U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H11F3N2O3
Molecular Weight 276.2118
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTAMIDE

SMILES

CC(C)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

InChI

InChIKey=MKXKFYHWDHIYRV-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description

Flutamide 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. Flutamide 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. Flutamide is used for the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.9 µM [IC50]
102.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EULEXIN

Cmax

ValueDoseCo-administeredAnalytePopulation
2.42 μg/mL
500 mg single, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens
53.4 ng/mL
250 mg single, oral
FLUTAMIDE plasma
Homo sapiens
25.2 ng/mL
250 mg single, oral
FLUTAMIDE plasma
Homo sapiens
112.7 ng/mL
250 mg 3 times / day steady-state, oral
FLUTAMIDE plasma
Homo sapiens
1629 ng/mL
250 mg 3 times / day steady-state, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens
967 ng/mL
250 mg single, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
24.3 μg × h/mL
500 mg single, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens
4 μg × h/mL
250 mg 3 times / day multiple, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens
96.4 ng × h/mL
250 mg single, oral
FLUTAMIDE plasma
Homo sapiens
63 ng × h/mL
250 mg single, oral
FLUTAMIDE plasma
Homo sapiens
212.1 ng × h/mL
250 mg 3 times / day steady-state, oral
FLUTAMIDE plasma
Homo sapiens
4993 ng × h/mL
250 mg single, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
13.3 h
500 mg single, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens
9.6 h
250 mg 3 times / day steady-state, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens
7.1 h
250 mg single, oral
HYDROXYFLUTAMIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
250 mg single, oral
FLUTAMIDE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
For use in locally confined stage B2-C and stage D2 metastatic carcinoma of the prostate: 250 mg orally every 8 hours.
Route of Administration: Oral
In Vitro Use Guide
Flutamide inhibited spiggin production in vitro at a concentration as low as 10(-12) M in cultures of primed female stickleback kidney cells