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Identification
NameMitotane
Accession NumberDB00648  (APRD00494)
TypeSmall Molecule
GroupsApproved
Description

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. [PubChem]

Structure
Thumb
Synonyms
Lysodren
Mitotan
Mitotane
Mitotano
Mitotanum
Piprine-DDD, O-
External Identifiers
  • CB 313
  • NSC 38721
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Lysodrentablet500 mg/1oralE.R. Squibb & Sons, L.L.C.2009-06-01Not applicableUs
Lysodrentablet500 mgoralBristol Myers Squibb Canada1979-12-31Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
LisodrenBristol-Myers Squibb
OpeprimYakult Honsha
Brand mixturesNot Available
SaltsNot Available
Categories
UNII78E4J5IB5J
CAS number53-19-0
WeightAverage: 320.041
Monoisotopic: 317.953661148
Chemical FormulaC14H10Cl4
InChI KeyInChIKey=JWBOIMRXGHLCPP-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene
SMILES
ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor treatment of inoperable adrenocortical tumours; Cushing's syndrome
PharmacodynamicsMitotane is an oral chemotherapeutic agent indicated in the treatment of inoperable adrenal cortical carcinoma of both functional and nonfunctional types. Mitotane can best be described as an adrenal cytotoxic agent, although it can cause adrenal inhibition, apparently without cellular destruction. The administration of Mitotane alters the extra-adrenal metabolism of cortisol in man; leading to a reduction in measurable 17-hydroxy corticosteroids, even though plasma levels of corticosteroids do not fall. The drug apparently causes increased formation of 6-B-hydroxyl cortisol.
Mechanism of actionIts biochemical mechanism of action is unknown, although data are available to suggest that the drug modifies the peripheral metabolism of steroids as well as directly suppressing the adrenal cortex.
Related Articles
AbsorptionAbout 40% oral Lysodren is absorbed
Volume of distributionNot Available
Protein binding6%
Metabolism

Hepatic and renal

Route of eliminationA variable amount of metabolite (1%-17%) is excreted in the bile and the balance is apparently stored in the tissues.
Half life18-159 days
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9942
Blood Brain Barrier+0.9905
Caco-2 permeable+0.8815
P-glycoprotein substrateNon-substrate0.8053
P-glycoprotein inhibitor INon-inhibitor0.9004
P-glycoprotein inhibitor IINon-inhibitor0.988
Renal organic cation transporterNon-inhibitor0.7959
CYP450 2C9 substrateNon-substrate0.7899
CYP450 2D6 substrateNon-substrate0.818
CYP450 3A4 substrateNon-substrate0.7045
CYP450 1A2 substrateInhibitor0.9542
CYP450 2C9 inhibitorInhibitor0.7241
CYP450 2D6 inhibitorNon-inhibitor0.9349
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorNon-inhibitor0.8629
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8
Ames testNon AMES toxic0.9751
CarcinogenicityNon-carcinogens0.575
BiodegradationNot ready biodegradable0.9596
Rat acute toxicity2.1911 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9221
hERG inhibition (predictor II)Non-inhibitor0.875
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Bristol myers squibb
Packagers
Dosage forms
FormRouteStrength
Tabletoral500 mg/1
Tabletoral500 mg
Prices
Unit descriptionCostUnit
Mitotane powder7.75USD g
Lysodren 500 mg tablet5.13USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point77 °CPhysProp
water solubility0.1 mg/L (at 25 °C)BIGGAR,JW & RIGGS,RI (1974)
logP6Not Available
logS-6.51ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility9.42e-06 mg/mLALOGPS
logP6.08ALOGPS
logP6.11ChemAxon
logS-7.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.97 m3·mol-1ChemAxon
Polarizability29.93 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.84 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
MSMass Spectrum (Electron Ionization)splash10-000i-2690000000-770065ddc57899130a31View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesL01XX23
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (57 KB)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Abiraterone can be decreased when it is combined with Mitotane.
