Home Fluorides 52806-53-8
52806-53-8,MFCD00563126
Catalog No.:AA003HAX
52806-53-8 | 2-Hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)-phenyl)propanamide
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Purity
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25mg
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50mg
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100mg
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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003HAX
Chemical Name:
2-Hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)-phenyl)propanamide
CAS Number:
52806-53-8
Molecular Formula:
C11H11F3N2O4
Molecular Weight:
292.2112
MDL Number:
MFCD00563126
IUPAC Name:
2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
InChI:
InChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)
InChI Key:
YPQLFJODEKMJEF-UHFFFAOYSA-N
SMILES:
O=C(C(O)(C)C)Nc1ccc(c(c1)C(F)(F)F)[N+](=O)[O-]
UNII:
31D90UKP5Y
Properties
Computed Properties
 
Complexity:
392  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
292.067g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
292.214g/mol
Monoisotopic Mass:
292.067g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
95.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2  

Synonyms
 
2-hydroxyflutamide 
hydroxyflutamide 
hydroxy-flutamide 
C11-H11-F3-N2-O4 
H1600 
C014290 
alpha, alpha, alpha-trifluoro-2-methyl-4'-nitro-m-lactotoluidide 
2-Hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide 
52771-22-9 
5394-20-7 
Sch 16423 
2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide 
Hydroxy Flutamide 
UNII-31D90UKP5Y 
CHEMBL491 
31D90UKP5Y 
2-Hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)-phenyl)propanamide 
MFCD00563126 
alpha,alpha,alpha-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide 
OH-flutamide 
OH-flutamide 
Propanamide, 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]- 
DSSTox_CID_13562 
DSSTox_RID_79084 
DSSTox_GSID_33562 
HFT 
Liproca Depot 
Propanamide, 2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)- 
SMR001227196 
CAS-52806-53-8 
Sch 16423 
Hydroxyflutamid 
2-Hydroxy-flutamide 
PC1193 
PubChem19862 
2ax6 
AC1L3MI1 
AC1Q1LI1 
2-HOF 
cid_91649 
MLS001061267 
Sch-16423 
MLS006011954 
BIDD:ER0519 
GTPL2862 
SCHEMBL3079778 
DTXSID8033562 
SCHEMBL19117358 
BDBM35909 
YPQLFJODEKMJEF-UHFFFAOYSA-N 
HMS3039A05 
Hydroxyniphtholide;Hydroxy-flutamide 
Hydroxyflutamide 
BCP12495 
Hydroxyflutamide, >=98% (HPLC) 
ZINC4655055 
ZX-AP012311 
Tox21_201204 
Tox21_303659 
Hydroxyflutamide (Hydroxyniphtholide) 
AKOS007930906 
API0007072 
MCULE-6726517919 
52806-53-8 
SB17029 
VZ32394 
NCGC00091014-01 
NCGC00091014-02 
NCGC00091014-03 
NCGC00091014-04 
NCGC00091014-06 
NCGC00257382-01 
NCGC00258756-01 
AT-10518 
2-hydroxyflutamide 
CC-29438 
EN001669 
SC-51166 
AB2000537 
AX8012995 
LS-119288 
TC-030480 
A1728 
FT-0080575 
FT-0627147 
Hydroxyniphtholide 
ST24040664 
X6072 
A11865 
A21118 
C14204 
2-Hydroxy-4'-nitro-3'-(trifluoromethyl)isobutyranilide 
Z1617901126 
2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propionamide 
2-Hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide (hydroxy flutamide) 
2-Hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-propionamide(Hydroxyflutamide) 
2-Hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide 
2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide (2-Hydroxyflutamide) 
2-HYDROXY-2-METHYL-N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)PROPANAMIDE; HYDROXYNIPHTHOLIDE 
Eulexin 
D0BC2E 
Sch-16423 
cc-376 
C11H11F3N2O4 
3-(Trifluoromethoxy)benzonitrile 
CID91649 
AR-1E2288 
Literature

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Title: Incorporation of a metabolizing system in biodetection assays for endocrine active substances.

