Structure via PubChem · Public domain (PubChem)
(RS)-mitotane
Sign in to saveAlso known as o,p′-DDD
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 (4,4'-dichlorodiphenyldichloroethane) and is also known as '''2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD''').
Chemical data
- Formula
- C14H10Cl4
- Molecular weight
- 320 g/mol
- IUPAC name
- 1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]benzene
- SMILES
- C1=CC=C(C(=C1)C(C2=CC=C(C=C2)Cl)C(Cl)Cl)Cl
- InChIKey
- JWBOIMRXGHLCPP-UHFFFAOYSA-N
- XLogP
- 6.2
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Research
3 papers- The effect of mitotane on viability, steroidogenesis and gene expression in NCI‑H295R adrenocortical cells.Molecular medicine reports · 2013
- Survival and prognostic factors for adrenocortical carcinoma: a single institution experience.BMC urology · 2015
- Determination of chiral ratio of o,p-DDT and o,p-DDD pesticides on polysaccharides chiral stationary phases by HPLC under reversed-phase mode.Environmental toxicology · 2002
via PubMed
Wikidata facts
- Mass
- 317.95366104
Show 3 more facts
- chemical formula
- C₁₄H₁₀Cl₄
- canonical SMILES
- C1=CC=C(C(=C1)C(C2=CC=C(C=C2)Cl)C(Cl)Cl)Cl
- Commons category
- Mitotane
via Wikidata · CC0
~4 min read
Article
13 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Pharmacodynamics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Veterinary use
- References
- Further reading
- External links
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 (4,4'-dichlorodiphenyldichloroethane) and is also known as '''2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD''').
==Medical uses== Mitotane has been produced by Bristol Myers Squibb 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. In a 2007 retrospective study of 177 patients from 1985 to 2005 showed a significant increase in the recurrence-free interval after radical surgery followed by mitotane when compared to surgery alone. The drug is also sometimes used in the treatment of Cushing's syndrome.