AlfuzosinThe serum concentration of Alfuzosin can be decreased when it is combined with Mitotane.
AlprazolamThe serum concentration of Alprazolam can be decreased when it is combined with Mitotane.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Mitotane.
AmiodaroneThe serum concentration of Amiodarone can be decreased when it is combined with Mitotane.
AmlodipineThe serum concentration of Amlodipine can be decreased when it is combined with Mitotane.
ApixabanThe serum concentration of Apixaban can be decreased when it is combined with Mitotane.
ApremilastThe serum concentration of Apremilast can be decreased when it is combined with Mitotane.
AprepitantThe serum concentration of Aprepitant can be decreased when it is combined with Mitotane.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Mitotane.
ArmodafinilThe serum concentration of Armodafinil can be decreased when it is combined with Mitotane.
ArtemetherThe serum concentration of the active metabolites of Artemether can be reduced when Artemether is used in combination with Mitotane resulting in a loss in efficacy.
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Mitotane.
AtorvastatinThe serum concentration of Atorvastatin can be decreased when it is combined with Mitotane.
AvanafilThe serum concentration of Avanafil can be decreased when it is combined with Mitotane.
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Mitotane.
BedaquilineThe serum concentration of Bedaquiline can be decreased when it is combined with Mitotane.
BenzphetamineThe serum concentration of Benzphetamine can be decreased when it is combined with Mitotane.
BetamethasoneThe serum concentration of Betamethasone can be decreased when it is combined with Mitotane.
BisoprololThe serum concentration of Bisoprolol can be decreased when it is combined with Mitotane.
BoceprevirThe serum concentration of Boceprevir can be decreased when it is combined with Mitotane.
BortezomibThe serum concentration of Bortezomib can be decreased when it is combined with Mitotane.
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Mitotane.
Brentuximab vedotinThe serum concentration of Brentuximab vedotin can be decreased when it is combined with Mitotane.
BrexpiprazoleThe serum concentration of Brexpiprazole can be decreased when it is combined with Mitotane.
BuprenorphineThe serum concentration of Buprenorphine can be decreased when it is combined with Mitotane.
BuspironeThe serum concentration of Buspirone can be decreased when it is combined with Mitotane.
CabazitaxelThe serum concentration of Cabazitaxel can be decreased when it is combined with Mitotane.
CabozantinibThe serum concentration of Cabozantinib can be decreased when it is combined with Mitotane.
CalcitriolThe serum concentration of Calcitriol can be decreased when it is combined with Mitotane.
CannabidiolThe serum concentration of Cannabidiol can be decreased when it is combined with Mitotane.
CarbamazepineThe serum concentration of Carbamazepine can be decreased when it is combined with Mitotane.
CeritinibThe serum concentration of Ceritinib can be decreased when it is combined with Mitotane.
ChlordiazepoxideThe serum concentration of Chlordiazepoxide can be decreased when it is combined with Mitotane.
ChloroquineThe serum concentration of Chloroquine can be decreased when it is combined with Mitotane.
CilostazolThe serum concentration of Cilostazol can be decreased when it is combined with Mitotane.
CitalopramThe serum concentration of Citalopram can be decreased when it is combined with Mitotane.
ClarithromycinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Mitotane.
ClonazepamThe serum concentration of Clonazepam can be decreased when it is combined with Mitotane.
ClorazepateThe serum concentration of Clorazepate can be decreased when it is combined with Mitotane.
ClozapineThe serum concentration of Clozapine can be decreased when it is combined with Mitotane.
CobicistatThe serum concentration of Cobicistat can be decreased when it is combined with Mitotane.
ConivaptanThe serum concentration of Conivaptan can be decreased when it is combined with Mitotane.
CorticotropinThe serum concentration of Corticotropin can be decreased when it is combined with Mitotane.
Cortisone acetateThe serum concentration of Cortisone acetate can be decreased when it is combined with Mitotane.
CrizotinibThe serum concentration of Crizotinib can be decreased when it is combined with Mitotane.
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Mitotane.