Journal: ALTEX 20170101

Title: TBECH, 1,2-dibromo-4-(1,2 dibromoethyl) cyclohexane, alters androgen receptor regulation in response to mutations associated with prostate cancer.

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Title: Development and pre-validation of an in vitro transactivation assay for detection of (anti)androgenic potential compounds using 22Rv1/MMTV cells.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20160401

Title: Effects of primary metabolites of organophosphate flame retardants on transcriptional activity via human nuclear receptors.

Journal: Toxicology letters 20160314

Title: Hydroxyflutamide affects connexin 43 via the activation of PI3K/Akt-dependent pathway but has no effect on the crosstalk between PI3K/Akt and ERK1/2 pathways at the Raf-1 kinase level in primary rat Sertoli cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20160301

Title: The ability of the YAS and AR CALUX assays to detect the additive effects of anti-androgenic fungicide mixtures.

Journal: Toxicology letters 20160122

Title: Low dose evaluation of the antiandrogen flutamide following a Mode of Action approach.

Journal: Toxicology and applied pharmacology 20151215

Title: The brominated flame retardants TBP-AE and TBP-DBPE antagonize the chicken androgen receptor and act as potential endocrine disrupters in chicken LMH cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20151201

Title: Identification of a group of brominated flame retardants as novel androgen receptor antagonists and potential neuronal and endocrine disrupters.

Journal: Environment international 20150101

Title: Metabolomics-on-a-chip of hepatotoxicity induced by anticancer drug flutamide and Its active metabolite hydroxyflutamide using HepG2/C3a microfluidic biochips.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20130301

Title: Ligand-independent androgen receptor antagonism caused by the newly developed pesticide pyrifluquinazon (PFQ).

Journal: Reproductive toxicology (Elmsford, N.Y.) 20130101

Title: Administration of flutamide alters sperm ultrastructure, sperm plasma membrane integrity and its stability, and sperm mitochondrial oxidative capability in the boar: in vivo and in vitro approach.

Journal: Reproduction in domestic animals = Zuchthygiene 20120801

Title: Design, synthesis, and biological evaluation of nonsteroidal cycloalkane[d]isoxazole-containing androgen receptor modulators.

Journal: Journal of medicinal chemistry 20120726

Title: Does 2-hydroxyflutamide inhibit apoptosis in porcine granulosa cells? - An in vitro study.

Journal: The Journal of reproduction and development 20120101

Title: Androgen receptor coregulators NOCR1, TIF2, and ARA70 may account for the hydroxyflutamide insensitivity of prostate cancer cells.

Journal: Irish journal of medical science 20111201

Title: A novel steroidal antiandrogen targeting wild type and mutant androgen receptors.

Journal: Biochemical pharmacology 20111201

Title: Characterization of steroid hormone receptor activities in 100 hydroxylated polychlorinated biphenyls, including congeners identified in humans.

Journal: Toxicology 20111118

Title: Development of 3-substituted-androsterone derivatives as potent inhibitors of 17β-hydroxysteroid dehydrogenase type 3.

Journal: Bioorganic & medicinal chemistry 20110801

Title: Unexpected binding orientation of bulky-B-ring anti-androgens and implications for future drug targets.

Journal: Journal of medicinal chemistry 20110609

Title: Androgen receptors in the posterior bed nucleus of the stria terminalis increase neuropeptide expression and the stress-induced activation of the paraventricular nucleus of the hypothalamus.

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Title: Differential effects of a complex organochlorine mixture on the proliferation of breast cancer cell lines.

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Journal: International journal of oncology 20110301

Title: QSAR models for anti-androgenic effect--a preliminary study.

Journal: SAR and QSAR in environmental research 20110301

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Title: Modulation of androgen receptor signaling in hormonal therapy-resistant prostate cancer cell lines.

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Journal: Reproductive toxicology (Elmsford, N.Y.) 20100801

Title: Determination of 2-hydroxyflutamide in human plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS): application to a bioequivalence study on Chinese volunteers.

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Title: Systematic structure-function analysis of androgen receptor Leu701 mutants explains the properties of the prostate cancer mutant L701H.

