Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:41 UTC
HMDB IDHMDB0014642
Secondary Accession Numbers
  • HMDB14642
Metabolite Identification
Common NameFlutamide
DescriptionFlutamide is only found in individuals that have used or taken this drug. It is an antiandrogen with about the same potency as cyproterone in rodent and canine species.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.
Structure
Data?1582753202
Synonyms
ValueSource
4'-Nitro-3'-trifluoromethylisobutyranilideChEBI
alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-propionotoluidideChEBI
EulexinChEBI
FlutamidaChEBI
FlutamidumChEBI
NiftolidChEBI
NiftolideChEBI
a,a,a-Trifluoro-2-methyl-4'-nitro-m-propionotoluidideGenerator
Α,α,α-trifluoro-2-methyl-4'-nitro-m-propionotoluidideGenerator
Flutamide usp25HMDB
EuflexHMDB
EulexineHMDB
FlukenHMDB
FlulemHMDB
Fluta cellHMDB
Fluta-gryHMDB
FlutaplexHMDB
FugerelHMDB
Juta brand OF flutamideHMDB
Novo flutamideHMDB
PMS-FlutamideHMDB
Pharmascience brand OF flutamideHMDB
Prasfarma brand OF flutamideHMDB
ProsticaHMDB
Schering brand OF flutamideHMDB
Schering-plough brand OF flutamideHMDB
TAD brand OF flutamideHMDB
Cell pharm brand OF flutamideHMDB
1a Brand OF flutamideHMDB
Apo flutamideHMDB
Apogepha brand OF flutamideHMDB
ChimaxHMDB
CytamidHMDB
Fluta gryHMDB
Fluta-cellHMDB
FlutacellHMDB
GrisetinHMDB
Gry brand OF flutamideHMDB
Lemery brand OF flutamideHMDB
Q Pharm brand OF flutamideHMDB
Apo-flutamideHMDB
Ciclum brand OF flutamideHMDB
DrogenilHMDB
FlumidHMDB
FlutaGRYHMDB
FlutexinHMDB
Inibsa brand OF flutamideHMDB
Ipsen brand OF flutamideHMDB
PMS FlutamideHMDB
ProstacurHMDB
ProstogenatHMDB
TestotardHMDB
Esparma brand OF flutamideHMDB
Alphapharm brand OF flutamideHMDB
ApimidHMDB
ApoFlutamideHMDB
Apotex brand OF flutamideHMDB
Azupharma brand OF flutamideHMDB
Chephasaar brand OF flutamideHMDB
Chiron brand OF flutamideHMDB
Essex brand OF flutamideHMDB
Fluta 1a pharmaHMDB
FlutaminHMDB
FlutandronaHMDB
Hexal brand OF flutamideHMDB
Kendrick brand OF flutamideHMDB
Novo-flutamideHMDB
NovoFlutamideHMDB
Novopharm brand OF flutamideHMDB
OncosalHMDB
Q-Pharm brand OF flutamideHMDB
Schering plough brand OF flutamideHMDB
Tedec meiji brand OF flutamideHMDB
Chemical FormulaC11H11F3N2O3
Average Molecular Weight276.2118
Monoisotopic Molecular Weight276.072176843
IUPAC Name2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Traditional Nameflutamide
CAS Registry Number13311-84-7
SMILES
CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F
InChI Identifier
InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
InChI KeyMKXKFYHWDHIYRV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassTrifluoromethylbenzenes
Direct ParentTrifluoromethylbenzenes
Alternative Parents
Substituents
  • Trifluoromethylbenzene
  • Nitrobenzene
  • Anilide
  • N-arylamide
  • Nitroaromatic compound
  • Carboxamide group
  • C-nitro compound
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Alkyl halide
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organic oxygen compound
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Alkyl fluoride
  • Organic zwitterion
  • Carbonyl group
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point111 - 113 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0057 g/LNot Available
LogP2.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available160.022http://allccs.zhulab.cn/database/detail?ID=AllCCS00000829
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP2.55ALOGPS
logP3.27ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.17ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity63.42 m³·mol⁻¹ChemAxon
Polarizability23.2 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+163.90130932474
DeepCCS[M-H]-161.15630932474
DeepCCS[M-2H]-195.94530932474
DeepCCS[M+Na]+172.15430932474
AllCCS[M+H]+157.032859911
AllCCS[M+H-H2O]+153.532859911
AllCCS[M+NH4]+160.232859911
AllCCS[M+Na]+161.132859911
AllCCS[M-H]-156.332859911
AllCCS[M+Na-2H]-156.132859911
AllCCS[M+HCOO]-156.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FlutamideCC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F2269.6Standard polar33892256
FlutamideCC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F1959.3Standard non polar33892256
FlutamideCC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F1927.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Flutamide,1TMS,isomer #1CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C1708.9Semi standard non polar33892256
Flutamide,1TMS,isomer #1CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C1797.7Standard non polar33892256
Flutamide,1TMS,isomer #1CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C1842.8Standard polar33892256
Flutamide,1TBDMS,isomer #1CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C1984.1Semi standard non polar33892256
Flutamide,1TBDMS,isomer #1CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C1996.3Standard non polar33892256