Cyproterone acetateThe serum concentration of Cyproterone acetate can be decreased when it is combined with Mitotane.
DaclatasvirThe serum concentration of Daclatasvir can be decreased when it is combined with Mitotane.
DantroleneThe serum concentration of Dantrolene can be decreased when it is combined with Mitotane.
DapsoneThe serum concentration of Dapsone can be decreased when it is combined with Mitotane.
DarifenacinThe serum concentration of Darifenacin can be decreased when it is combined with Mitotane.
DarunavirThe serum concentration of Darunavir can be decreased when it is combined with Mitotane.
DasatinibThe serum concentration of Dasatinib can be decreased when it is combined with Mitotane.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Mitotane.
DexamethasoneThe serum concentration of Dexamethasone can be decreased when it is combined with Mitotane.
DiazepamThe serum concentration of Diazepam can be decreased when it is combined with Mitotane.
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Mitotane.
DiltiazemThe serum concentration of Diltiazem can be decreased when it is combined with Mitotane.
DisopyramideThe serum concentration of Disopyramide can be decreased when it is combined with Mitotane.
DocetaxelThe serum concentration of Docetaxel can be decreased when it is combined with Mitotane.
DoxazosinThe serum concentration of Doxazosin can be decreased when it is combined with Mitotane.
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Mitotane.
DronabinolThe serum concentration of Dronabinol can be decreased when it is combined with Mitotane.
DronedaroneThe serum concentration of Dronedarone can be decreased when it is combined with Mitotane.
EfavirenzThe serum concentration of Efavirenz can be decreased when it is combined with Mitotane.
EliglustatThe serum concentration of Eliglustat can be decreased when it is combined with Mitotane.
ElvitegravirThe serum concentration of Elvitegravir can be decreased when it is combined with Mitotane.
EnzalutamideThe serum concentration of Enzalutamide can be decreased when it is combined with Mitotane.
EplerenoneThe serum concentration of Eplerenone can be decreased when it is combined with Mitotane.
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Mitotane.
ErythromycinThe serum concentration of Erythromycin can be decreased when it is combined with Mitotane.
EscitalopramThe serum concentration of Escitalopram can be decreased when it is combined with Mitotane.
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Mitotane.
Estrone sulfateThe serum concentration of Estropipate can be decreased when it is combined with Mitotane.
EszopicloneThe serum concentration of Eszopiclone can be decreased when it is combined with Mitotane.
EthosuximideThe serum concentration of Ethosuximide can be decreased when it is combined with Mitotane.
EtoposideThe serum concentration of Etoposide can be decreased when it is combined with Mitotane.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Mitotane.
EverolimusThe serum concentration of Everolimus can be decreased when it is combined with Mitotane.
ExemestaneThe serum concentration of Exemestane can be decreased when it is combined with Mitotane.
FelbamateThe serum concentration of Felbamate can be decreased when it is combined with Mitotane.
FelodipineThe serum concentration of Felodipine can be decreased when it is combined with Mitotane.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Mitotane.
FesoterodineThe serum concentration of Fesoterodine can be decreased when it is combined with Mitotane.
FlibanserinThe serum concentration of Flibanserin can be decreased when it is combined with Mitotane.
FludrocortisoneThe serum concentration of Fludrocortisone can be decreased when it is combined with Mitotane.
FlunisolideThe serum concentration of Flunisolide can be decreased when it is combined with Mitotane.
FlurazepamThe serum concentration of Flurazepam can be decreased when it is combined with Mitotane.
FlutamideThe serum concentration of Flutamide can be decreased when it is combined with Mitotane.
FosamprenavirThe serum concentration of Fosamprenavir can be decreased when it is combined with Mitotane.
FosaprepitantThe serum concentration of Fosaprepitant can be decreased when it is combined with Mitotane.
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Mitotane.
GuanfacineThe serum concentration of Guanfacine can be decreased when it is combined with Mitotane.
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Mitotane.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Mitotane.
HydrocortisoneThe serum concentration of Hydrocortisone can be decreased when it is combined with Mitotane.
