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SML1885

Sigma-Aldrich

Mitotane

≥98% (HPLC)

Synonyme(s) :

1-(2-Chlorophenyl)-1-(4-chlorophenyl)-2,2-dichloroethane, 1-Chloro-2-[2,2-dichloro-1-(4-chlorophenyl)ethyl]-benzene, 2,4′-DDD, o,p′-DDD

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About This Item

Formule empirique (notation de Hill):
C14H10Cl4
Numéro CAS:
53-19-0
Poids moléculaire :
320.04
Numéro CE :
200-166-6
Numéro MDL:
MFCD00000850
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 20 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

ClC1=C(C(C(Cl)Cl)C2=CC=C(Cl)C=C2)C=CC=C1

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

Clé InChI

JWBOIMRXGHLCPP-UHFFFAOYSA-N

Actions biochimiques/physiologiques

Mitotane is a selective inhibitor of sterol-Oacyl-transferase 1 (SOAT1), also known as ACAT1, (acyl-coenzyme A cholesterol acyltransferase). Mitotane inhibition of SOAT1 in adrenocortical carcinoma cells decreased the formation of cholesteryl esters, which increased free cholesterol levels and caused endoplasmic reticulum (ER) stress, the unfolded protein response, and eventually apoptosis.

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Warning

Mentions de danger

H351

Classification des risques

Carc. 2

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Matthias Kroiss et al.
Hormones & cancer, 7(5-6), 345-355 (2016-11-01)
Mitotane is the only drug approved for treatment of the orphan disease adrenocortical carcinoma (ACC) and was recently shown to be the first clinically used drug acting through endoplasmic reticulum (ER)-stress induced by toxic lipids. Since mitotane has limited clinical
S Beloribi-Djefaflia et al.
Oncogenesis, 5, e189-e189 (2016-01-26)
Many human diseases, including metabolic, immune and central nervous system disorders, as well as cancer, are the consequence of an alteration in lipid metabolic enzymes and their pathways. This illustrates the fundamental role played by lipids in maintaining membrane homeostasis
Xiangyu Li et al.
iScience, 24(7), 102722-102722 (2021-07-15)
Clear cell renal cell carcinoma (ccRCC) is the most common histological type of kidney cancer and has high heterogeneity. Stratification of ccRCC is important since distinct subtypes differ in prognosis and treatment. Here, we applied a systems biology approach to
Silviu Sbiera et al.
Endocrinology, 156(11), 3895-3908 (2015-08-26)
Adrenocortical carcinoma (ACC) is a rare malignancy that harbors a dismal prognosis in advanced stages. Mitotane is approved as an orphan drug for treatment of ACC and counteracts tumor growth and steroid hormone production. Despite serious adverse effects, mitotane has
Christina Bothou et al.
Cancers, 13(16) (2021-08-28)
Current systemic treatment options for patients with adrenocortical carcinomas (ACCs) are far from being satisfactory. DNA damage/repair mechanisms, which involve, e.g., ataxia-telangiectasia-mutated (ATM) and ataxia-telangiectasia/Rad3-related (ATR) protein signaling or ribonucleotide reductase subunits M1/M2 (RRM1/RRM2)-encoded ribonucleotide reductase (RNR) activation, commonly contribute

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