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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 mgoralSchering Plough Canada Inc1996-12-312014-07-31Canada
Flutamidetablet250 mgoralPharmascience Inc1997-10-31Not applicableCanada
Flutamidetablet250 mgoralPharmel Inc1998-12-01Not applicableCanada
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/1oralWatson Laboratories, Inc.2011-07-28Not applicableUs
Flutamidecapsule125 mg/1oralPar Pharmaceutical Inc.2001-09-18Not 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 KeyInChIKey=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
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
Pharmacology
IndicationFor the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate
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.
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
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
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)
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Flutamide can be increased when it is combined with Abiraterone.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Flutamide.
AmiodaroneThe metabolism of Flutamide can be decreased when combined with Amiodarone.
AprepitantThe serum concentration of Flutamide can be increased when it is combined with Aprepitant.
ArmodafinilThe metabolism of Flutamide can be decreased when combined with Armodafinil.
AtazanavirThe metabolism of Flutamide can be decreased when combined with Atazanavir.
AtomoxetineThe metabolism of Flutamide can be decreased when combined with Atomoxetine.
AzithromycinThe metabolism of Flutamide can be decreased when combined with Azithromycin.
BevacizumabBevacizumab may increase the cardiotoxic activities of Flutamide.
BexaroteneThe serum concentration of Flutamide can be decreased when it is combined with Bexarotene.
BoceprevirThe metabolism of Flutamide can be decreased when combined with Boceprevir.
BortezomibThe metabolism of Flutamide can be decreased when combined with Bortezomib.
BosentanThe serum concentration of Flutamide can be decreased when it is combined with Bosentan.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Flutamide.
CaffeineThe metabolism of Flutamide can be decreased when combined with Caffeine.
CarbamazepineThe metabolism of Flutamide can be increased when combined with Carbamazepine.
CeritinibThe serum concentration of Flutamide can be increased when it is combined with Ceritinib.
ChloramphenicolThe metabolism of Flutamide can be decreased when combined with Chloramphenicol.
CholecalciferolThe metabolism of Flutamide can be decreased when combined with Cholecalciferol.
Choline C 11The therapeutic efficacy of Choline C 11 can be decreased when used in combination with Flutamide.
CimetidineThe metabolism of Flutamide can be decreased when combined with Cimetidine.
CitalopramThe metabolism of Flutamide can be decreased when combined with Citalopram.
ClarithromycinThe metabolism of Flutamide can be decreased when combined with Clarithromycin.
ClemastineThe metabolism of Flutamide can be decreased when combined with Clemastine.
ClotrimazoleThe metabolism of Flutamide can be decreased when combined with Clotrimazole.
CobicistatThe metabolism of Flutamide can be decreased when combined with Cobicistat.
ConivaptanThe serum concentration of Flutamide can be increased when it is combined with Conivaptan.
CrizotinibThe metabolism of Flutamide can be decreased when combined with Crizotinib.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Flutamide.
CyclosporineThe metabolism of Flutamide can be decreased when combined with Cyclosporine.
Cyproterone acetateThe serum concentration of Flutamide can be decreased when it is combined with Cyproterone acetate.
DabrafenibThe serum concentration of Flutamide can be decreased when it is combined with Dabrafenib.
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Flutamide.
DarunavirThe metabolism of Flutamide can be decreased when combined with Darunavir.
DasatinibThe serum concentration of Flutamide can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Flutamide can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Flutamide can be decreased when combined with Delavirdine.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Flutamide.
DexamethasoneThe serum concentration of Flutamide can be decreased when it is combined with Dexamethasone.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Flutamide.
DigoxinDigoxin may decrease the cardiotoxic activities of Flutamide.
DihydroergotamineThe metabolism of Flutamide can be decreased when combined with Dihydroergotamine.
DiltiazemThe metabolism of Flutamide can be decreased when combined with Diltiazem.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Flutamide.
DoxycyclineThe metabolism of Flutamide can be decreased when combined with Doxycycline.
DronedaroneThe metabolism of Flutamide can be decreased when combined with Dronedarone.
EfavirenzThe serum concentration of Flutamide can be decreased when it is combined with Efavirenz.
EnzalutamideThe serum concentration of Flutamide can be decreased when it is combined with Enzalutamide.
ErythromycinThe metabolism of Flutamide can be decreased when combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Flutamide can be decreased when it is combined with Eslicarbazepine acetate.
EsomeprazoleThe metabolism of Flutamide can be decreased when combined with Esomeprazole.
EtravirineThe serum concentration of Flutamide can be decreased when it is combined with Etravirine.
FluconazoleThe metabolism of Flutamide can be decreased when combined with Fluconazole.
FluoxetineThe metabolism of Flutamide can be decreased when combined with Fluoxetine.
FluvoxamineThe metabolism of Flutamide can be decreased when combined with Fluvoxamine.
FosamprenavirThe metabolism of Flutamide can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Flutamide can be increased when it is combined with Fosaprepitant.
FosphenytoinThe metabolism of Flutamide can be increased when combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Flutamide can be increased when it is combined with Fusidic Acid.
GemfibrozilThe metabolism of Flutamide can be decreased when combined with Gemfibrozil.
IdelalisibThe serum concentration of Flutamide can be increased when it is combined with Idelalisib.
ImatinibThe metabolism of Flutamide can be decreased when combined with Imatinib.
IndinavirThe metabolism of Flutamide can be decreased when combined with Indinavir.
IsavuconazoniumThe metabolism of Flutamide can be decreased when combined with Isavuconazonium.