Hydroxyprogesterone caproateThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Mitotane.
IbrutinibThe serum concentration of Ibrutinib can be decreased when it is combined with Mitotane.
IdelalisibThe serum concentration of Idelalisib can be decreased when it is combined with Mitotane.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be increased when Ifosfamide is used in combination with Mitotane.
ImatinibThe serum concentration of Imatinib can be decreased when it is combined with Mitotane.
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Mitotane.
IrinotecanThe serum concentration of the active metabolites of Irinotecan can be reduced when Irinotecan is used in combination with Mitotane resulting in a loss in efficacy.
IsavuconazoniumThe serum concentration of the active metabolites of Isavuconazonium can be reduced when Isavuconazonium is used in combination with Mitotane resulting in a loss in efficacy.
IsosorbideThe serum concentration of Isosorbide can be decreased when it is combined with Mitotane.
Isosorbide DinitrateThe serum concentration of Isosorbide Dinitrate can be decreased when it is combined with Mitotane.
Isosorbide MononitrateThe serum concentration of Isosorbide Mononitrate can be decreased when it is combined with Mitotane.
IsradipineThe serum concentration of Isradipine can be decreased when it is combined with Mitotane.
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Mitotane.
IvabradineThe serum concentration of Ivabradine can be decreased when it is combined with Mitotane.
IvacaftorThe serum concentration of Ivacaftor can be decreased when it is combined with Mitotane.
IxabepiloneThe serum concentration of Ixabepilone can be decreased when it is combined with Mitotane.
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Mitotane.
LansoprazoleThe serum concentration of Lansoprazole can be decreased when it is combined with Mitotane.
LapatinibThe serum concentration of Lapatinib can be decreased when it is combined with Mitotane.
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Mitotane.
LidocaineThe serum concentration of Lidocaine can be decreased when it is combined with Mitotane.
LinagliptinThe serum concentration of Linagliptin can be decreased when it is combined with Mitotane.
LomitapideThe serum concentration of Lomitapide can be decreased when it is combined with Mitotane.
LosartanThe serum concentration of Losartan can be decreased when it is combined with Mitotane.
LovastatinThe serum concentration of Lovastatin can be decreased when it is combined with Mitotane.
LumefantrineThe serum concentration of Lumefantrine can be decreased when it is combined with Mitotane.
LurasidoneThe serum concentration of Lurasidone can be decreased when it is combined with Mitotane.
MacitentanThe serum concentration of MACITENTAN can be decreased when it is combined with Mitotane.
MaravirocThe serum concentration of Maraviroc can be decreased when it is combined with Mitotane.
Medroxyprogesterone acetateThe serum concentration of Medroxyprogesterone Acetate can be decreased when it is combined with Mitotane.
MefloquineThe serum concentration of Mefloquine can be decreased when it is combined with Mitotane.
MethadoneThe serum concentration of Methadone can be decreased when it is combined with Mitotane.
MethylprednisoloneThe serum concentration of Methylprednisolone can be decreased when it is combined with Mitotane.
MidazolamThe serum concentration of Midazolam can be decreased when it is combined with Mitotane.
MifepristoneThe serum concentration of Mifepristone can be decreased when it is combined with Mitotane.
MirtazapineThe serum concentration of Mirtazapine can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Modafinil can be decreased when it is combined with Mitotane.
NaloxegolThe serum concentration of Naloxegol can be decreased when it is combined with Mitotane.
NateglinideThe serum concentration of Nateglinide can be decreased when it is combined with Mitotane.
NefazodoneThe serum concentration of Nefazodone can be decreased when it is combined with Mitotane.
NelfinavirThe serum concentration of Nelfinavir can be decreased when it is combined with Mitotane.
NetupitantThe serum concentration of Netupitant can be decreased when it is combined with Mitotane.
NevirapineThe serum concentration of Nevirapine can be decreased when it is combined with Mitotane.
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Mitotane.
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Mitotane.
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Mitotane.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Mitotane.
