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

Details

Stereochemistry ACHIRAL
Molecular Formula C11H11F3N2O3
Molecular Weight 276.2123
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUTAMIDE

SMILES

CC(C)C(=Nc1ccc(c(c1)C(F)(F)F)N(=O)=O)O

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

Molecular Formula C11H11F3N2O3
Molecular Weight 276.2123
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/flutamide.html

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

Curator's Comment:: flutamide crosses the blood brain barrier and is capable of exerting influence on central structures through interactions with androgen receptors.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL612518
0.9 µM [IC50]
102.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
EULEXIN

Approved Use

Flutamide capsules are indicated for use in combination with LHRH agonists for the management of locally confined Stage B2-C and Stage D2 metastatic carcinoma of the prostate.

Launch Date

6.01776E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
53.4 ng/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
112.7 ng/mL
250 mg 3 times / day steady-state, oral
dose: 250 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
25.2 ng/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
96.4 ng × h/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
212.1 ng × h/mL
250 mg 3 times / day steady-state, oral
dose: 250 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FLUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
63 ng × h/mL
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
250 mg single, oral
dose: 250 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
FLUTAMIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Disc. AE: Abdominal pain, Vomiting...
Other AEs: Flatulence, Diarrhea...
AEs leading to
discontinuation/dose reduction:
Abdominal pain (12 patients)
Vomiting (8 patients)
Headache (9 patients)
Hypertransaminasemia (3 patients)
Fatty liver (1 patient)
Weight gain (5 patients)
Other AEs:
Flatulence (15 patients)
Diarrhea (5 patients)
Dry skin (10 patients)
Nephrolithiasis (1 patient)
Leg pain (2 patients)
Dyslipidemia (4 patients)
Fluid retention (4 patients)
Epigastralgia (3 patients)
Dyspepsia (2 patients)
Nausea (9 patients)
Vaginal infection (1 patient)
Constipation (3 patients)
Sources:
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Disc. AE: Diarrhea, Impaired liver function...
Other AEs: Hot flushes, Breast tenderness...
AEs leading to
discontinuation/dose reduction:
Diarrhea (severe, 1.3%)
Impaired liver function (4%)
Gynecomastia (1.3%)
Other AEs:
Hot flushes (all grades, 25%)
Breast tenderness (all grades, 49%)
Nausea and vomiting (all grades, 22%)
Appetite lost (all grades, 17%)
Diarrhea (all grades, 16%)
Hot flushes (severe, 4%)
Breast tenderness (severe, 7%)
Nausea and vomiting (severe, 1.3%)
Appetite lost (severe, 1.3%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nephrolithiasis 1 patient
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Vaginal infection 1 patient
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Fatty liver 1 patient
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Dry skin 10 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Abdominal pain 12 patients
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Flatulence 15 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Dyspepsia 2 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Leg pain 2 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Constipation 3 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Epigastralgia 3 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Hypertransaminasemia 3 patients
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Dyslipidemia 4 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Fluid retention 4 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Diarrhea 5 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Weight gain 5 patients
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Vomiting 8 patients
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Nausea 9 patients
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Headache 9 patients
Disc. AE
250 mg 1 times / day multiple, oral
Recommended
Dose: 250 mg, 1 times / day
Route: oral
Route: multiple
Dose: 250 mg, 1 times / day
Co-administed with::
ethinyl estradiol(0.020 mg)
desogestrel(0.15 mg)
Sources:
unhealthy, 26.3
n = 83
Health Status: unhealthy
Condition: hirsutism
Age Group: 26.3
Sex: F
Population Size: 83
Sources:
Gynecomastia 1.3%
Disc. AE
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Impaired liver function 4%
Disc. AE
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Diarrhea all grades, 16%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Appetite lost all grades, 17%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Nausea and vomiting all grades, 22%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Hot flushes all grades, 25%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Breast tenderness all grades, 49%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Appetite lost severe, 1.3%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Nausea and vomiting severe, 1.3%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Diarrhea severe, 1.3%
Disc. AE
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Hot flushes severe, 4%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Breast tenderness severe, 7%
250 mg 3 times / day multiple, oral
Recommended
Dose: 250 mg, 3 times / day
Route: oral
Route: multiple
Dose: 250 mg, 3 times / day
Sources:
unhealthy, adult
n = 75
Health Status: unhealthy
Condition: prostate cancer
Age Group: adult
Sex: M
Population Size: 75
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​Drug as victimTox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Effects of an environmental anti-androgen on erectile function in an animal penile erection model.
2000 Apr
Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro.
2000 Feb
