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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:45 UTC
HMDB IDHMDB0014803
Secondary Accession Numbers
  • HMDB14803
Metabolite Identification
Common NameNilutamide
DescriptionNilutamide is an antineoplastic hormonal agent primarily used in the treatment of prostate cancer. Nilutamide is a pure, nonsteroidal anti-androgen with affinity for androgen receptors (but not for progestogen, estrogen, or glucocorticoid receptors). Consequently, Nilutamide blocks the action of androgens of adrenal and testicular origin that stimulate the growth of normal and malignant prostatic tissue. Prostate cancer is mostly androgen-dependent and can be treated with surgical or chemical castration. To date, antiandrogen monotherapy has not consistently been shown to be equivalent to castration.
Structure
Data?1582753222
Synonyms
ValueSource
5,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoinChEBI
NilandronChEBI
NilutamidaChEBI
NilutamidumChEBI
5,5-Dimethyl-3-(a,a,a-trifluoro-4-nitro-m-tolyl)hydantoinGenerator
5,5-Dimethyl-3-(α,α,α-trifluoro-4-nitro-m-tolyl)hydantoinGenerator
5,5-Dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)- 2,4-imidazolidinedioneHMDB
Hoechst brand OF nilutamideHMDB
Aventis behring brand OF nilutamideHMDB
Aventis brand OF nilutamideHMDB
AnandronHMDB
Chemical FormulaC12H10F3N3O4
Average Molecular Weight317.2207
Monoisotopic Molecular Weight317.062340438
IUPAC Name5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
Traditional Namenilutamide
CAS Registry Number63612-50-0
SMILES
CC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F
InChI Identifier
InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)
InChI KeyXWXYUMMDTVBTOU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentPhenylhydantoins
Alternative Parents
Substituents
  • 3-phenylhydantoin
  • Phenylimidazolidine
  • Alpha-amino acid or derivatives
  • Trifluoromethylbenzene
  • Nitrobenzene
  • Nitroaromatic compound
  • N-acyl urea
  • Ureide
  • Monocyclic benzene moiety
  • Benzenoid
  • Dicarboximide
  • Organic nitro compound
  • C-nitro compound
  • Carbonic acid derivative
  • Urea
  • Azacycle
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Carbonyl group
  • Organohalogen compound
  • Organic zwitterion
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alkyl fluoride
  • Organic nitrogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Alkyl halide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0042 g/LNot Available
LogP1.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP1.74ALOGPS
logP2.25ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)15.01ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area95.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.23 m³·mol⁻¹ChemAxon
Polarizability25.88 ųChemAxon
Number of Rings2ChemAxon
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]+169.72430932474
DeepCCS[M-H]-166.05530932474
DeepCCS[M-2H]-202.18430932474
DeepCCS[M+Na]+178.2930932474
AllCCS[M+H]+165.432859911
AllCCS[M+H-H2O]+162.132859911
AllCCS[M+NH4]+168.432859911
AllCCS[M+Na]+169.332859911
AllCCS[M-H]-164.332859911
AllCCS[M+Na-2H]-163.632859911
AllCCS[M+HCOO]-163.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NilutamideCC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F2457.5Standard polar33892256
NilutamideCC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F2253.6Standard non polar33892256
NilutamideCC1(C)NC(=O)N(C1=O)C1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F2159.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nilutamide,1TMS,isomer #1CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C2044.1Semi standard non polar33892256
Nilutamide,1TMS,isomer #1CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C2157.3Standard non polar33892256
Nilutamide,1TMS,isomer #1CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C2480.6Standard polar33892256
Nilutamide,1TBDMS,isomer #1CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C(C)(C)C2322.7Semi standard non polar33892256
Nilutamide,1TBDMS,isomer #1CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C(C)(C)C2357.6Standard non polar33892256
Nilutamide,1TBDMS,isomer #1CC1(C)C(=O)N(C2=CC=C([N+](=O)[O-])C(C(F)(F)F)=C2)C(=O)N1[Si](C)(C)C(C)(C)C2522.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nilutamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a59-9051000000-b212093377487cffc1582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nilutamide 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 - Nilutamide 30V, Negative-QTOFsplash10-0600-0094000000-0991ece9f9d42b94c6432021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nilutamide 15V, Negative-QTOFsplash10-014i-0019000000-7989a507a8031f03f6122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nilutamide 45V, Negative-QTOFsplash10-00di-0090000000-1d63c70e06fcd4c6d9222021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nilutamide 60V, Negative-QTOFsplash10-0kmi-0390000000-05fc687a7f642e06e60a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nilutamide 60V, Positive-QTOFsplash10-0kmi-0390000000-e2d42b542bf6dc07d5c02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nilutamide 75V, Negative-QTOFsplash10-0zfr-1970000000-f1091bfdddddc602902c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Nilutamide 90V, Negative-QTOFsplash10-0lz9-1920000000-14b049879972342182672021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nilutamide 10V, Positive-QTOFsplash10-014i-0009000000-f4acafe069c7fdcf8fc32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nilutamide 20V, Positive-QTOFsplash10-0a4i-9025000000-2c79c0bbfc87dd118bd72016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nilutamide 40V, Positive-QTOFsplash10-0a4l-9000000000-a91f0e83aff94e2bad182016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nilutamide 10V, Negative-QTOFsplash10-014i-0009000000-19746ba07e5113297e152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nilutamide 20V, Negative-QTOFsplash10-014i-4009000000-f2904499b324cc347c222016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nilutamide 40V, Negative-QTOFsplash10-0a4l-9000000000-740d06c64bdf821f7e3d2016-08-03Wishart 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 DB00665 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00665 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 IDDB00665
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4337
KEGG Compound IDC08164
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNilutamide
METLIN IDNot Available
PubChem Compound4493
PDB IDNot Available
ChEBI ID7573
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. Kassouf W, Tanguay S, Aprikian AG: Nilutamide as second line hormone therapy for prostate cancer after androgen ablation fails. J Urol. 2003 May;169(5):1742-4. [PubMed:12686822 ]
  2. Lukka H, Waldron T, Klotz L, Winquist E, Trachtenberg J: Maximal androgen blockade for the treatment of metastatic prostate cancer--a systematic review. Curr Oncol. 2006 Jun;13(3):81-93. [PubMed:17576447 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name:
POR
Uniprot ID:
P16435
Molecular weight:
77047.575
References
  1. Berger V, Berson A, Wolf C, Chachaty C, Fau D, Fromenty B, Pessayre D: Generation of free radicals during the reductive metabolism of nilutamide by lung microsomes: possible role in the development of lung lesions in patients treated with this anti-androgen. Biochem Pharmacol. 1992 Feb 4;43(3):654-7. [PubMed:1311586 ]
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
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. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
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 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. Raynaud JP: Antiandrogens in combination with LH-RH agonists in prostate cancer. Am J Clin Oncol. 1988;11 Suppl 2:S132-47. [PubMed:3071951 ]
  2. Moguilewsky M, Bertagna C, Hucher M: Pharmacological and clinical studies of the antiandrogen Anandron. J Steroid Biochem. 1987;27(4-6):871-5. [PubMed:3320565 ]
  3. Raynaud JP, Bonne C, Moguilewsky M, Lefebvre FA, Belanger A, Labrie F: The pure antiandrogen RU 23908 (Anandron), a candidate of choice for the combined antihormonal treatment of prostatic cancer: a review. Prostate. 1984;5(3):299-311. [PubMed:6374639 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  5. Labrie F: Hormonal therapy of prostate cancer. Prog Brain Res. 2010;182:321-41. doi: 10.1016/S0079-6123(10)82014-X. [PubMed:20541672 ]
  6. Schasfoort EM, Van De Beek C, Newling DW: Safety and efficacy of a non-steroidal anti-androgen, based on results of a post marketing surveillance of nilutamide. Prostate Cancer Prostatic Dis. 2001;4(2):112-117. [PubMed:12497048 ]
  7. Kaisary AV, Iversen P, Tyrrell CJ, Carroll K, Morris T: Is there a role for antiandrogen monotherapy in patients with metastatic prostate cancer? Prostate Cancer Prostatic Dis. 2001;4(4):196-203. [PubMed:12497018 ]
  8. Kolvenbag GJ, Furr BJ, Blackledge GR: Receptor affinity and potency of non-steroidal antiandrogens: translation of preclinical findings into clinical activity. Prostate Cancer Prostatic Dis. 1998 Dec;1(6):307-314. [PubMed:12496872 ]
  9. Brawer MK, Crawford ED, Labrie F, Mendoza-Valdes A, Miller PD, Petrylak DP: Androgen deprivation and other treatments for advanced prostate cancer. Rev Urol. 2001;3 Suppl 2:S59-68. [PubMed:16986000 ]