NisoldipineThe serum concentration of Nisoldipine can be decreased when it is combined with Mitotane.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Mitotane.
OlaparibThe serum concentration of Olaparib can be decreased when it is combined with Mitotane.
OndansetronThe serum concentration of Ondansetron can be decreased when it is combined with Mitotane.
OspemifeneThe serum concentration of Ospemifene can be decreased when it is combined with Mitotane.
OxycodoneThe serum concentration of Oxycodone can be decreased when it is combined with Mitotane.
PaclitaxelThe serum concentration of Paclitaxel can be decreased when it is combined with Mitotane.
PalbociclibThe serum concentration of Palbociclib can be decreased when it is combined with Mitotane.
PanobinostatThe serum concentration of Panobinostat can be decreased when it is combined with Mitotane.
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Mitotane.
PerampanelThe serum concentration of Perampanel can be decreased when it is combined with Mitotane.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Mitotane.
PimozideThe serum concentration of Pimozide can be decreased when it is combined with Mitotane.
PipotiazineThe serum concentration of Pipotiazine can be decreased when it is combined with Mitotane.
PonatinibThe serum concentration of Ponatinib can be decreased when it is combined with Mitotane.
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Mitotane.
PrednisoloneThe serum concentration of Prednisolone can be decreased when it is combined with Mitotane.
PrednisoneThe serum concentration of Prednisone can be decreased when it is combined with Mitotane.
PrimaquineThe serum concentration of Primaquine can be decreased when it is combined with Mitotane.
ProgesteroneThe serum concentration of Progesterone can be decreased when it is combined with Mitotane.
PropafenoneThe serum concentration of Propafenone can be decreased when it is combined with Mitotane.
QuetiapineThe serum concentration of Quetiapine can be decreased when it is combined with Mitotane.
QuinidineThe serum concentration of Quinidine can be decreased when it is combined with Mitotane.
QuinineThe serum concentration of Quinine can be decreased when it is combined with Mitotane.
RabeprazoleThe serum concentration of Rabeprazole can be decreased when it is combined with Mitotane.
RanolazineThe serum concentration of Ranolazine can be decreased when it is combined with Mitotane.
RegorafenibThe serum concentration of Regorafenib can be decreased when it is combined with Mitotane.
RepaglinideThe serum concentration of Repaglinide can be decreased when it is combined with Mitotane.
Repository corticotropinThe serum concentration of Repository corticotropin can be decreased when it is combined with Mitotane.
RifabutinThe serum concentration of Rifabutin can be decreased when it is combined with Mitotane.
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Mitotane.
RiociguatThe serum concentration of Riociguat can be decreased when it is combined with Mitotane.
RitonavirThe serum concentration of Ritonavir can be decreased when it is combined with Mitotane.
RivaroxabanThe serum concentration of Rivaroxaban can be decreased when it is combined with Mitotane.
RoflumilastThe serum concentration of Roflumilast can be decreased when it is combined with Mitotane.
RolapitantThe serum concentration of Rolapitant can be decreased when it is combined with Mitotane.
RomidepsinThe serum concentration of Romidepsin can be decreased when it is combined with Mitotane.
RuxolitinibThe serum concentration of Ruxolitinib can be decreased when it is combined with Mitotane.
SaquinavirThe serum concentration of Saquinavir can be decreased when it is combined with Mitotane.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Mitotane.
SildenafilThe serum concentration of Sildenafil can be decreased when it is combined with Mitotane.
SilodosinThe serum concentration of Silodosin can be decreased when it is combined with Mitotane.
SimeprevirThe serum concentration of Simeprevir can be decreased when it is combined with Mitotane.
SimvastatinThe serum concentration of Simvastatin can be decreased when it is combined with Mitotane.
SirolimusThe serum concentration of Sirolimus can be decreased when it is combined with Mitotane.
SolifenacinThe serum concentration of Solifenacin can be decreased when it is combined with Mitotane.
SonidegibThe serum concentration of Sonidegib can be decreased when it is combined with Mitotane.
