|Other names||1,1-(Dichlorodiphenyl)-2,2-dichloroethane; o,p'-DDD|
|Elimination half-life||18 to 159 days|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||320.04 g/mol g·mol−1|
|3D model (JSmol)|
|Melting point||76 to 78 °C (169 to 172 °F)|
Mitotane, sold under the brand name Lysodren, is a steroidogenesis inhibitor and cytostatic antineoplastic medication which is used in the treatment of adrenocortical carcinoma and Cushing's syndrome. It is a derivative of the early insecticide DDT and an isomer of p,p'-DDD, and is also known as 1,1-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD).
Mitotane has been produced by Bristol Myers Squibb SpA but it is marketed as an orphan drug for adrenocortical carcinoma due to the small number of patients in need of it. Its main use is in those patients who have persistent disease despite surgical resection, those who are not surgical candidates, or those who have metastatic disease. A 2007 study of 177 patients shows a significant increase in the recurrence-free interval after radical surgery followed by mitotane when compared to surgery alone [edit: this sentence is misleading in that it does not indicate that the study cited was derived from retrospective data (1985-2005) across different health systems with varying standards of care. ]. The drug is also sometimes used in the treatment of Cushing's syndrome.
The use of mitotane is unfortunately limited by side effects, which, as reported by Schteinberg et al., include anorexia and nausea (88%), diarrhea (38%), vomiting (23%), decreased memory and ability to concentrate (50%), rash (23%), gynecomastia (50%), arthralgia (19%), and leukopenia (7%).
Mitotane is an inhibitor of the adrenal cortex. It acts as an inhibitor of cholesterol side-chain cleavage enzyme (P450scc, CYP11A1), and also of 11β-hydroxylase (CYP11B1), 18-hydroxylase (aldosterone synthase, CYP11B2), and 3β-hydroxysteroid dehydrogenase (3β-HSD) to a lesser extent. In addition, mitotane has direct and selective cytotoxic effects on the adrenal cortex, via an unknown mechanism, and thereby induces permanent adrenal atrophy similarly to DDD.
Society and culture
Mitotane is also used to treat Cushing's disease (pituitary-dependent Cushing's syndrome) in dogs. The medication is used in the controlled destruction of adrenal tissue, leading to a decrease in cortisol production.
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- Information from PubChem
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- Government of Canada: Benzene, 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]- (Mitotane)
- Environment Canada & Health Canada: RISK MANAGEMENT SCOPE for Benzene, 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]- (Mitotane), 2013