FLUTAMIDE

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 Search

SMILES

CC(C)C(=O)NC1=CC=C(C(=C1)C(F)(F)F)[N+]([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	276.2118
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.drugbank.ca/drugs/DB00499
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
LNCaP 3 Target ID: CHEMBL612518 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21600678	Inhibitor 8504		0.9 µM [IC50]
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: http://www.drugbank.ca/drugs/DB00499	Antagonist 2849		102.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Metastatic carcinoma of the prostate 1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2001/18554s23lbl.pdf	Primary		Approved 8583	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 1989

C_max

Value	Dose	Analyte	Population
2.42 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3169114/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
53.4 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10073738	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
25.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2754024	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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2754024	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
1629 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/18554s23lbl.pdf	250 mg 3 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN
967 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10073738	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
24.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3169114/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1999002/	250 mg 3 times / day multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
96.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10073738	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
63 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2754024	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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2754024	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
4993 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10073738	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
13.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3169114/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FED
9.6 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2001/18554s23lbl.pdf	250 mg 3 times / day steady-state, oral dose: 250 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: MALE food status: UNKNOWN
7.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10073738	250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered:	HYDROXYFLUTAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
6% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10073738	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

Dose	Population	Adverse 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 Sources: https://pubmed.ncbi.nlm.nih.gov/18339379/	unhealthy, 26.3 Health Status: unhealthy Age Group: 26.3 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18339379/	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: https://pubmed.ncbi.nlm.nih.gov/18339379/
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: https://pubmed.ncbi.nlm.nih.gov/8977067/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/8977067/	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: https://pubmed.ncbi.nlm.nih.gov/8977067/

AEs

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5132	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5132
ChemicalBook	CB2468110	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2468110
eMolecules	538525	https://www.emolecules.com/cgi-bin/more?vid=538525
MolPort	MolPort-001-771-894	https://www.molport.com/shop/molecule-link/MolPort-001-771-894
Selleck Chemicals	Flutamide(Eulexin)	http://www.selleckchem.com/products/Flutamide(Eulexin).html
ZINC	ZINC000003812944	http://zinc15.docking.org/substances/ZINC000003812944

