ContaminantDB: Flutamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2014-09-11 05:15:47 UTC

Update Date

2016-11-09 01:09:12 UTC

Accession Number

CHEM003725

Identification

Common Name

Flutamide

Class

Small Molecule

Description

An 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4'-Nitro-3'-trifluoromethylisobutyranilide	ChEBI
alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide	ChEBI
Eulexin	ChEBI
Flutamida	ChEBI
Flutamidum	ChEBI
Niftolid	ChEBI
Niftolide	ChEBI
a,a,a-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide	Generator
Α,α,α-trifluoro-2-methyl-4'-nitro-m-propionotoluidide	Generator
Flutamide usp25	HMDB
Euflex	HMDB
Eulexine	HMDB
Fluken	HMDB
Flulem	HMDB
Fluta cell	HMDB
Fluta-gry	HMDB
Flutaplex	HMDB
Fugerel	HMDB
Juta brand OF flutamide	HMDB
Novo flutamide	HMDB
PMS-Flutamide	HMDB
Pharmascience brand OF flutamide	HMDB
Prasfarma brand OF flutamide	HMDB
Prostica	HMDB
Schering brand OF flutamide	HMDB
Schering-plough brand OF flutamide	HMDB
TAD brand OF flutamide	HMDB
Cell pharm brand OF flutamide	HMDB
1a Brand OF flutamide	HMDB
Apo flutamide	HMDB
Apogepha brand OF flutamide	HMDB
Chimax	HMDB
Cytamid	HMDB
Fluta gry	HMDB
Fluta-cell	HMDB
Flutacell	HMDB
Grisetin	HMDB
Gry brand OF flutamide	HMDB
Lemery brand OF flutamide	HMDB
Q Pharm brand OF flutamide	HMDB
Apo-flutamide	HMDB
Ciclum brand OF flutamide	HMDB
Drogenil	HMDB
Flumid	HMDB
FlutaGRY	HMDB
Flutexin	HMDB
Inibsa brand OF flutamide	HMDB
Ipsen brand OF flutamide	HMDB
PMS Flutamide	HMDB
Prostacur	HMDB
Prostogenat	HMDB
Testotard	HMDB
Esparma brand OF flutamide	HMDB
Alphapharm brand OF flutamide	HMDB
Apimid	HMDB
ApoFlutamide	HMDB
Apotex brand OF flutamide	HMDB
Azupharma brand OF flutamide	HMDB
Chephasaar brand OF flutamide	HMDB
Chiron brand OF flutamide	HMDB
Essex brand OF flutamide	HMDB
Fluta 1a pharma	HMDB
Flutamin	HMDB
Flutandrona	HMDB
Hexal brand OF flutamide	HMDB
Kendrick brand OF flutamide	HMDB
Novo-flutamide	HMDB
NovoFlutamide	HMDB
Novopharm brand OF flutamide	HMDB
Oncosal	HMDB
Q-Pharm brand OF flutamide	HMDB
Schering plough brand OF flutamide	HMDB
Tedec meiji brand OF flutamide	HMDB

Chemical Formula

C₁₁H₁₁F₃N₂O₃

Average Molecular Mass

276.212 g/mol

Monoisotopic Mass

276.072 g/mol

CAS Registry Number

13311-84-7

IUPAC Name

2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide

Traditional Name

flutamide

SMILES

CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

InChI Identifier

InChI=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 Key

MKXKFYHWDHIYRV-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Trifluoromethylbenzenes

Direct Parent

Trifluoromethylbenzenes

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:5132 )
(trifluoromethyl)benzenes (CHEBI:5132 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	111.5-112.5°C
Boiling Point	Not Available
Solubility	9.45 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.0057 g/L	ALOGPS
logP	2.55	ALOGPS
logP	3.27	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	63.42 m³·mol⁻¹	ChemAxon
Polarizability	23.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9280000000-95879ab49ae3474dd134	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0290000000-cca4c08f2a9bb3fc6f57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-004i-0190000000-df05faf7e38e6d6da203	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000i-3900000000-8b7e5888950eed07b29b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-004i-0090000000-983edf51e9c479db69a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0190000000-df05faf7e38e6d6da203	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0290000000-cca4c08f2a9bb3fc6f57	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-03di-2940000000-170008eb50a63f0664d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-0gx0-1900000000-c322f29e305a6d10044c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0940000000-8c0e8ce0c0167f824210	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-3ec575077e4f9903d0af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-0940000000-5a90366233a810251923	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0udi-0390000000-bb6d9f3ab642b5c061ba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090000000-cdcab2cffbd217c82fad	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0920000000-3d0edd4f5b6b7545a7f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-0udi-0890000000-9c05c9f4c668a596f70e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0910000000-abf238316a2db628c154	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0920000000-9eb906d56b8ae34b4681	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-0il0-0920000000-a14d1afe6adfae49f6ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-0ufr-0190000000-0c4cfbc09b7620965ab5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-7122c7547dc4f518e9fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-8090000000-02b603738815e91326c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-9010000000-19ee080aa7e8861af1ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-e5a1eaa719d4f63bf6f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2090000000-13768fb84641e8448d75	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0076-9000000000-10b226e4bd1f69316fa1	Spectrum

Toxicity Profile

Route of Exposure

Rapidly and completely absorbed.

Mechanism of Toxicity

Flutamide 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.

Metabolism

Flutamide 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 Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

In animal studies with flutamide alone, signs of overdose included hypoactivity, piloerection, slow respiration, ataxia, and/or lacrimation, anorexia, tranquilization, emesis, and methemoglobinemia.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00499

HMDB ID

HMDB0014642

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Link

General References

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

Flutamide (CHEM003725)

Structure for CHEM003725: Flutamide