2-hydroxyflutamide (CHEM003947)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-10-14 21:20:43 UTC
Update Date2016-11-09 01:09:15 UTC
Accession NumberCHEM003947
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)
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Metabolite
  • Natural Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
OH-FlutamideHMDB
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 KeyYPQLFJODEKMJEF-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
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9050000000-f84e588ae9034a41b2dcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0089-9611200000-62d9053b443fcb365642Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-06g0-9800000000-18021dcb8f1e955f52adSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a6r-6940000000-dd38c2394309e1626e1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-0a6r-6940000000-81afeee01eada15bcf38Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-2490000000-6d0e498f9c29ac103dd7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0006-0090000000-1892a491307294bb679eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-0090000000-73482035831e8bedb25cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0090000000-e7bc28de00b2591fa92aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0090000000-4c17b53efb57846397e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3090000000-d9e96ed3ee61c4eaf8edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059f-9010000000-67e035c44d2e533ec730Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-c848958ccc3b75da2ac3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1190000000-78cf87749f2c226b1da4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9i-9200000000-b8932182dc7010369052Spectrum
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
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0060949
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkHydroxyflutamide
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID91649
Kegg Compound IDC14204
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available