Identification

Name
Flutamide
Accession Number
DB00499  (APRD00984)
Type
Small Molecule
Groups
Approved
Description

An antiandrogen with about the same potency as cyproterone in rodent and canine species.

Structure
Thumb
Synonyms
  • 4'-Nitro-3'-trifluoromethylisobutyranilide
  • alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidide
  • Flutamid
  • Flutamida
  • Flutamide
  • Flutamidum
  • FTA
  • NFBA
  • Niftolid
  • Niftolide
External IDs
Sch 13521 / SCH-13521
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-flutamideTablet250 mgOralDominion PharmacalNot applicableNot applicableCanada
EuflexTablet250 mgOralMerck Ltd.1984-12-312015-06-01Canada
FlutamideTablet250 mgOralPharmel Inc1998-12-012016-10-25Canada
FlutamideTablet250 mgOralSchering Plough1996-12-312014-07-31Canada
FlutamideTablet250 mgOralPharmascience Inc1997-10-312016-10-28Canada
Flutamide-250Tablet250 mgOralPro Doc Limitee1999-02-222009-07-23Canada
Nu-flutamide TabletsTablet250 mgOralNu Pharm IncNot applicableNot applicableCanada
Penta-flutamideTablet250 mgOralPentapharm Ltd.Not applicableNot applicableCanada
PMS-flutamideTablet250 mgOralPharmascience Inc1997-02-21Not applicableCanada
Teva-flutamideTablet250 mgOralTeva1997-01-16Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-flutamideTablet250 mgOralApotex Corporation1998-10-08Not applicableCanada
FlutamideCapsule125 mg/1OralGolden State Medical Supply2001-09-18Not applicableUs
FlutamideCapsule125 mg/1OralTeva2001-09-192018-05-31Us00172 4960 58 nlmimage10 af2dd78e
FlutamideCapsule125 mg/1OralActavis Pharma Company2011-07-28Not applicableUs
FlutamideCapsule125 mg/1OralCipla Limited2016-09-21Not applicableUs
FlutamideCapsule125 mg/1OralPar Pharmaceutical2001-09-18Not applicableUs
International/Other Brands
Andraxan (CSC) / Antipros (Medicamerc) / Curestat (Advanced Pharmaceutical) / Cytomid (Cipla) / Dedile (Ivax) / Drogenil (Bayer) / Elbat (Genepharm) / Etaconil (Nolver) / Eulexin (Schering-Plough) / Farostat (Orion) / Flimutal (Cryopharma) / Flucinom (Merck Sharp & Dohme) / Flulem (Teva) / Odyne (Nippon Kayaku) / Prostadirex (Sanofi-Aventis) / Prostanon (Pharmachemie)
Categories
UNII
76W6J0943E
CAS number
13311-84-7
Weight
Average: 276.2118
Monoisotopic: 276.072176843
Chemical Formula
C11H11F3N2O3
InChI Key
MKXKFYHWDHIYRV-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
SMILES
CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

Pharmacology

Indication

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

Structured Indications
Pharmacodynamics

Flutamide is a nonsteroidal antiandrogen. In animal studies, flutamide demonstrates potent antiandrogenic effects. It exerts its antiandrogenic action by inhibiting androgen uptake and/or by inhibiting nuclear binding of androgen in target tissues or both. Prostatic carcinoma is known to be androgen-sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen, e.g. castration. Elevations of plasma testosterone and estradiol levels have been noted following flutamide administration.

Mechanism of action

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.

TargetActionsOrganism
AAndrogen receptor
antagonist
Human
UAryl hydrocarbon receptor
agonist
Human
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
Absorption

Rapidly and completely absorbed.

Volume of distribution
Not Available
Protein binding

94-96%

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.

