mitotane Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antineoplastics, nucleotoxic agents 1820 53-19-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mitotane
  • chloditan
  • chlodithane
  • lysodren
  • mitotan
  • opeprim
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 weight: 320.03
  • Formula: C14H10Cl4
  • CLOGP: 6.06
  • LIPINSKI: 1
  • HAC: 0
  • HDO: 0
  • TPSA:
  • ALOGS: -7.53
  • ROTB: 3

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BA (Bioavailability) 40 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
July 8, 1970 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Adrenal insufficiency 81.78 50.05 23 867 14806 53333370
Adrenocortical carcinoma 63.93 50.05 8 882 52 53348124
Drug clearance increased 59.61 50.05 8 882 95 53348081

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Adrenal insufficiency 81.88 43.52 21 418 11947 32501140
Adrenocortical carcinoma 60.28 43.52 7 432 28 32513059

Pharmacologic Action:

SourceCodeDescription
ATC L01XX23 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Other antineoplastic agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D018931 Antineoplastic Agents, Hormonal
FDA MoA N0000185506 Cytochrome P450 3A4 Inducers

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Carcinoma in situ of adrenal cortex indication 92526009
Hypercortisolism off-label use 47270006
Shock contraindication 27942005
Disease of liver contraindication 235856003 DOID:409
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Breastfeeding (mother) contraindication 413712001
Traumatic injury contraindication 417746004
CNS Toxicity contraindication

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Cytochrome P450 11B1, mitochondrial Enzyme INHIBITOR WOMBAT-PK CHEMBL
Cholesterol side-chain cleavage enzyme, mitochondrial Enzyme INHIBITOR CHEMBL CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 6.09 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 5.51 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.19 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 5.56 DRUG MATRIX
Adenosine receptor A3 GPCR Ki 5.38 DRUG MATRIX
Adrenodoxin, mitochondrial Unclassified WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Ki 6.10 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.80 DRUG MATRIX

External reference:

IDSource
4018140 VUID
N0000146477 NUI
D00420 KEGG_DRUG
4018140 VANDF
C0026256 UMLSCUI
CHEBI:6954 CHEBI
CHEMBL1670 ChEMBL_ID
DB00648 DRUGBANK_ID
D008939 MESH_DESCRIPTOR_UI
4211 PUBCHEM_CID
6957 IUPHAR_LIGAND_ID
2597 INN_ID
78E4J5IB5J UNII
204257 RXNORM
1449 MMSL
5123 MMSL
d01378 MMSL
002669 NDDF
26288002 SNOMEDCT_US
404865004 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Lysodren HUMAN PRESCRIPTION DRUG LABEL 1 76336-080 TABLET 500 mg ORAL NDA 24 sections