. Andersen et al., Ther. Drug Monit. 21, 355 (1999). Use in treatment of hyperadrenocorticism in dogs: P. P. Kintzer, M. E. Peterson, J. Am. Vet. Med. Assoc. 205, 54 (1994). Review of pharmacology and clinical efficacy in adrenocortical carcinoma: M. L. Gutierrez, S. T. Crooke, Cancer Treat. Rev. 7, 49-55 (1980); S. Hahner, M. Fassnacht, Curr. Opin. Investig. Drugs 6, 386-394 (2005).

Chemical structure

Properties

Crystals from pentane or methanol, mp 76-78°. Slight aromatic odor. Sol in ethanol, isooctane, carbon tetrachloride, ether, hexane, fixed oils, fats. Practically insol in water.

Therapeutic Category

Antineoplastic.

Therapeutic Category (Veterinary)

In treatment of pituitary-dependent hyperadrenocorticism in dogs.

Keywords

Antineoplastic (Hormonal); Antiadrenals