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Substance Name: Mitotane [USAN:USP:INN:BAN:JAN]
RN: 53-19-0
UNII: 78E4J5IB5J
InChIKey: JWBOIMRXGHLCPP-UHFFFAOYSA-N

Note

  • A derivative of the insecticide DICHLORODIPHENYLDICHLOROETHANE that specifically inhibits cells of the adrenal cortex and their production of hormones. It is used to treat adrenocortical tumors and causes CNS damage, but no bone marrow depression.

Molecular Formula

  • C14-H10-Cl4

Molecular Weight

  • 320.045
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Antineoplastic
  • Antineoplastic Agents
  • Antineoplastic Agents, Hormonal
  • Drug / Therapeutic Agent
  • Human Data
  • Insecticide
  • Mutation Data
  • Reproductive Effect
  • Tumor Data

Superlist Classification Codes

  • 2007 CERCLA Priority List, Rank: 151
  • 2011 CERCLA Priority List, Rank: 87
  • Overall Carcinogenic Evaluation: Group 2B

Names and Synonyms

Name of Substance

  • Mitotane
  • Mitotane [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Mitotane

Synonyms

  • (+-)-1,1-Dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
  • 1,1-Dichloro-2,2-bis(2,4'-dichlorophenyl)ethane
  • 1,1-Dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)ethane
  • 1,1-Dichloro-2-(p-chlorophenyl)-2-(o-chlorophenyl)ethane
  • 1-Chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)benzene
  • 2,2-Bis(2-chlorophenyl-4-chlorophenyl)-1,1-dichloroethane
  • 2,4'-Ddd
  • 2,4'-Dichlorodiphenyldichloroethane
  • 2,4'-Dichlorophenyldichlorethane
  • 2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1-dichloroethane
  • 2-(o-Chlorophenyl)-2-(p-chlorophenyl)-1,1-dichloroethane
  • 4-05-00-01883 (Beilstein Handbook Reference)
  • AI3-07575
  • Benzene, 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)-
  • Benzene, 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)-, (+-)-
  • BRN 2056007
  • CB 313
  • CB313
  • CCRIS 4397
  • Chloditan
  • Chlodithan
  • Chlodithane
  • EINECS 200-166-6
  • Ethane, 1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)-
  • Ethane, 2-(o-chlorophenyl)-2-(p-chlorophenyl)-1,1-dichloro-
  • HSDB 3240
  • Khlodithan
  • Lysodren
  • Mitotan
  • Mitotane
  • Mitotano
  • Mitotano [INN-Spanish]
  • Mitotanum
  • Mitotanum [INN-Latin]
  • NCI-C04933
  • NSC 38721
  • o,p'-DDD
  • o,p'-Dichlorodiphenyldichloroethane
  • o,p-TDE
  • UNII-78E4J5IB5J

Systematic Names

  • 2-(2-Chlorophenyl)-2-(4-chlorophenyl)-1,1-dichloroethane
  • Benzene, 1-chloro-2-(2,2-dichloro-1-(4-chlorophenyl)ethyl)-
  • Ethane, 1,1-dichloro-2-(o-chlorophenyl)-2-(p-chlorophenyl)- (8CI)
  • Ethane, 2-(o-chlorophenyl)-2-(p-chlorophenyl)-1,1-dichloro-
  • Mitotane

Superlist Names

  • DDD, o,p'-
  • o,p'-TDE

Registry Numbers

CAS Registry Number

  • 53-19-0

FDA UNII

  • 78E4J5IB5J

System Generated Number

  • 0000053190

Structure Descriptors

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

InChIKey

JWBOIMRXGHLCPP-UHFFFAOYSA-N

Smiles

C(c1c(cccc1)Cl)(c1ccc(cc1)Cl)C(Cl)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral > 5gm/kg (5000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 309, 1984.
man TDLo oral 17gm/kg/35W (17000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Cancer Vol. 42, Pg. 2177, 1978.
mouse LD50 oral > 4gm/kg (4000mg/kg)   Pharmaceutical Chemistry Journal Vol. 11, Pg. 1298, 1977.
rat LD50 oral > 5gm/kg (5000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 26, Pg. 309, 1984.
women TDLo oral 800mg/kg/4D (800mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Cancer Vol. 42, Pg. 2177, 1978.
women TDLo oral 11gm/kg/15W (11000mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BLOOD: NORMOCYTIC ANEMIA

BLOOD: PIGMENTED OR NUCLEATED RED BLLOD CELLS
Cancer Vol. 42, Pg. 2177, 1978.
women TDLo oral 14gm/kg/22W (14000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Cancer Vol. 42, Pg. 2177, 1978.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 77 deg C   EXP
log P (octanol-water) 5.870 (none)   EST
Water Solubility 0.1 mg/L 25 EXP
Vapor Pressure 1.94E-06 mm Hg 30 EXP
Henry's Law Constant 8.17E-06 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.34E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.