Trilostane (CHEM016922)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:47:39 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016922
Identification
Common NameTrilostane
ClassSmall Molecule
DescriptionTrilostane is an inhibitor of 3 beta-hydroxysteroid dehydrogenase used in the treatment of Cushing's syndrome. It was withdrawn from the United States market in April 1994.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TrilostanoChEBI
TrilostanumChEBI
DesopanKegg
ModrenalKegg
4alpha,5-Epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrileHMDB
Chemical FormulaC20H27NO3
Average Molecular Mass329.433 g/mol
Monoisotopic Mass329.199 g/mol
CAS Registry Number13647-35-3
IUPAC Name(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.0²,⁸.0⁶,⁸.0¹²,¹⁶]octadec-4-ene-4-carbonitrile
Traditional Nametrilostane
SMILES[H][C@]12O[C@]11CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]1(C)CC(C#N)=C2O
InChI IdentifierInChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
InChI KeyKVJXBPDAXMEYOA-CXANFOAXSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • Estrane-skeleton
  • Cyclic alcohol
  • Secondary alcohol
  • Dialkyl ether
  • Enol
  • Oxirane
  • Ether
  • Carbonitrile
  • Nitrile
  • Organoheterocyclic compound
  • Oxacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP2.41ALOGPS
logP2.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)5.23ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area76.78 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.17 m³·mol⁻¹ChemAxon
Polarizability36.96 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ik9-3697000000-af2f49f13d139eac8699Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0adi-4074900000-0871d982b0c9c78ee04bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-002f-9075000000-1da8d2bce11b199e6ae7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-000x-8490000000-5c94811dae50400973f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-004i-1009000000-3c90bf59829f923f3ecbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-004i-0009000000-06fd800fcd666ed6b409Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014i-0930000000-724aa1c092e58c7c72c1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-0006-4950000000-252ada46341ba1485344Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0udi-0092000000-03cdb20a05a4dd66ccd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-001i-0009000000-5008f2d6d59863b60347Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00r7-0191000000-66f49b3ef9aaa33ee43bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-014i-0590000000-4fa0eb545e6d0b7ed6d9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00r7-0191000000-a97ac92908c84413eb43Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-01b9-4920000000-feacd7efa065a9b6bfcfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-01dl-5950000000-7b266af2b926fe90bbcdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014i-0930000000-0e6461981c695c95e322Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-0019000000-8b1592dcd1075be8e6c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-0289000000-5aba04fec65a6b4e7e80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9230000000-a7730c61179e8cf71251Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-2793c8c4f9445fececbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0029000000-98f981d26f779dc0bd6dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0292-5193000000-a1e424641cac8997b54bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-ae1c08c80815d3354b58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a59-3986000000-143177beea0b413dd522Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-5955000000-c4f6dc5057a30e34a5deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0009000000-93fb7ff56b0b7a4bf0f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0009000000-2b46248186d5598f4196Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01108
HMDB IDHMDB0015240
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrilostane
Chemspider ID570949
ChEBI ID32260
PubChem Compound ID656583
Kegg Compound IDC12580
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Komanicky P, Spark RF, Melby JC: Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis. J Clin Endocrinol Metab. 1978 Nov;47(5):1042-51.
2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
6. The lipid handbook with CD-ROM