IsoniazidThe metabolism of Flutamide can be decreased when combined with Isoniazid.
IsradipineThe metabolism of Flutamide can be decreased when combined with Isradipine.
ItraconazoleThe metabolism of Flutamide can be decreased when combined with Itraconazole.
IvacaftorThe serum concentration of Flutamide can be increased when it is combined with Ivacaftor.
KetoconazoleThe metabolism of Flutamide can be decreased when combined with Ketoconazole.
LidocaineThe metabolism of Flutamide can be decreased when combined with Lidocaine.
LopinavirThe metabolism of Flutamide can be decreased when combined with Lopinavir.
LovastatinThe metabolism of Flutamide can be decreased when combined with Lovastatin.
LuliconazoleThe serum concentration of Flutamide can be increased when it is combined with Luliconazole.
LumacaftorThe serum concentration of Flutamide can be decreased when it is combined with Lumacaftor.
MexiletineThe metabolism of Flutamide can be decreased when combined with Mexiletine.
MifepristoneThe metabolism of Flutamide can be decreased when combined with Mifepristone.
MitotaneThe serum concentration of Flutamide can be decreased when it is combined with Mitotane.
MoclobemideThe metabolism of Flutamide can be decreased when combined with Moclobemide.
ModafinilThe serum concentration of Flutamide can be decreased when it is combined with Modafinil.
NafcillinThe serum concentration of Flutamide can be decreased when it is combined with Nafcillin.
NefazodoneThe metabolism of Flutamide can be decreased when combined with Nefazodone.
NelfinavirThe metabolism of Flutamide can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Flutamide can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Flutamide can be decreased when combined with Nevirapine.
NicardipineThe metabolism of Flutamide can be decreased when combined with Nicardipine.
NilotinibThe metabolism of Flutamide can be decreased when combined with Nilotinib.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Flutamide.
OlaparibThe metabolism of Flutamide can be decreased when combined with Olaparib.
OmeprazoleThe metabolism of Flutamide can be decreased when combined with Omeprazole.
OsimertinibThe serum concentration of Flutamide can be increased when it is combined with Osimertinib.
OuabainOuabain may decrease the cardiotoxic activities of Flutamide.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Flutamide.
PalbociclibThe serum concentration of Flutamide can be increased when it is combined with Palbociclib.
PantoprazoleThe metabolism of Flutamide can be decreased when combined with Pantoprazole.
Peginterferon alfa-2bThe serum concentration of Flutamide can be increased when it is combined with Peginterferon alfa-2b.
PentobarbitalThe metabolism of Flutamide can be increased when combined with Pentobarbital.
PhenobarbitalThe metabolism of Flutamide can be increased when combined with Phenobarbital.
PhenytoinThe metabolism of Flutamide can be increased when combined with Phenytoin.
PosaconazoleThe metabolism of Flutamide can be decreased when combined with Posaconazole.
PrilocaineThe risk or severity of adverse effects can be increased when Flutamide is combined with Prilocaine.
PrimidoneThe metabolism of Flutamide can be increased when combined with Primidone.
RanolazineThe metabolism of Flutamide can be decreased when combined with Ranolazine.
RifabutinThe metabolism of Flutamide can be increased when combined with Rifabutin.
RifampicinThe metabolism of Flutamide can be increased when combined with Rifampicin.
RifapentineThe metabolism of Flutamide can be increased when combined with Rifapentine.
RitonavirThe metabolism of Flutamide can be decreased when combined with Ritonavir.
RopiniroleThe metabolism of Flutamide can be decreased when combined with Ropinirole.
SaquinavirThe metabolism of Flutamide can be decreased when combined with Saquinavir.
SertralineThe metabolism of Flutamide can be decreased when combined with Sertraline.
SildenafilThe metabolism of Flutamide can be decreased when combined with Sildenafil.
SiltuximabThe serum concentration of Flutamide can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Flutamide can be increased when it is combined with Simeprevir.
Sodium NitriteThe risk or severity of adverse effects can be increased when Flutamide is combined with Sodium Nitrite.
St. John's WortThe serum concentration of Flutamide can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Flutamide can be increased when it is combined with Stiripentol.
SulfisoxazoleThe metabolism of Flutamide can be decreased when combined with Sulfisoxazole.
TelaprevirThe metabolism of Flutamide can be decreased when combined with Telaprevir.
TelithromycinThe metabolism of Flutamide can be decreased when combined with Telithromycin.
TenofovirThe metabolism of Flutamide can be decreased when combined with Tenofovir.
TeriflunomideThe serum concentration of Flutamide can be decreased when it is combined with Teriflunomide.
TheophyllineThe metabolism of Flutamide can be decreased when combined with Theophylline.
TiclopidineThe metabolism of Flutamide can be decreased when combined with Ticlopidine.
TocilizumabThe serum concentration of Flutamide can be decreased when it is combined with Tocilizumab.
TopiramateThe metabolism of Flutamide can be decreased when combined with Topiramate.
TranylcypromineThe metabolism of Flutamide can be decreased when combined with Tranylcypromine.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Flutamide.
VemurafenibThe serum concentration of Flutamide can be increased when it is combined with Vemurafenib.
VenlafaxineThe metabolism of Flutamide can be decreased when combined with Venlafaxine.
VerapamilThe metabolism of Flutamide can be decreased when combined with Verapamil.
VoriconazoleThe metabolism of Flutamide can be decreased when combined with Voriconazole.
ZiprasidoneThe metabolism of Flutamide can be decreased when combined with Ziprasidone.
Food Interactions
  • Take without regard to meals.

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