Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:45:29 UTC
HMDB IDHMDB0014786
Secondary Accession Numbers
  • HMDB14786
Metabolite Identification
Common NameMitotane
DescriptionMitotane is only found in individuals that have used or taken this drug. It is 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]Its 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.
Structure
Data?1582753220
Synonyms
ValueSource
LysodrenKegg
Bristol myers squibb brand OF mitotaneMeSH, HMDB
KhloditanMeSH, HMDB
ortho,Para-DDDMeSH, HMDB
ChloditanMeSH, HMDB
Bristol-myers squibb brand OF mitotaneMeSH, HMDB
O,P-DDDMeSH, HMDB
ortho,Para DDDMeSH, HMDB
ChlodithaneMeSH, HMDB
MytotanMeSH, HMDB
Chemical FormulaC14H10Cl4
Average Molecular Weight320.041
Monoisotopic Molecular Weight317.953661148
IUPAC Name1-chloro-4-[2,2-dichloro-1-(2-chlorophenyl)ethyl]benzene
Traditional Namemitotane
CAS Registry Number53-19-0
SMILES
ClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl
InChI Identifier
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
InChI KeyJWBOIMRXGHLCPP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes 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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point77 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.4e-06 g/LNot Available
LogP6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.4e-06 g/LALOGPS
logP10(6.08) g/LALOGPS
logP10(6.11) g/LChemAxon
logS10(-7.5) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.97 m³·mol⁻¹ChemAxon
Polarizability29.93 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MitotaneClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl3241.8Standard polar33892256
MitotaneClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl2129.3Standard non polar33892256
MitotaneClC(Cl)C(C1=CC=C(Cl)C=C1)C1=CC=CC=C1Cl2182.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Mitotane GC-EI-Q (Non-derivatized)splash10-000i-2590000000-2d3f8090ffa4733bf9ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mitotane GC-EI-Q (Non-derivatized)splash10-000i-2590000000-2d3f8090ffa4733bf9ee2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mitotane GC-MS (Non-derivatized) - 70eV, Positivesplash10-0019-3190000000-3e8980db36b0ac7be7c92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mitotane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mitotane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-2690000000-770065ddc57899130a312014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 10V, Positive-QTOFsplash10-014i-0029000000-a8fe8b7a30127f18cfcf2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 20V, Positive-QTOFsplash10-014i-0029000000-b5f28037c9691eb240472016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 40V, Positive-QTOFsplash10-0ac0-0790000000-fe84d84c9218b81962922016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 10V, Negative-QTOFsplash10-014i-0009000000-eddb407ee0b99900a0ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 20V, Negative-QTOFsplash10-014i-0229000000-967d4bba6420d7542b782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 40V, Negative-QTOFsplash10-01q9-0390000000-de32116845b75e0077f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 10V, Positive-QTOFsplash10-014i-0039000000-3c403b01150c1ceb18132021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 20V, Positive-QTOFsplash10-001i-0091000000-a71d76ec2ab1019a49272021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 40V, Positive-QTOFsplash10-000i-0290000000-251e3f81d8a1025f44362021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 10V, Negative-QTOFsplash10-014i-0039000000-90d3b740113c4fec06c32021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 20V, Negative-QTOFsplash10-0159-1096000000-d8dfb53c7c6dd6d1051a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mitotane 40V, Negative-QTOFsplash10-001i-9160000000-978ead17186c9fd3851c2021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00648 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00648 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00648
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4066
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMitotane
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1150611
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in 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
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 ]
General function:
Energy production and conversion
Specific function:
Participates in the synthesis of thyroid hormones. Transfers electrons from adrenodoxin reductase to the cholesterol side chain cleavage cytochrome P450
Gene Name:
FDX1
Uniprot ID:
P10109
Molecular weight:
19393.0
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 ]