SorafenibThe serum concentration of Sorafenib can be decreased when it is combined with Mitotane.
SpiramycinThe serum concentration of Spiramycin can be decreased when it is combined with Mitotane.
SpironolactoneThe therapeutic efficacy of Mitotane can be decreased when used in combination with Spironolactone.
StiripentolThe serum concentration of Stiripentol can be decreased when it is combined with Mitotane.
SunitinibThe serum concentration of Sunitinib can be decreased when it is combined with Mitotane.
SuvorexantThe serum concentration of Suvorexant can be decreased when it is combined with Mitotane.
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Mitotane.
TadalafilThe serum concentration of Tadalafil can be decreased when it is combined with Mitotane.
TamoxifenThe serum concentration of Tamoxifen can be decreased when it is combined with Mitotane.
TamsulosinThe serum concentration of Tamsulosin can be decreased when it is combined with Mitotane.
TasimelteonThe serum concentration of Tasimelteon can be decreased when it is combined with Mitotane.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Mitotane.
TelithromycinThe serum concentration of Telithromycin can be decreased when it is combined with Mitotane.
TemsirolimusThe serum concentration of Temsirolimus can be decreased when it is combined with Mitotane.
TeniposideThe serum concentration of Teniposide can be decreased when it is combined with Mitotane.
TetracyclineThe serum concentration of Tetracycline can be decreased when it is combined with Mitotane.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Mitotane.
TiagabineThe serum concentration of Tiagabine can be decreased when it is combined with Mitotane.
TicagrelorThe serum concentration of the active metabolites of Ticagrelor can be reduced when Ticagrelor is used in combination with Mitotane resulting in a loss in efficacy.
TiclopidineThe serum concentration of Ticlopidine can be decreased when it is combined with Mitotane.
TipranavirThe serum concentration of Tipranavir can be decreased when it is combined with Mitotane.
TofacitinibThe serum concentration of Tofacitinib can be decreased when it is combined with Mitotane.
TolterodineThe serum concentration of Tolterodine can be decreased when it is combined with Mitotane.
TolvaptanThe serum concentration of Tolvaptan can be decreased when it is combined with Mitotane.
ToremifeneThe serum concentration of Toremifene can be decreased when it is combined with Mitotane.
TrabectedinThe serum concentration of Trabectedin can be decreased when it is combined with Mitotane.
TramadolThe serum concentration of Tramadol can be decreased when it is combined with Mitotane.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Mitotane.
TrazodoneThe serum concentration of Trazodone can be decreased when it is combined with Mitotane.
TriamcinoloneThe serum concentration of Triamcinolone can be decreased when it is combined with Mitotane.
TriazolamThe serum concentration of Triazolam can be decreased when it is combined with Mitotane.
TrimethoprimThe serum concentration of Trimethoprim can be decreased when it is combined with Mitotane.
TrimipramineThe serum concentration of Trimipramine can be decreased when it is combined with Mitotane.
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Mitotane.
VandetanibThe serum concentration of Vandetanib can be decreased when it is combined with Mitotane.
VemurafenibThe serum concentration of Vemurafenib can be decreased when it is combined with Mitotane.
VenlafaxineThe serum concentration of Venlafaxine can be decreased when it is combined with Mitotane.
VerapamilThe serum concentration of Verapamil can be decreased when it is combined with Mitotane.
VilazodoneThe serum concentration of Vilazodone can be decreased when it is combined with Mitotane.
VinblastineThe serum concentration of Vinblastine can be decreased when it is combined with Mitotane.
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Mitotane.
VinorelbineThe serum concentration of Vinorelbine can be decreased when it is combined with Mitotane.
VorapaxarThe serum concentration of Vorapaxar can be decreased when it is combined with Mitotane.
VortioxetineThe serum concentration of Vortioxetine can be decreased when it is combined with Mitotane.
ZaleplonThe serum concentration of Zaleplon can be decreased when it is combined with Mitotane.
