Mitotane

Structural formula
	( R ) shape (left) and ( S ) shape (right)
General
Non-proprietary name	Mitotane
other names	( RS ) -1,1-dichloro-2- (2-chlorophenyl) -2- (4-chlorophenyl) ethane; ( RS ) -2- ( o -chlorophenyl) -2- ( p -chlorophenyl) -1,1-dichloroethane; 2,4'-DDD; Choditans; o , p ′ -TDD;
Molecular formula	C 14 H 10 Cl 4
Brief description	white solid
External identifiers / databases
EC number	200-166-6
ECHA InfoCard	100,000,152
PubChem	4211
DrugBank	DB00648
Wikidata	Q417465
Drug information
ATC code	Q L01XX23
properties
Molar mass	320.04 g · mol -1
Physical state	firmly
density	1.39 g cm −3
Melting point	76-78 ° C
Vapor pressure	0.26 m Pa (30 ° C)
solubility	0.1 mg l −1 in water , soluble in ethanol , isooctane and carbon tetrachloride
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 351
	P: 281
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mitotane is a drug that, as a cytostatic, selectively inhibits cell division in the adrenal cortex . It is used in human medicine for inoperable adrenal carcinomas and in veterinary medicine for the treatment of Cushing's syndrome .

Human medicine

In human medicine , tablets with the active ingredient mitotane are approved for the symptomatic treatment of advanced, inoperable , metastatic or recurrent adrenal carcinoma . Since there are few patients with adrenocortical carcinoma, which is considered disease is rare , and the drug was on 12 June 2002 as an orphan medicinal reported ( "orphan drug").

Veterinary medicine

In veterinary medicine , mitotane is used to treat an overactive adrenal gland , known as Cushing's syndrome . It can be used to treat both primary (adrenocortical) and secondary (pituitary) cushing. The active ingredient has a selective cytotoxic effect on the zona fasciculata and zona reticularis of the adrenal cortex and causes necrosis of the glucocorticoid-producing cells and thus a reduced secretion of cortisone . Therapy with mitotane can be permanent and thus restrict the functionality of the adrenal gland. Alternatively, a short-term, high-dose application to destroy the organ is possible; Addison's disease that may be triggered by this is to be treated with medication.

Due to the potential toxicity for humans as well, precautionary measures must be taken when handling mitotane to prevent unintentional ingestion. In addition to wearing rubber gloves during application, this includes the consistent removal of the faeces formed by the animal; Pregnant women should not come into contact with the treated animal.

Mitotane one can also treat alopecia X are applied.

In recent years, mitotane has been almost completely replaced by trilostane . In Germany there is no approved preparation based on mitotane, so that the approved preparation based on trilostane (trade name Vetoryl ) according to Section 56a (2) of the Medicines Act is to be preferred. In addition, Trilostane has a much shorter duration of action and is therefore more tolerable. The use of mitotane in food-producing animals is prohibited as the active ingredient is not listed in Regulation (EU) No. 37/2010 . In Switzerland, too, mitotane is not an active ingredient that is marketable as part of an approved, ready-to-use veterinary medicinal product.

Others

o , p ′ -DDD is contained in technical DDT as a by-product with a proportion of about 0.1%, its isomer p , p ′ -DDD was used as an insecticide in the USA in the 1950s.

Trade names

Lysodren

Web links

Entry to mitotane in Vetpharm
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.

Individual evidence

↑ ^a ^b ^c Data sheet 1- (2-chlorophenyl) -1- (4-chlorophenyl) -2,2-dichloroethane from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).
↑ ^a ^b ^c ^d U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry: Toxicological profile for DDT, DDE and DDD. (PDF; 4.2 MB) , 2002.
^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1073, ISBN 978-0-911910-00-1 .
↑ Lysodren: European Public Assessment Report (EPAR) and Product Information, overview on the website of the European Medicines Agency .
↑ entry to mitotane in Vetpharm, accessed on 24 September 2018th
↑ Meike Horn: Post-clipping alopecia vs. Alopecia X - facts, diagnostics and therapeutic approaches. In: veterinärspiegel Heft 4, 2017, pp. 135–140.
↑ Entry on Trilostane at Vetpharm, accessed on September 26, 2018.
↑ Swissmedic : Approved processes and active substances ( memo of September 27, 2018 in the Internet Archive ) , as of August 31, 2018.

[sigma-1] Data sheet 1- (2-chlorophenyl) -1- (4-chlorophenyl) -2,2-dichloroethane from Sigma-Aldrich , accessed on April 10, 2011 ( PDF ).

[ToxProf-2] U.S. Department of Health and Human Services, Agency for Toxic Substances and Disease Registry: Toxicological profile for DDT, DDE and DDD. (PDF; 4.2 MB) , 2002.

[MerckIndex-3] The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, p. 1073, ISBN 978-0-911910-00-1 .

[epar-4] Lysodren: European Public Assessment Report (EPAR) and Product Information, overview on the website of the European Medicines Agency .

[5] try to mitotane in Vetpharm, accessed on 24 September 2018th

[6] Meike Horn: Post-clipping alopecia vs. Alopecia X - facts, diagnostics and therapeutic approaches. In: veterinärspiegel Heft 4, 2017, pp. 135–140.

[7] Entry on Trilostane at Vetpharm, accessed on September 26, 2018.

[8] Swissmedic : Approved processes and active substances ( memo of September 27, 2018 in the Internet Archive ) , as of August 31, 2018.