2-hydroxyflutamide (T3D4993)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationXML
Record Information
Version2.0
Creation Date2014-10-14 21:20:43 UTC
Update Date2014-12-24 20:27:01 UTC
Accession NumberT3D4993
Identification
Common Name2-hydroxyflutamide
ClassSmall Molecule
Description2-hydroxyflutamide is a metabolite of flutamide. Flutamide is an oral nonsteroidal antiandrogen drug primarily used to treat prostate cancer. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, it prevents them from stimulating the prostate cancer cells to grow. Flutamide has been largely replaced by a newer member of this class, bicalutamide, due to a better side-effect profile. (Wikipedia)
Compound Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
2-Hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide
2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
2-Hydroxy-flutamide
Hydroxyflutamide
Chemical FormulaC11H11F3N2O4
Average Molecular Mass292.211 g/mol
Monoisotopic Mass292.067 g/mol
CAS Registry Number52806-53-8
IUPAC Name2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanimidic acid
Traditional Namehydroxyflutamide
SMILESCC(C)(O)C(O)=NC1=CC(=C(C=C1)N(=O)=O)C(F)(F)F
InChI IdentifierInChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)
InChI KeyInChIKey=YPQLFJODEKMJEF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTrifluoromethylbenzenes
Direct ParentTrifluoromethylbenzenes
Alternative Parents
Substituents
  • Trifluoromethylbenzene
  • Nitrobenzene
  • Anilide
  • Nitroaromatic compound
  • N-arylamide
  • Tertiary alcohol
  • Carboxamide group
  • C-nitro compound
  • Secondary carboxylic acid amide
  • Organic nitro compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Hydrocarbon derivative
  • Alkyl halide
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organic oxygen compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Alkyl fluoride
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic zwitterion
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Kidney
  • Liver
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point125-130C
Boiling Point443.801 C at 760 mmHg
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP1.91ALOGPS
logP2.94ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)3.8ChemAxon
pKa (Strongest Basic)0.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area98.64 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity65.88 m³·mol⁻¹ChemAxon
Polarizability24.07 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9050000000-f84e588ae9034a41b2dc2017-09-20View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9611200000-62d9053b443fcb3656422017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-06g0-9800000000-18021dcb8f1e955f52ad2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a6r-6940000000-dd38c2394309e1626e1e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a6r-6940000000-81afeee01eada15bcf382021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-2490000000-6d0e498f9c29ac103dd72021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0090000000-1892a491307294bb679e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0090000000-73482035831e8bedb25c2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0090000000-e7bc28de00b2591fa92a2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-4c17b53efb57846397e42016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3090000000-d9e96ed3ee61c4eaf8ed2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9010000000-67e035c44d2e533ec7302016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c848958ccc3b75da2ac32016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1190000000-78cf87749f2c226b1da42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9i-9200000000-b8932182dc70103690522016-08-03View Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityHydroxyflutamide is an antiandrogen. Antiandrogens alter the androgen pathway by blocking the appropriate receptors, competing for binding sites on the cell's surface, or affecting androgen production. Antiandrogens are classified as steroidal or nonsteroidal. Steroidal antiandrogens not only counter androgens, but also affect secondary sex characteristics. Steroidal antiandrogens directly affect gene expression due to their fat-soluble nature that allows them to diffuse through the plasma membrane's phospholipid bilayer and prevent the binding of testosterone and dihydrotestosterone (DHT) to the androgen receptor. Inhibition of androgen production occurs through a unique mechanism for each antiandrogen. (Wikipedia)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIn men, antiandrogens are most frequently used to treat prostate cancer. In women, antiandrogens are used to decrease levels of male hormones causing symptoms of hyperandrogenism. (Wikipedia)
Minimum Risk LevelNot Available
Health EffectsEnvironmental antiandrogens can have harmful effects on reproductive organ development in fetuses exposed in utero as well as their offspring. (Wikipedia)
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB60949
PubChem Compound ID91649
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDC14204
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available