Mitotane

Mitotane
Clinical data
Trade names	Lysodren
Other names	1,1-(Dichlorodiphenyl)-2,2-dichloroethane; o,p'-DDD
AHFS/Drugs.com	Monograph
MedlinePlus	a608050
License data	US DailyMed: Mitotane;
Routes of; administration	By mouth
ATC code	L01XX23 (WHO) ;
Legal status
Legal status	CA: ℞-only; US: WARNING; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	40%
Protein binding	6%
Elimination half-life	18–159 days
Identifiers
	IUPAC name (RS)-1-chloro-2-[2,2-dichloro-1-(4-chlorophenyl)-ethyl]-benzene;
CAS Number	53-19-0 ;
PubChem CID	4211;
IUPHAR/BPS	6957;
DrugBank	DB00648 ;
ChemSpider	4066 ;
UNII	78E4J5IB5J;
KEGG	D00420 ;
ChEMBL	ChEMBL1670 ;
CompTox Dashboard (EPA)	DTXSID9020372 ;
ECHA InfoCard	100.000.152
Chemical and physical data
Formula	C14H10Cl4
Molar mass	320.03 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
Melting point	76 to 78 °C (169 to 172 °F)
	SMILES Clc1ccccc1C(c2ccc(Cl)cc2)C(Cl)Cl;
	InChI InChI=1S/C14H10Cl4/c15-10-7-5-9(6-8-10)13(14(17)18)11-3-1-2-4-12(11)16/h1-8,13-14H ; Key:JWBOIMRXGHLCPP-UHFFFAOYSA-N ;
	(verify)

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.^[4]^[5]^[6]^[7] It is a derivative of the early insecticide DDT and an isomer of p,p'-DDDTooltip dichlorodiphenyldichloroethane (4,4'-dichlorodiphenyldichloroethane) and is also known as 2,4'-(dichlorodiphenyl)-2,2-dichloroethane (o,p'-DDD).^[8]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
^ "Lysodren EPAR". European Medicines Agency. 12 June 2002. Retrieved 27 June 2024.
^ Cavagnini F, Giraldi FP (18 May 2010). "Adrenal Causes of Hypercortisolism". In Jameson JL, De Groot LJ (eds.). Endocrinology - E-Book: Adult and Pediatric. Elsevier Health Sciences. pp. 1888–. ISBN 978-1-4557-1126-0.
^ Hahner S, Fassnacht M (April 2005). "Mitotane for adrenocortical carcinoma treatment". Current Opinion in Investigational Drugs. 6 (4): 386–394. PMID 15898346.
^ Dang C, Trainer PJ (1 October 2010). "Medical Management of Cushing's Syndrome". In Bronstein MD (ed.). Cushing's Syndrome: Pathophysiology, Diagnosis and Treatment. Springer Science & Business Media. pp. 156–. ISBN 978-1-60327-449-4.
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 382–. ISBN 978-1-4757-2085-3.
^ "Mitotane". PubChem. U.S. National Library of Medicine.