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Title: Potent and selective steroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 7, an enzyme that catalyzes the reduction of the key hormones estrone and dihydrotestosterone.

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Title: Suppression of mutant androgen receptors by flutamide.

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Title: Design and synthesis of carborane-containing androgen receptor (AR) antagonist bearing a pyridine ring.

Journal: Bioorganic & medicinal chemistry 20080901

Title: Computationally identified novel diphenyl- and phenylpyridine androgen receptor antagonist structures.

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Title: A new prostate cancer therapeutic approach: combination of androgen ablation with COX-2 inhibitor.

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Title: Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.

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Title: Identification and optimization of a novel series of [2.2.1]-oxabicyclo imide-based androgen receptor antagonists.

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Title: PRMT2, a member of the protein arginine methyltransferase family, is a coactivator of the androgen receptor.

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Title: Transport, metabolism, and hepatotoxicity of flutamide, drug-drug interaction with acetaminophen involving phase I and phase II metabolites.

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Title: Effects of steroidal and non-steroidal antiandrogens on wild-type and mutant androgen receptors.

Journal: The Prostate 20070601

Title: Dihydrotestosterone inhibits tumor necrosis factor alpha induced interleukin-1alpha mRNA expression in rheumatoid fibroblast-like synovial cells.

Journal: Biological & pharmaceutical bulletin 20070601

Title: Testosterone inhibits matrix metalloproteinase-1 production in human endometrial stromal cells in vitro.

Journal: Reproduction (Cambridge, England) 20070601

Title: Non-steroidal antiandrogens act as AF-1 agonists under conditions of high androgen-receptor expression.

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Title: Chemical synthesis and biological activities of 16alpha-derivatives of 5alpha-androstane-3alpha,17beta-diol as antiandrogens.

Journal: Bioorganic & medicinal chemistry 20070415

Title: Synthesis and biological evaluation of [18F]bicalutamide, 4-[76Br]bromobicalutamide, and 4-[76Br]bromo-thiobicalutamide as non-steroidal androgens for prostate cancer imaging.

Journal: Journal of medicinal chemistry 20070308

Title: Ligand-specific dynamics of the androgen receptor at its response element in living cells.

Journal: Molecular and cellular biology 20070301

Title: The androgen receptor T877A mutant recruits LXXLL and FXXLF peptides differently than wild-type androgen receptor in a time-resolved fluorescence resonance energy transfer assay.

Journal: Biochemistry 20070123

Title: Discovery of 7alpha-substituted dihydrotestosterones as androgen receptor pure antagonists and their structure-activity relationships.

Journal: Bioorganic & medicinal chemistry 20070101

Title: Regulation of A Disintegrin And Metalloproteinase with ThromboSpondin repeats-1 expression in human endometrial stromal cells by gonadal steroids involves progestins, androgens, and estrogens.

Journal: The Journal of clinical endocrinology and metabolism 20061201

Title: Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.

Journal: Journal of molecular graphics & modelling 20061101

Title: Anti-progestogenic effect of flutamide on uterine expression of calbindin-D9k mRNA and protein in immature mice.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20061101

Title: Chiral dimethylamine flutamide derivatives--modeling, synthesis, androgen receptor affinities and carbon-11 labeling.

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Title: Synthesis and biological evaluation of a nonsteroidal bromine-76-labeled androgen receptor ligand 3-[76Br]bromo-hydroxyflutamide.

Journal: Nuclear medicine and biology 20060801

Title: Flutamide metabolism in four different species in vitro and identification of flutamide metabolites in human patient urine by high performance liquid chromatography/tandem mass spectrometry.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20060601

Title: Androgen effects on hippocampal CA1 spine synapse numbers are retained in Tfm male rats with defective androgen receptors.

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Title: Co-activator and co-repressor interplay on the human androgen receptor.

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Title: Prostate cancer PET bioprobes: synthesis of [18F]-radiolabeled hydroxyflutamide derivatives.

