FLUTAMIDE

Search structure
Trade Names:
Synonyms:
Status: Approved (1989)
Entry Type: Small molecule
Molecule Category: Parent Prodrug
ATC: L02BB01
UNII: 76W6J0943E

Structure
InChI Key MKXKFYHWDHIYRV-UHFFFAOYSA-N
Smile CC(C)C(=O)Nc1ccc([N+](=O)[O-])c(C(F)(F)F)c1
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C11H11F3N2O3
Molecular Weight 276.21
AlogP 3.21
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 72.24
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 19.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.35 - EXP
Henry's Law Constant 3.73E-10 atm-m3/mole EST
Atmospheric OH Rate Constant 2.75E-12 cm3/molecule-sec EST
Water Solubility 9.450 mg/L EST
Vapor Pressure 1.11E-06 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Androgen Receptor antagonist FDA
Primary Target
Androgen receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- - - 600-14000 -
Enzyme Oxidoreductase
- - - - 11-19
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
- 154-4200 - 1300-3700 12-20
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 7-131
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 34
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 50000-75000 - - -

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
Polycystic Ovary Syndrome 2 D011085 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Adrenal Hyperplasia, Congenital 2 D000312 ClinicalTrials

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Hepatobiliary disorders
17.04
General disorders and administration site conditions
15.56
Injury, poisoning and procedural complications
8.89
Skin and subcutaneous tissue disorders
8.89
Nervous system disorders
8.15
Respiratory, thoracic and mediastinal disorders
6.67
Investigations
5.93
Blood and lymphatic system disorders
3.7
Gastrointestinal disorders
3.7
Immune system disorders
3.7
Renal and urinary disorders
3.7
Reproductive system and breast disorders
3.7
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.96
Endocrine disorders
2.22
Infections and infestations
2.22
Metabolism and nutrition disorders
2.22

Cross References

Resources Reference
CAS NUMBER 13311-84-7
ChEBI 5132
ChEMBL CHEMBL806
DrugBank DB00499
DrugCentral 1223
EPA CompTox DTXSID7032004
FDA SRS 76W6J0943E
Human Metabolome Database HMDB0014642
Guide to Pharmacology 6943
KEGG C07653
PharmGKB PA449685
PubChem 3397
SureChEMBL SCHEMBL3934
ZINC ZINC000003812944
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