PubMed

Title	Date	PubMed
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.	2001-11-01	11597799
Tamoxifen is an acute, estrogen-like, coronary vasodilator of porcine coronary arteries in vitro.	2001-11	11602812
Replacement of surgical castration by GnRH-inhibition or Leydig cell ablation in the male rat Hershberger antiandrogen assay.	2001-10	11603962
Attenuation of vascular endothelial dysfunction by testosterone receptor blockade after trauma and hemorrhagic shock.	2001-10	11585509
Use of the probasin promoter ARR2PB to express Bax in androgen receptor-positive prostate cancer cells.	2001-09-05	11535706
Flutamide-induced acute hepatitis in advanced prostate cancer patients.	2001-09	11563686
Differential gene expression in response to methoxychlor and estradiol through ERalpha, ERbeta, and AR in reproductive tissues of female mice.	2001-09	11509743
Strain sensitivity differences in the Hershberger assay.	2001-08-08	11489600
Determination of 2-hydroxyflutamide in human plasma by high-performance liquid chromatography and its application to pharmacokinetic studies.	2001-08-05	11499624
Phase III radiation therapy oncology group (RTOG) trial 86-10 of androgen deprivation adjuvant to definitive radiotherapy in locally advanced carcinoma of the prostate.	2001-08-01	11483335
Androgen-induced up-regulation of tubulin isoforms in neuroblastoma cells.	2001-08	11520906
Radiation and hormonal therapy for locally advanced and clinically localized prostate cancer.	2001-08	11502455
Antiandrogen monotherapy: a new form of treatment for patients with prostate cancer.	2001-08	11502439
Testosterone suppresses spermatogenesis in juvenile spermatogonial depletion (jsd ) mice.	2001-08	11466222
Regulation of keratinocyte growth factor receptor and androgen receptor in epithelial cells of the human prostate.	2001-08	11458116
Prospective evaluation of hot flashes during treatment with parenteral estrogen or complete androgen ablation for metastatic carcinoma of the prostate.	2001-08	11458057
Randomized comparative study of 3 versus 8-month neoadjuvant hormonal therapy before radical prostatectomy: biochemical and pathological effects.	2001-08	11458055
Androgen-mediated development in male rat offspring exposed to flutamide in utero: permanence and correlation of early postnatal changes in anogenital distance and nipple retention with malformations in androgen-dependent tissues.	2001-08	11452136
The subnuclear three-dimensional image analysis of androgen receptor fused to green fluorescence protein.	2001-07-27	11369770
Virilization of the urogenital sinus of the tammar wallaby is not unique to 5alpha-androstane-3alpha,17beta-diol.	2001-07-05	11476945
Kap promoter analysis in vivo: a regulatory role for a truncated L1 repeat.	2001-07-05	11476941
M1 prostate cancer with a serum level of prostate-specific antigen less than 10 ng/mL.	2001-07	11442659
Testosterone inhibits spermatogonial differentiation in juvenile spermatogonial depletion mice.	2001-07	11415997
Androgen-induced cell growth and c-myc expression in human non-transformed epithelial prostatic cells in primary culture.	2001-06-29	11428707
Possible androgenic/anti-androgenic activity of the insecticide fenitrothion.	2001-06-19	11404828
Why phase III trials of maximal androgen blockade versus castration in M1 prostate cancer rarely show statistically significant differences.	2001-06-15	11391684
Modulation of gene expression by androgen and oestrogens in the testis and prostate of the adult rat following androgen withdrawal.	2001-06-10	11403897
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.	2001-06-08	11392370
Actions of the endocrine disruptor methoxychlor and its estrogenic metabolite on in vitro embryonic rat seminiferous cord formation and perinatal testis growth.	2001-06-08	11390175
Testosterone-mediated neuroprotection through the androgen receptor in human primary neurons.	2001-06	11389183
Sex differences in infant rhesus macaque separation-rejection vocalizations and effects of prenatal androgens.	2001-06	11374912
Developmental and hormonal regulation of type II DNA topoisomerase in rat testis.	2001-06	11357056
Steroid-sensitive gene-1 is an androgen-regulated gene expressed in prostatic smooth muscle cells in vivo.	2001-06	11357054
Quantification of antiandrogen effect determined by Lightcycler technology.	2001-05-28	11376863
Homology modeling using multiple molecular dynamics simulations and docking studies of the human androgen receptor ligand binding domain bound to testosterone and nonsteroidal ligands.	2001-05-24	11356108
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.	2001-05-11	11337110
Initial induction and subsequent reduction of alpha(2u)-globulin in urine and serum of mature male rats after repeated intraperitoneal injections of (anti)estrogen.	2001-05-11	11337107
Chemical andropause and amyloid-beta peptide.	2001-05-02	11325319
[Complete remission of brain metastases from prostate cancer by gamma knife radiosurgery: a case report].	2001-05	11433755
A novel isoform of human fibroblast growth factor 8 is induced by androgens and associated with progression of esophageal carcinoma.	2001-05	11341643
Androgen-driven prostate epithelial cell proliferation and differentiation in vivo involve the regulation of p27.	2001-05	11328857
Appropriate column configurations for the rapid analysis and semipreparative purification of the radiolabeled drug flutamide by high-performance liquid chromatography.	2001-04-20	11358217
[What is the role of hormonal treatments in acne?].	2001-04	11450396
[Clinical efficacy of treatment with low-dose flutamide in maximum androgen blockade therapy].	2001-04	11411099
[Predicting long-term survival, and the need for hormonal therapy: a meta-analysis of RTOG prostate cancer trials].	2001-04	11355590
Feasibility and potential gains of enhancing the subacute rat study protocol (OECD test guideline no. 407) by additional parameters selected to determine endocrine modulation. A pre-validation study to determine endocrine-mediated effects of the antiandrogenic drug flutamide.	2001-04	11354908
[Hirsutism, flutamide and hepatotoxicity].	2001-04	11333662
[Anemia and neoadjuvant hormone therapy in radical surgery of localized cancer of the prostate].	2001-02	11345792
Ultrastructural and quantitative immunohistochemical changes induced by nonsteroid antiandrogens on pituitary gonadotroph population of prepubertal male rats.	2001	11340263
A risk-benefit assessment of pharmacological therapies for hirsutism.	2001	11330656

Patents

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

Substance Class	Chemical Created by `admin` on `Wed Apr 02 09:29:25 GMT 2025` Edited by `admin` on `Wed Apr 02 09:29:25 GMT 2025`
Record UNII	76W6J0943E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EULEXIN

Preferred Name

English

FLUTAMIDE

Official Name

English

NSC-215876

Code

English

FLUTAMIDE [EP IMPURITY]

Common Name

English

FLUTAMIDE [EP MONOGRAPH]

Common Name

English

FLUTAMIDE [USAN]

Common Name

English

FLUTAMIDE [MART.]

Common Name

English

FLUTAMIDE [ORANGE BOOK]

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