Clearance
Not Available
Toxicity

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

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Flutamide can be increased when it is combined with Abiraterone.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Flutamide.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Flutamide.Experimental
AmiodaroneThe metabolism of Flutamide can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Flutamide can be increased when it is combined with Aprepitant.Approved, Investigational
ArmodafinilThe metabolism of Flutamide can be decreased when combined with Armodafinil.Approved, Investigational
AtazanavirThe metabolism of Flutamide can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Flutamide can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Flutamide can be decreased when combined with Azithromycin.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Flutamide.Approved, Investigational
BoceprevirThe metabolism of Flutamide can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Flutamide can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Flutamide can be decreased when it is combined with Bosentan.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Flutamide.Approved
CaffeineThe metabolism of Flutamide can be decreased when combined with Caffeine.Approved
Capromab pendetideFlutamide may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CarbamazepineThe metabolism of Flutamide can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Flutamide can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Flutamide can be decreased when combined with Chloramphenicol.Approved, Vet Approved
CholecalciferolThe metabolism of Flutamide can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Flutamide.Approved, Investigational
CimetidineThe metabolism of Flutamide can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Flutamide can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Flutamide can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Flutamide can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Flutamide can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Flutamide can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Flutamide can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Flutamide can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Flutamide.Approved, Investigational
CyclosporineThe metabolism of Flutamide can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Flutamide.Experimental
Cyproterone acetateThe serum concentration of Flutamide can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Flutamide can be decreased when it is combined with Dabrafenib.Approved
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Flutamide.Approved, Investigational
DarunavirThe metabolism of Flutamide can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Flutamide can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Flutamide can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Flutamide can be decreased when combined with Delavirdine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Flutamide.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Flutamide.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Flutamide.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Flutamide.Approved
DihydroergotamineThe metabolism of Flutamide can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Flutamide can be decreased when combined with Diltiazem.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Flutamide.Approved, Investigational
DosulepinThe metabolism of Flutamide can be decreased when combined with Dosulepin.Approved
DoxycyclineThe metabolism of Flutamide can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Flutamide can be decreased when combined with Dronedarone.Approved
EfavirenzThe metabolism of Flutamide can be decreased when combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Flutamide can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Flutamide can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe metabolism of Flutamide can be decreased when combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Flutamide can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe metabolism of Flutamide can be decreased when combined with Etravirine.Approved
FluconazoleThe metabolism of Flutamide can be decreased when combined with Fluconazole.Approved
FluoxetineThe metabolism of Flutamide can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvoxamineThe metabolism of Flutamide can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Flutamide can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Flutamide can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Flutamide can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Flutamide can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Flutamide can be decreased when combined with Gemfibrozil.Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Flutamide.Experimental
IdelalisibThe serum concentration of Flutamide can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Flutamide can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Flutamide can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Flutamide can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Flutamide can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Flutamide can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Flutamide can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Flutamide can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Flutamide can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Flutamide.Experimental
LidocaineThe metabolism of Flutamide can be decreased when combined with Lidocaine.Approved, Vet Approved
LobeglitazoneThe metabolism of Flutamide can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Flutamide can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Flutamide can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Flutamide can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Flutamide can be decreased when it is combined with Lumacaftor.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Flutamide.Experimental
MexiletineThe metabolism of Flutamide can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Flutamide can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Flutamide can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Flutamide can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Flutamide can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Flutamide can be decreased when combined with Modafinil.Approved, Investigational
NefazodoneThe metabolism of Flutamide can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Flutamide can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Flutamide can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Flutamide can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Flutamide can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Flutamide can be decreased when combined with Nilotinib.Approved, Investigational
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Flutamide.Approved
OlaparibThe metabolism of Flutamide can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Flutamide.Experimental, Investigational
OmeprazoleThe metabolism of Flutamide can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Flutamide can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Flutamide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Flutamide.Approved, Vet Approved
PalbociclibThe serum concentration of Flutamide can be increased when it is combined with Palbociclib.Approved
PantoprazoleThe metabolism of Flutamide can be decreased when combined with Pantoprazole.Approved
Peginterferon alfa-2bThe serum concentration of Flutamide can be increased when it is combined with Peginterferon alfa-2b.Approved
PentobarbitalThe metabolism of Flutamide can be increased when combined with Pentobarbital.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Flutamide.Experimental
PhenobarbitalThe metabolism of Flutamide can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Flutamide can be increased when combined with Phenytoin.Approved, Vet Approved
PosaconazoleThe metabolism of Flutamide can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrilocaineThe risk or severity of adverse effects can be increased when Flutamide is combined with Prilocaine.Approved
PrimidoneThe metabolism of Flutamide can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Flutamide.Experimental
RanolazineThe metabolism of Flutamide can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Flutamide can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Flutamide can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Flutamide can be increased when combined with Rifapentine.Approved
RopiniroleThe metabolism of Flutamide can be decreased when combined with Ropinirole.Approved, Investigational
SaquinavirThe metabolism of Flutamide can be decreased when combined with Saquinavir.Approved, Investigational
SertralineThe metabolism of Flutamide can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Flutamide can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Flutamide can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Flutamide can be increased when it is combined with Simeprevir.Approved
Sodium NitriteThe risk or severity of adverse effects can be increased when Flutamide is combined with Sodium Nitrite.Approved
St. John's WortThe serum concentration of Flutamide can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Flutamide can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Flutamide can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Flutamide can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Flutamide can be decreased when combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Flutamide can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Flutamide can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Flutamide can be decreased when combined with Theophylline.Approved
TiclopidineThe metabolism of Flutamide can be decreased when combined with Ticlopidine.Approved
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Flutamide.Approved
TocilizumabThe serum concentration of Flutamide can be decreased when it is combined with Tocilizumab.Approved
TopiramateThe metabolism of Flutamide can be decreased when combined with Topiramate.Approved
TranylcypromineThe metabolism of Flutamide can be decreased when combined with Tranylcypromine.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Flutamide.Approved, Investigational
VemurafenibThe serum concentration of Flutamide can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Flutamide can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Flutamide can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Flutamide can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Flutamide can be decreased when combined with Ziprasidone.Approved
ZucapsaicinThe metabolism of Flutamide can be decreased when combined with Zucapsaicin.Approved
Food Interactions
  • Take without regard to meals.

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.

US6228401
General References
  1. Link [Link]
External Links
Human Metabolome Database
HMDB14642
KEGG Drug
D00586
KEGG Compound
C07653
PubChem Compound
3397
PubChem Substance
46508874
ChemSpider
3280
BindingDB
50131270
ChEBI
5132
ChEMBL
CHEMBL806
Therapeutic Targets Database
DAP000301
PharmGKB
PA449685
HET
HFT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Flutamide
ATC Codes
L02BB01 — Flutamide
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
FDA label
Download (413 KB)
MSDS
Download (55.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCongenital Adrenal Hyperplasia (CAH) / Growth Disorders1
1CompletedTreatmentProstate Cancer2
1RecruitingOtherPolycystic Ovaries Syndrome1
1TerminatedTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer1
2Active Not RecruitingTreatmentProstate Cancer1
2CompletedPreventionCancer, Ovarian1
2CompletedPreventionProstate Cancer1
2CompletedTreatmentProstate Cancer5
2CompletedTreatmentProstate Cancer / Sexual Dysfunction and Infertility1
2CompletedTreatmentProstatic Neoplasms1
2RecruitingTreatmentPolycystic Ovary Syndrome (PCOS)1
2RecruitingTreatmentProstate Cancer1
2Unknown StatusTreatmentProstate Cancer2
2WithdrawnTreatmentAdenocarcinoma of the Prostate / Recurrent Prostate Cancer / Stage III Prostate Cancer / Stage IV Prostate Cancer1
2, 3RecruitingTreatmentStage I Prostate Adenocarcinoma / Stage II Prostate Adenocarcinoma / Stage III Prostate Adenocarcinoma1
3Active Not RecruitingTreatmentProstate Cancer5
3CompletedTreatmentAdenocarcinoma, Prostate1
3CompletedTreatmentProstate Cancer12
3CompletedTreatmentProstatic Neoplasms, Locally Advanced1
3TerminatedTreatmentProstate Cancer2
3Unknown StatusTreatmentProstate Cancer3
4CompletedTreatmentPremenstrual Syndrome1
4RecruitingTreatmentProstate Cancer1
Not AvailableActive Not RecruitingBasic ScienceHyperandrogenism / Polycystic Ovaries Syndrome1
Not AvailableCompletedNot AvailableMetabolic Syndromes / Polycystic Ovaries Syndrome1
Not AvailableRecruitingTreatmentCastration-Resistant Prostate Cancer (CRPC)1
Not AvailableTerminatedHealth Services ResearchPolycystic Ovaries Syndrome1

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Par pharmaceutical inc
  • Sandoz inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral125 mg/1
TabletOral250 mg
Prices
Unit descriptionCostUnit
Flutamide 125 mg capsule2.12USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)111.5-112.5Gold, E.H.; U.S. Patent 3,847,988; November 12, 1974; assigned to Schering Corp.
water solubility9.45 mg/LNot Available
logP3.35MORRIS,JJ ET AL. (1991)
Predicted Properties
PropertyValueSource
Water Solubility0.00566 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.42 m3·mol-1ChemAxon
Polarizability23.2 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9655
Caco-2 permeable+0.7533
P-glycoprotein substrateNon-substrate0.8131
P-glycoprotein inhibitor INon-inhibitor0.8254
P-glycoprotein inhibitor IINon-inhibitor0.9428
Renal organic cation transporterNon-inhibitor0.9535
CYP450 2C9 substrateNon-substrate0.7927
CYP450 2D6 substrateNon-substrate0.8935
CYP450 3A4 substrateSubstrate0.568
CYP450 1A2 substrateInhibitor0.9108
CYP450 2C9 inhibitorNon-inhibitor0.6306
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.5924
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6574
Ames testNon AMES toxic0.5728
CarcinogenicityCarcinogens 0.6077
BiodegradationNot ready biodegradable0.9924
Rat acute toxicity2.5770 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9881
hERG inhibition (predictor II)Non-inhibitor0.8734
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0090000000-983edf51e9c479db69a5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0190000000-df05faf7e38e6d6da203
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0290000000-cca4c08f2a9bb3fc6f57
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2940000000-170008eb50a63f0664d0

