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Identification
NameFlutamide
Accession NumberDB00499  (APRD00984)
TypeSmall Molecule
GroupsApproved
DescriptionAn 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
Eulexin
Flutamid
Flutamida
Flutamide
Flutamidum
FTA
NFBA
Niftolid
Niftolide
External Identifiers
  • Sch 13521
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dom-flutamideTablet250 mgOralDominion PharmacalNot applicableNot applicableCanada
EuflexTablet250 mgOralMerck Canada Inc1984-12-312015-06-01Canada
FlutamideTablet250 mgOralPharmascience Inc1997-10-312016-10-28Canada
FlutamideTablet250 mgOralPharmel Inc1998-12-012016-10-25Canada
FlutamideTablet250 mgOralSchering Plough Canada Inc1996-12-312014-07-31Canada
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 mgOralTeva Canada Limited1997-01-16Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-flutamideTablet250 mgOralApotex Inc1998-10-08Not applicableCanada
FlutamideCapsule125 mg/1OralIVAX Pharmaceuticals, Inc.2001-09-19Not applicableUs
FlutamideCapsule125 mg/1OralActavis Pharma, Inc.2011-07-28Not applicableUs
FlutamideCapsule125 mg/1OralPar Pharmaceutical Inc.2001-09-18Not applicableUs
FlutamideCapsule125 mg/1OralCipla USA Inc.2016-09-21Not applicableUs
FlutamideCapsule125 mg/1OralGolden State Medical Supply, Inc.2001-09-18Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AndraxanCSC
AntiprosMedicamerc
CurestatAdvanced Pharmaceutical
CytomidCipla
DedileIvax
DrogenilBayer
ElbatGenepharm
EtaconilNolver
EulexinSchering-Plough
FarostatOrion
FlimutalCryopharma
FlucinomMerck Sharp & Dohme
FlulemTeva
OdyneNippon Kayaku
ProstadirexSanofi-Aventis
ProstanonPharmachemie
Brand mixturesNot Available
SaltsNot Available
Categories
UNII76W6J0943E
CAS number13311-84-7
WeightAverage: 276.2118
Monoisotopic: 276.072176843
Chemical FormulaC11H11F3N2O3
InChI KeyMKXKFYHWDHIYRV-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
IndicationFor the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate
Structured Indications
PharmacodynamicsFlutamide 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 actionFlutamide 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Androgen receptorProteinyes
antagonist
HumanP10275 details
Aryl hydrocarbon receptorProteinunknown
agonist
HumanP35869 details
Related Articles
AbsorptionRapidly and completely absorbed.
Volume of distributionNot Available
Protein binding94-96%
Metabolism

Flutamide is rapidly and extensively metabolized, with flutamide comprising only 2.5% of plasma radioactivity 1 hour after administration.

SubstrateEnzymesProduct
Flutamide
2-hydroxyflutamideDetails
Route of eliminationFlutamide 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 lifeThe plasma half-life for the alpha-hydroxylated metabolite of flutamide (an active metabolite) is approximately 6 hours.
ClearanceNot Available
ToxicityIn 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
AmiodaroneThe metabolism of Flutamide can be decreased when combined with Amiodarone.Approved, Investigational
AnvirzelAnvirzel may decrease the cardiotoxic activities of Flutamide.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
BexaroteneThe serum concentration of Flutamide can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Flutamide can be decreased when combined with Boceprevir.Approved
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
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
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
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
DexamethasoneThe serum concentration of Flutamide can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Flutamide.Approved
DigoxinDigoxin 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
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 serum concentration of Flutamide can be decreased when it is 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 serum concentration of Flutamide can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Flutamide can be decreased when combined with Esomeprazole.Approved, Investigational
EtravirineThe serum concentration of Flutamide can be decreased when it is 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
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
LidocaineThe metabolism of Flutamide can be decreased when combined with Lidocaine.Approved, Vet Approved
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
MexiletineThe metabolism of Flutamide can be decreased when combined with Mexiletine.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 serum concentration of Flutamide can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Flutamide can be decreased when it is combined with Nafcillin.Approved
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
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
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
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
RitonavirThe metabolism of Flutamide can be decreased when combined with Ritonavir.Approved, Investigational
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.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
TelithromycinThe metabolism of Flutamide can be decreased when combined with Telithromycin.Approved
TenofovirThe metabolism of Flutamide can be decreased when combined with Tenofovir.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
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
ATC CodesL02BB01
AHFS Codes
  • 10:00.00
PDB EntriesNot Available
FDA labelDownload (413 KB)
MSDSDownload (55.8 KB)
ADMET
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 )
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point111.5-112.5Gold, 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassN-arylamides
Sub ClassNot Available
Direct ParentN-arylamides
Alternative Parents
Substituents
  • N-arylamide
  • Nitrobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Organic nitrite
  • C-nitro compound
  • Carboxamide group
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Organic zwitterion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

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 factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
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 (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and matu...
Gene Name:
AHR
Uniprot ID:
P35869
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
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
substrateinhibitor
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 unrelated compounds, including steroids, fatty acids, retinoid and xenobiotics. Preferentially oxidizes 17beta-estradiol to the carcinogenic 4-hydroxy derivative, and a variety of procarcinogenic compou...
Gene Name:
CYP1B1
Uniprot ID:
Q16678
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 imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A5
Uniprot ID:
P20815
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23