ZolpidemThe serum concentration of Zolpidem can be decreased when it is combined with Mitotane.
ZonisamideThe serum concentration of Zonisamide can be decreased when it is combined with Mitotane.
ZopicloneThe serum concentration of Zopiclone can be decreased when it is combined with Mitotane.
ZuclopenthixolThe serum concentration of Zuclopenthixol can be decreased when it is combined with Mitotane.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inducer
General Function:
Steroid 11-beta-monooxygenase activity
Specific Function:
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochrome P450 XIB.
Gene Name:
CYP11B1
Uniprot ID:
P15538
Molecular Weight:
57572.44 Da
References
  1. Lindhe O, Skogseid B, Brandt I: Cytochrome P450-catalyzed binding of 3-methylsulfonyl-DDE and o,p'-DDD in human adrenal zona fasciculata/reticularis. J Clin Endocrinol Metab. 2002 Mar;87(3):1319-26. [PubMed:11889204 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
unknown
General Function:
Iron ion binding
Specific Function:
Participates in the synthesis of thyroid hormones. Essential for the synthesis of various steroid hormones, participates in the reduction of mitochondrial cytochrome P450 for steroidogenesis. Transfers electrons from adrenodoxin reductase to CYP11A1, a cytochrome P450 that catalyzes cholesterol side-chain cleavage.
Gene Name:
FDX1
Uniprot ID:
P10109
Molecular Weight:
19392.475 Da
References
  1. Kandul SV, Iatsyk MI, Kononenko VIa: [Comparative study of the effect of chloditan on the concentration of cytochrome P-450 and adrenodoxin in various organs of the dog and rat]. Fiziol Zh. 1986 Sep-Oct;32(5):579-84. [PubMed:3770229 ]
  2. Cabrini DA, Campos MM, Tratsk KS, Merino VF, Silva JA Jr, Souza GE, Avellar MC, Pesquero JB, Calixto JB: Molecular and pharmacological evidence for modulation of kinin B(1) receptor expression by endogenous glucocorticoids hormones in rats. Br J Pharmacol. 2001 Jan;132(2):567-77. [PubMed:11159707 ]
  3. Cai W, Counsell RE, Schteingart DE, Sinsheimer JE, Vaz AD, Wotring LL: Adrenal proteins bound by a reactive intermediate of mitotane. Cancer Chemother Pharmacol. 1997;39(6):537-40. [PubMed:9118466 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Androgen binding
Specific Function:
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
Gene Name:
SHBG
Uniprot ID:
P04278
Molecular Weight:
43778.755 Da
References
  1. Nader N, Raverot G, Emptoz-Bonneton A, Dechaud H, Bonnay M, Baudin E, Pugeat M: Mitotane has an estrogenic effect on sex hormone-binding globulin and corticosteroid-binding globulin in humans. J Clin Endocrinol Metab. 2006 Jun;91(6):2165-70. Epub 2006 Mar 21. [PubMed:16551731 ]
  2. van Seters AP, Moolenaar AJ: Mitotane increases the blood levels of hormone-binding proteins. Acta Endocrinol (Copenh). 1991 May;124(5):526-33. [PubMed:1903011 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Steroid binding
Specific Function:
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name:
SERPINA6
Uniprot ID:
P08185
Molecular Weight:
45140.49 Da
References
  1. Nader N, Raverot G, Emptoz-Bonneton A, Dechaud H, Bonnay M, Baudin E, Pugeat M: Mitotane has an estrogenic effect on sex hormone-binding globulin and corticosteroid-binding globulin in humans. J Clin Endocrinol Metab. 2006 Jun;91(6):2165-70. Epub 2006 Mar 21. [PubMed:16551731 ]
  2. Tron'ko MD: [Effect of chlodithane (o,p'-DDD) on transcortin binding ability in Itsenko-Cushing's disease]. Fiziol Zh. 1970 Nov-Dec;16(6):844-5. [PubMed:5520073 ]
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Drug created on June 13, 2005 07:24 / Updated on January 16, 2014 10:50