Prostate cancer treated by anti-androgens: is sexual function preserved? EORTC Genitourinary Group. European Organization for Research and Treatment of Cancer.
2000 Jan
Ultrastructural and quantitative immunohistochemical changes induced by nonsteroid antiandrogens on pituitary gonadotroph population of prepubertal male rats.
2001
Optimal starting time for flutamide to prevent disease flare in prostate cancer patients treated with a gonadotropin-releasing hormone agonist.
2001
[Predicting long-term survival, and the need for hormonal therapy: a meta-analysis of RTOG prostate cancer trials].
2001 Apr
Sodium-induced rise in blood pressure is suppressed by androgen receptor blockade.
2001 Apr
The effects of intrahippocampal testosterone and flutamide on spatial localization in the Morris water maze.
2001 Apr 6
Androgen-induced up-regulation of tubulin isoforms in neuroblastoma cells.
2001 Aug
Radiation and hormonal therapy for locally advanced and clinically localized prostate cancer.
2001 Aug
Antiandrogen monotherapy: a new form of treatment for patients with prostate cancer.
2001 Aug
Testosterone suppresses spermatogenesis in juvenile spermatogonial depletion (jsd ) mice.
2001 Aug
Phase III radiation therapy oncology group (RTOG) trial 86-10 of androgen deprivation adjuvant to definitive radiotherapy in locally advanced carcinoma of the prostate.
2001 Aug 1
Determination of 2-hydroxyflutamide in human plasma by high-performance liquid chromatography and its application to pharmacokinetic studies.
2001 Aug 5
Testosterone inhibits osteoclast formation stimulated by parathyroid hormone through androgen receptor.
2001 Feb 23
Testosterone protects cerebellar granule cells from oxidative stress-induced cell death through a receptor mediated mechanism.
2001 Feb 23
[Successful complete androgen blockade (CAB) therapy for prostatic cancer detected from multiple lung metastases: a case report].
2001 Jan
Hormonal regulation of appetite and body mass in patients with advanced prostate cancer treated with combined androgen blockade.
2001 Jan
An electrochemical evidence of free radicals formation from flutamide and its reactivity with endo/xenobiotics of pharmacological relevance.
2001 Jan
Lack of methemoglobinemia with flutamide.
2001 Jan
Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function.
2001 Jan
Androgen-dependent regulation of human angiotensinogen expression in KAP-hAGT transgenic mice.
2001 Jan
Nonsteroidal antiandrogens: a therapeutic option for patients with advanced prostate cancer who wish to retain sexual interest and function.
2001 Jan
Flutamide versus prednisone in patients with prostate cancer symptomatically progressing after androgen-ablative therapy: a phase III study of the European organization for research and treatment of cancer genitourinary group.
2001 Jan 1
Sexual dimorphism and aromatase in the rat retina.
2001 Jan 31
Virilization of the urogenital sinus of the tammar wallaby is not unique to 5alpha-androstane-3alpha,17beta-diol.
2001 Jul 5
Kap promoter analysis in vivo: a regulatory role for a truncated L1 repeat.
2001 Jul 5
Strain sensitivity differences in the Hershberger assay.
2001 Jul-Aug
Steroid-sensitive gene-1 is an androgen-regulated gene expressed in prostatic smooth muscle cells in vivo.
2001 Jun
Modulation of gene expression by androgen and oestrogens in the testis and prostate of the adult rat following androgen withdrawal.
2001 Jun 10
Testosterone perturbs epidermal permeability barrier homeostasis.
2001 Mar
Subset analysis of RTOG 85-31 and 86-10 indicates an advantage for long-term vs. short-term adjuvant hormones for patients with locally advanced nonmetastatic prostate cancer treated with radiation therapy.
2001 Mar 15
Administration of tamoxifen but not flutamide to hormonally intact, adult male rats mimics the effects of short-term gonadectomy on the catecholamine innervation of the cerebral cortex.
2001 Mar 19
Suppression of androgen action and the induction of gross abnormalities of the reproductive tract in male rats treated neonatally with diethylstilbestrol.
2001 Mar-Apr
[Complete remission of brain metastases from prostate cancer by gamma knife radiosurgery: a case report].
2001 May
Androgen-driven prostate epithelial cell proliferation and differentiation in vivo involve the regulation of p27.
2001 May
Effects of acute stanozolol treatment on puberty in female rats.
2001 May
Dissection and weighing of accessory sex glands after formalin fixation, and a 5-day assay using young mature rats are reliable and feasible in the Hershberger assay.
2001 May 11
Chemical andropause and amyloid-beta peptide.
2001 May 2
Homology modeling using multiple molecular dynamics simulations and docking studies of the human androgen receptor ligand binding domain bound to testosterone and nonsteroidal ligands.
2001 May 24
Quantification of antiandrogen effect determined by Lightcycler technology.
2001 May 28
Possible androgenic/anti-androgenic activity of the insecticide fenitrothion.
2001 May-Jun
Neonatal exposure to potent and environmental oestrogens and abnormalities of the male reproductive system in the rat: evidence for importance of the androgen-oestrogen balance and assessment of the relevance to man.
2001 May-Jun
Tamoxifen is an acute, estrogen-like, coronary vasodilator of porcine coronary arteries in vitro.
2001 Nov
Phase I/II trial evaluating combined radiotherapy and in situ gene therapy with or without hormonal therapy in the treatment of prostate cancer--a preliminary report.
2001 Nov 1
Replacement of surgical castration by GnRH-inhibition or Leydig cell ablation in the male rat Hershberger antiandrogen assay.
2001 Oct
Attenuation of vascular endothelial dysfunction by testosterone receptor blockade after trauma and hemorrhagic shock.
2001 Oct
Flutamide-induced acute hepatitis in advanced prostate cancer patients.
2001 Sep
Differential gene expression in response to methoxychlor and estradiol through ERalpha, ERbeta, and AR in reproductive tissues of female mice.
2001 Sep
Use of the probasin promoter ARR2PB to express Bax in androgen receptor-positive prostate cancer cells.
2001 Sep 5
Patents

