NILUTAMIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1996)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L02BB02
UNII: 51G6I8B902

Structure
InChI Key XWXYUMMDTVBTOU-UHFFFAOYSA-N
Smile CC1(C)NC(=O)N(c2ccc([N+](=O)[O-])c(C(F)(F)F)c2)C1=O
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H10F3N3O4
Molecular Weight 317.22
AlogP 2.45
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 92.55
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 22.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Androgen Receptor antagonist DailyMed
Primary Target
Androgen receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- - - - 98
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 9-600 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 117

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Prostatic Neoplasms 4 D011471 ClinicalTrials
Prostatic Neoplasms 4 D011471 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 3 D064129 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
General disorders and administration site conditions Hot flush 28.4
Reproductive system and breast disorders Menopausal symptoms 28.4
General disorders and administration site conditions Hot flush
Reproductive system and breast disorders Menopausal symptoms
Gastrointestinal disorders Nausea 9.8
Infections and infestations Urinary tract infection
Investigations Aspartate aminotransferase increased 8.0
Infections and infestations Urinary tract infection 8.0
Investigations Alanine aminotransferase increased 7.6
Cardiac disorders Dyspnoea
Gastrointestinal disorders Constipation 7.1
Cardiac disorders Dizziness 7.1
Eye disorders Visual impairment 6.7
Cardiac disorders Dyspnoea 6.2
Gastrointestinal disorders Nausea
Vascular disorders Hypertension 5.3
Metabolism and nutrition disorders Alcohol intolerance 5.0
Investigations Alanine aminotransferase increased
Endocrine disorders Hyperglycaemia 4.0
Respiratory, thoracic and mediastinal disorders Lung disorder 4.0
Investigations Aspartate aminotransferase increased
Gastrointestinal disorders Constipation
Cardiac disorders Dizziness
Investigations Blood alkaline phosphatase increased 3.0
Cardiac disorders Cardiac failure 3.0
Blood and lymphatic system disorders Leukopenia 3.0
Nervous system disorders Paraesthesia 3.0
Vascular disorders Hypertension
Cardiac disorders Angina pectoris 2.0
Musculoskeletal and connective tissue disorders Arthritis 2.0
Investigations Blood creatinine increased 2.0
Investigations Blood urea increased 2.0
Eye disorders Cataract 2.0
Respiratory, thoracic and mediastinal disorders Cough 2.0
Gastrointestinal disorders Diarrhoea 2.0
General disorders and administration site conditions Discomfort 2.0
Cardiac disorders Dizziness 2.0
Gastrointestinal disorders Dry mouth 2.0
General disorders and administration site conditions Feeling abnormal 2.0
Gastrointestinal disorders Gastrointestinal disorder 2.0
Gastrointestinal disorders Gastrointestinal haemorrhage 2.0
Investigations Haptoglobin increased 2.0
General disorders and administration site conditions Ill-defined disorder 2.0
Immune system disorders Interstitial lung disease 2.0
Nervous system disorders Loss of consciousness 2.0
General disorders and administration site conditions Malaise 2.0
Gastrointestinal disorders Melaena 2.0
Psychiatric disorders Nervousness 2.0
General disorders and administration site conditions Oedema 2.0
Eye disorders Photophobia 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Infections and infestations Rhinitis 2.0
Vascular disorders Shock 2.0
Cardiac disorders Syncope 2.0
Psychiatric disorders Tension 2.0
Investigations Weight decreased 2.0
Eye disorders Visual impairment

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
19.3
Respiratory, thoracic and mediastinal disorders
19.3
Investigations
11.4
Nervous system disorders
10.53
Cardiac disorders
7.89
Metabolism and nutrition disorders
5.26
Immune system disorders
3.51
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
3.51
Gastrointestinal disorders
2.63
Reproductive system and breast disorders
2.63
Vascular disorders
2.63

Cross References

Resources Reference
CAS NUMBER 63612-50-0
ChEBI 7573
ChEMBL CHEMBL1274
DrugBank DB00665
DrugCentral 1933
EPA CompTox DTXSID3034165
FDA SRS 51G6I8B902
Human Metabolome Database HMDB0014803
Guide to Pharmacology 2864
KEGG C08164
PharmGKB PA450632
PubChem 4493
SureChEMBL SCHEMBL12670
ZINC ZINC000003874498
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