Flutamide,1TBDMS,isomer #1CC(C)C(=O)N(C1=CC=C([N+](=O)[O-])C(C(F)(F)F)=C1)[Si](C)(C)C(C)(C)C1961.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Flutamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9280000000-95879ab49ae3474dd1342017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flutamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flutamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide LC-ESI-qTof , Positive-QTOFsplash10-004i-0290000000-cca4c08f2a9bb3fc6f572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide LC-ESI-qTof , Positive-QTOFsplash10-004i-0190000000-df05faf7e38e6d6da2032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide LC-ESI-qTof , Positive-QTOFsplash10-000i-3900000000-8b7e5888950eed07b29b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide LC-ESI-QFT , negative-QTOFsplash10-004i-0090000000-983edf51e9c479db69a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide , positive-QTOFsplash10-004i-0190000000-df05faf7e38e6d6da2032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide , positive-QTOFsplash10-004i-0290000000-cca4c08f2a9bb3fc6f572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide , positive-QTOFsplash10-03di-2940000000-170008eb50a63f0664d02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 90V, Negative-QTOFsplash10-0gx0-1900000000-c322f29e305a6d10044c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 50V, Positive-QTOFsplash10-014i-0940000000-8c0e8ce0c0167f8242102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 10V, Negative-QTOFsplash10-004i-0090000000-3ec575077e4f9903d0af2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 50V, Positive-QTOFsplash10-014i-0940000000-5a90366233a8102519232021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 30V, Negative-QTOFsplash10-0udi-0390000000-bb6d9f3ab642b5c061ba2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 20V, Negative-QTOFsplash10-004i-0090000000-cdcab2cffbd217c82fad2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 40V, Positive-QTOFsplash10-014i-0920000000-3d0edd4f5b6b7545a7f32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 60V, Negative-QTOFsplash10-0udi-0890000000-9c05c9f4c668a596f70e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 30V, Positive-QTOFsplash10-014i-0910000000-abf238316a2db628c1542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 40V, Positive-QTOFsplash10-014i-0920000000-9eb906d56b8ae34b46812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 75V, Negative-QTOFsplash10-0il0-0920000000-a14d1afe6adfae49f6ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Flutamide 45V, Negative-QTOFsplash10-0ufr-0190000000-0c4cfbc09b7620965ab52021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flutamide 10V, Positive-QTOFsplash10-004i-0090000000-7122c7547dc4f518e9fa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flutamide 20V, Positive-QTOFsplash10-00kf-8090000000-02b603738815e91326c22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flutamide 40V, Positive-QTOFsplash10-006x-9010000000-19ee080aa7e8861af1ff2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flutamide 10V, Negative-QTOFsplash10-004i-0090000000-e5a1eaa719d4f63bf6f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flutamide 20V, Negative-QTOFsplash10-004i-2090000000-13768fb84641e8448d752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flutamide 40V, Negative-QTOFsplash10-0076-9000000000-10b226e4bd1f69316fa12016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00499 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00499 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00499
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3280
KEGG Compound IDC07653
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFlutamide
METLIN IDNot Available
PubChem Compound3397
PDB IDNot Available
ChEBI ID5132
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. BC Cancer Agency [Link]

Enzymes

General function:
Involved in monooxygenase 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 xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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 ]
General function:
Involved in monooxygenase 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:
55944.565
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 ]
General function:
Involved in monooxygenase 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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
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 ]
General function:
Involved in monooxygenase 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:
CYP3A5
Uniprot ID:
P20815
Molecular weight:
57108.065
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 ]
General function:
Involved in monooxygenase 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
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 ]
General function:
Involved in monooxygenase 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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
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 ]
General function:
Involved in DNA 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
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9
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 ]
General function:
Involved in transcription regulator activity
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 maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7
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 ]