mitotane indications/contra

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

Drug dosage:

None

Approvals:

DateAgencyCompanyOrphan
July 8, 1970 FDA BRISTOL MYERS SQUIBB

FDA Adverse Event Reporting System

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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 101.64 52.95 17 179 1904 3383759
Drug level above therapeutic 62.51 52.95 10 186 835 3384828
Accidental exposure to product 56.47 52.95 12 184 4780 3380883

Pharmacologic Action:

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

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Carcinoma in situ of adrenal cortex indication 92526009
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
Hypercortisolism off-label use 47270006 DOID:3947

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:

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

External reference:

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IDSource
4018140 VUID
N0000146477 NUI
C0026256 UMLSCUI
6957 IUPHAR_LIGAND_ID
D00420 KEGG_DRUG
78E4J5IB5J UNII
2597 INN_ID
DB00648 DRUGBANK_ID
4018140 VANDF
7004 RXNORM
26288002 SNOMEDCT_US
404865004 SNOMEDCT_US
5123 MMSL
d01378 MMSL
N0000005720 NDFRT
N0000146477 NDFRT
002669 NDDF
4211 PUBCHEM_CID
CHEMBL1670 ChEMBL_ID
D008939 MESH_DESCRIPTOR_UI
CHEBI:6954 CHEBI

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
LYSODREN HUMAN PRESCRIPTION DRUG LABEL 1 0015-3080 TABLET 500 mg ORAL NDA 18 sections