Sample Use Guides

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
Flutamide inhibited spiggin production in vitro at a concentration as low as 10(-12) M in cultures of primed female stickleback kidney cells
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:55:42 UTC 2021
Edited
by admin
on Fri Jun 25 20:55:42 UTC 2021
Record UNII
76W6J0943E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUTAMIDE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NSC-215876
Code English
FLUTAMIDE [EP MONOGRAPH]
Common Name English
FLUTAMIDE [USAN]
Common Name English
EULEXIN
Brand Name English
FLUTAMIDE [MART.]
Common Name English
FLUTAMIDE [ORANGE BOOK]
Common Name English
FLUTAMIDE [EP]
Common Name English
SCH-13521
Code English
PROPANAMIDE, 2-METHYL-N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-
Systematic Name English
SCH 13521
Code English
.ALPHA.,.ALPHA.,.ALPHA.-TRIFLUORO-2-METHYL-4'-NITRO-M-PROPIONOTOLUIDIDE
Common Name English
FLUTAMIDE [USP-RS]
Common Name English
FLUTAMIDE [MI]
Common Name English
FLUTAMIDE [WHO-DD]
Common Name English
FLUTAMIDE [USP MONOGRAPH]
Common Name English
FLUTAMIDE [JAN]
Common Name English
FLUTAMIDE [INN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175560
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
WHO-ATC L02BB01
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
NDF-RT N0000000243
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
NCI_THESAURUS C242
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
NCI_THESAURUS C1915
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
WHO-VATC QL02BB01
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
LIVERTOX 429
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
Code System Code Type Description
WIKIPEDIA
FLUTAMIDE
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
DRUG BANK
DB00499
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
MERCK INDEX
M5508
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL806
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
RXCUI
4508
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
236-341-9
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
USP_CATALOG
1285851
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY USP-RS
CAS
13311-84-7
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
DRUG CENTRAL
1223
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
INN
3483
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
PUBCHEM
3397
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
MESH
D005485
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
IUPHAR
6943
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
FDA UNII
76W6J0943E
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
EPA CompTox
13311-84-7
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
NCI_THESAURUS
C509
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
EVMPD
SUB07756MIG
Created by admin on Fri Jun 25 20:55:42 UTC 2021 , Edited by admin on Fri Jun 25 20:55:42 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (UV)
EP
BINDER->LIGAND
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TARGET -> INHIBITOR
BINDING
Related Record Type Details
METABOLITE -> PARENT
MAJOR
URINE
METABOLITE ACTIVE -> PARENT
MAJOR
PLASMA
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC