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Record Information
Version1.0
Creation Date2014-09-11 05:15:47 UTC
Update Date2016-11-09 01:09:12 UTC
Accession NumberCHEM003725
Identification
Common NameFlutamide
ClassSmall Molecule
DescriptionAn antiandrogen with about the same potency as cyproterone in rodent and canine species.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Androgen Antagonist
  • Antineoplastic Agent, Hormonal
  • Drug
  • Metabolite
  • Organic Compound
  • Organofluoride
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
4'-Nitro-3'-trifluoromethylisobutyranilideChEBI
alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidideChEBI
EulexinChEBI
FlutamidaChEBI
FlutamidumChEBI
NiftolidChEBI
NiftolideChEBI
a,a,a-Trifluoro-2-methyl-4'-nitro-m-propionotoluidideGenerator
Α,α,α-trifluoro-2-methyl-4'-nitro-m-propionotoluidideGenerator
Flutamide usp25HMDB
EuflexHMDB
EulexineHMDB
FlukenHMDB
FlulemHMDB
Fluta cellHMDB
Fluta-gryHMDB
FlutaplexHMDB
FugerelHMDB
Juta brand OF flutamideHMDB
Novo flutamideHMDB
PMS-FlutamideHMDB
Pharmascience brand OF flutamideHMDB
Prasfarma brand OF flutamideHMDB
ProsticaHMDB
Schering brand OF flutamideHMDB
Schering-plough brand OF flutamideHMDB
TAD brand OF flutamideHMDB
Cell pharm brand OF flutamideHMDB
1a Brand OF flutamideHMDB
Apo flutamideHMDB
Apogepha brand OF flutamideHMDB
ChimaxHMDB
CytamidHMDB
Fluta gryHMDB
Fluta-cellHMDB
FlutacellHMDB
GrisetinHMDB
Gry brand OF flutamideHMDB
Lemery brand OF flutamideHMDB
Q Pharm brand OF flutamideHMDB
Apo-flutamideHMDB
Ciclum brand OF flutamideHMDB
DrogenilHMDB
FlumidHMDB
FlutaGRYHMDB
FlutexinHMDB
Inibsa brand OF flutamideHMDB
Ipsen brand OF flutamideHMDB
PMS FlutamideHMDB
ProstacurHMDB
ProstogenatHMDB
TestotardHMDB
Esparma brand OF flutamideHMDB
Alphapharm brand OF flutamideHMDB
ApimidHMDB
ApoFlutamideHMDB
Apotex brand OF flutamideHMDB
Azupharma brand OF flutamideHMDB
Chephasaar brand OF flutamideHMDB
Chiron brand OF flutamideHMDB
Essex brand OF flutamideHMDB
Fluta 1a pharmaHMDB
FlutaminHMDB
FlutandronaHMDB
Hexal brand OF flutamideHMDB
Kendrick brand OF flutamideHMDB
Novo-flutamideHMDB
NovoFlutamideHMDB
Novopharm brand OF flutamideHMDB
OncosalHMDB
Q-Pharm brand OF flutamideHMDB
Schering plough brand OF flutamideHMDB
Tedec meiji brand OF flutamideHMDB
Chemical FormulaC11H11F3N2O3
Average Molecular Mass276.212 g/mol
Monoisotopic Mass276.072 g/mol
CAS Registry Number13311-84-7
IUPAC Name2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Traditional Nameflutamide
SMILESCC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F
InChI IdentifierInChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
InChI KeyMKXKFYHWDHIYRV-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
  • N-arylamide
  • Nitroaromatic compound
  • Carboxamide group
  • C-nitro compound
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Alkyl halide
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organic oxygen compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alkyl fluoride
  • Organic zwitterion
  • Carbonyl group
  • 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 LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point111.5-112.5°C
Boiling PointNot Available
Solubility9.45 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP2.55ALOGPS
logP3.27ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.17ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.42 m³·mol⁻¹ChemAxon
Polarizability23.2 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0a4l-9280000000-95879ab49ae3474dd134View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0290000000-cca4c08f2a9bb3fc6f57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-004i-0190000000-df05faf7e38e6d6da203View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-000i-3900000000-8b7e5888950eed07b29bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-0090000000-983edf51e9c479db69a5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0190000000-df05faf7e38e6d6da203View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0290000000-cca4c08f2a9bb3fc6f57View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-2940000000-170008eb50a63f0664d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-7122c7547dc4f518e9faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-8090000000-02b603738815e91326c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9010000000-19ee080aa7e8861af1ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-e5a1eaa719d4f63bf6f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2090000000-13768fb84641e8448d75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0076-9000000000-10b226e4bd1f69316fa1View in MoNA
Toxicity Profile
Route of ExposureRapidly and completely absorbed.
Mechanism of ToxicityFlutamide is a nonsteroidal antiandrogen that blocks the action of both endogenous and exogenous testosterone by binding to the androgen receptor. In addition Flutamide is a potent inhibitor of testosterone-stimulated prostatic DNA synthesis. Moreover, it is capable of inhibiting prostatic nuclear uptake of androgen.
MetabolismFlutamide is rapidly and extensively metabolized, with flutamide comprising only 2.5% of plasma radioactivity 1 hour after administration. Route of Elimination: Flutamide and its metabolites are excreted mainly in the urine with only 4.2% of a single dose excreted in the feces over 72 hours. Half Life: The plasma half-life for the alpha-hydroxylated metabolite of flutamide (an active metabolite) is approximately 6 hours.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsIn animal studies with flutamide alone, signs of overdose included hypoactivity, piloerection, slow respiration, ataxia, and/or lacrimation, anorexia, tranquilization, emesis, and methemoglobinemia.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00499
HMDB IDHMDB0014642
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFlutamide
Chemspider ID3280
ChEBI ID5132
PubChem Compound ID3397
Kegg Compound IDC07653
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Jack Lawrence James, Louis Frank Molnar, Jr., Tania E. Toney-Parker, “Processes for preparing flutamide compounds and compounds prepared by such processes.” U.S. Patent US 6,228,401, issued November, 1976.

MSDSLink
General References
1. BC Cancer Agency: http://www.bccancer.bc.ca/HPI/DrugDatabase/DrugIndexPro/Flutamide.htm