Taxonomy

Description
This compound 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
Nitrobenzenes / Anilides / Nitroaromatic compounds / N-arylamides / Secondary carboxylic acid amides / Propargyl-type 1,3-dipolar organic compounds / Organic oxoazanium compounds / Organopnictogen compounds / Organofluorides / Organic zwitterions
show 4 more
Substituents
Trifluoromethylbenzene / Nitrobenzene / Anilide / N-arylamide / Nitroaromatic compound / Carboxamide group / C-nitro compound / Organic nitro compound / Secondary carboxylic acid amide / Carboxylic acid derivative
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid amide, (trifluoromethyl)benzenes (CHEBI:5132)

Targets

Details
1. Androgen receptor
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Chang HC, Miyamoto H, Marwah P, Lardy H, Yeh S, Huang KE, Chang C: Suppression of Delta(5)-androstenediol-induced androgen receptor transactivation by selective steroids in human prostate cancer cells. Proc Natl Acad Sci U S A. 1999 Sep 28;96(20):11173-7. [PubMed:10500149]
  2. Martelli A, Campart GB, Carrozzino R, Ghia M, Mattioli F, Mereto E, Orsi P, Puglia CP: Evaluation of flutamide genotoxicity in rats and in primary human hepatocytes. Pharmacol Toxicol. 2000 Mar;86(3):129-34. [PubMed:10752671]
  3. Montalvo L, Carmena MJ, Solano RM, Clemente C, Roman ID, Sanchez-Chapado M, Prieto JC: Effect of flutamide-induced androgen-receptor blockade on adenylate cyclase activation through G-protein coupled receptors in rat prostate. Cell Signal. 2000 May;12(5):311-6. [PubMed:10822172]
  4. Pazos F, Sanchez-Franco F, Balsa JA, Escalada J, Palacios N, Cacicedo L: Mechanisms of reduced body growth in the pubertal feminized male rat: unbalanced estrogen and androgen action on the somatotropic axis. Pediatr Res. 2000 Jul;48(1):96-103. [PubMed:10879806]
  5. Shilling AD, Williams DE: The non-aromatizable androgen, dihydrotestosterone, induces antiestrogenic responses in the rainbow trout. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):187-94. [PubMed:11162924]
  6. Balk SP: Androgen receptor as a target in androgen-independent prostate cancer. Urology. 2002 Sep;60(3 Suppl 1):132-8; discussion 138-9. [PubMed:12231070]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Transcription regulatory region dna binding
Specific Function
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes...
Gene Name
AHR
Uniprot ID
P35869
Uniprot Name
Aryl hydrocarbon receptor
Molecular Weight
96146.705 Da
References
  1. Hu W, Sorrentino C, Denison MS, Kolaja K, Fielden MR: Induction of cyp1a1 is a nonspecific biomarker of aryl hydrocarbon receptor activation: results of large scale screening of pharmaceuticals and toxicants in vivo and in vitro. Mol Pharmacol. 2007 Jun;71(6):1475-86. Epub 2007 Feb 27. [PubMed:17327465]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Harmsen S, Meijerman I, Beijnen JH, Schellens JH: Nuclear receptor mediated induction of cytochrome P450 3A4 by anticancer drugs: a key role for the pregnane X receptor. Cancer Chemother Pharmacol. 2009 Jun;64(1):35-43. doi: 10.1007/s00280-008-0842-3. Epub 2008 Oct 7. [PubMed:18839173]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Wang B, Zhou SF: Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218. [PubMed:19754423]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. Shet MS, McPhaul M, Fisher CW, Stallings NR, Estabrook RW: Metabolism of the antiandrogenic drug (Flutamide) by human CYP1A2. Drug Metab Dispos. 1997 Nov;25(11):1298-303. [PubMed:9351907]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33