Journal: Bioorganic & medicinal chemistry 20051115

Title: Androgens augment the mitogenic effects of oocyte-secreted factors and growth differentiation factor 9 on porcine granulosa cells.

Journal: Biology of reproduction 20051001

Title: Antiandrogens prevent stable DNA-binding of the androgen receptor.

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Title: The structural basis of androgen receptor activation: intramolecular and intermolecular amino-carboxy interactions.

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Title: The effects of the reported active metabolite of methoxychlor, 2,2-bis(p-hydroxyphenyl)-1,1,1-trichloroethane, on testosterone formation by cultured Leydig cells from young adult rats.

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Title: Functional domain and motif analyses of androgen receptor coregulator ARA70 and its differential expression in prostate cancer.

Journal: The Journal of biological chemistry 20040806

Title: Interactions between androgen and growth factors in granulosa cell subtypes of porcine antral follicles.

Journal: Biology of reproduction 20040701

Title: Differential effect of small ubiquitin-like modifier (SUMO)-ylation of the androgen receptor in the control of cooperativity on selective versus canonical response elements.

Journal: Molecular endocrinology (Baltimore, Md.) 20040601

Title: Evidence that inhibited prostatic epithelial bud formation in 2,3,7,8-tetrachlorodibenzo-p-dioxin-exposed C57BL/6J fetal mice is not due to interruption of androgen signaling in the urogenital sinus.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20040601

Title: Androgen receptor blockade in the MPOA or VMN: effects on male sociosexual behaviors.

Journal: Physiology & behavior 20040601

Title: Effect of organochlorine pesticides on human androgen receptor activation in vitro.

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Title: Androgen inhibition of MAP kinase pathway and Elk-1 activation in proliferating osteoblasts.

Journal: Journal of molecular endocrinology 20040201

Title: Screening of some anti-androgenic endocrine disruptors using a recombinant cell-based in vitro bioassay.

Journal: The Journal of steroid biochemistry and molecular biology 20040201

Title: Proteasome inhibitors and their combination with antiandrogens: effects on apoptosis, cellular proliferation and viability of prostatic adenocarcinoma cell cultures.

Journal: Prostate cancer and prostatic diseases 20040101

Title: Potential action of androstenedione on the proliferation and apoptosis of stromal endometrial cells.

Journal: Reproductive biology and endocrinology : RB&E 20040101

Title: Androgen dependent regulation of bacillus Calmette-Guerin induced interleukin-6 expression in human transitional carcinoma cell lines.

Journal: The Journal of urology 20031101

Title: Modulation of androgen receptor transactivation by gelsolin: a newly identified androgen receptor coregulator.

Journal: Cancer research 20030815

Title: UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20030701

Title: Inhibition of fatty acid synthase expression by 1alpha,25-dihydroxyvitamin D3 in prostate cancer cells.

Journal: The Journal of steroid biochemistry and molecular biology 20030501

Title: Effects of hydroxyflutamide in the medial preoptic area or lateral septum on reproductive behaviors in male rats.

Journal: Brain research bulletin 20021130

Title: Activation of mitogen-activated protein kinase pathway by the antiandrogen hydroxyflutamide in androgen receptor-negative prostate cancer cells.

Journal: Cancer research 20021101

Title: Nerve growth factor induces the re-expression of functional androgen receptors and p75(NGFR) in the androgen-insensitive prostate cancer cell line DU145.

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Title: Pure antiandrogens disrupt the recruitment of coactivator GRIP1 to colocalize with androgen receptor in nuclei.

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Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020701

Title: Stabilization of androgen receptor protein is induced by agonist, not by antagonists.

Journal: Biochemical and biophysical research communications 20020621

Title: Androgens protect against apolipoprotein E4-induced cognitive deficits.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20020615

Title: Cytotoxicity of flutamide and 2-hydroxyflutamide and their effects on CYP1A2 mRNA in primary rat hepatocytes.

Journal: Acta pharmacologica Sinica 20020601

Title: The amino terminus of the human AR is target for corepressor action and antihormone agonism.

Journal: Molecular endocrinology (Baltimore, Md.) 20020401

Title: A novel cell line, MDA-kb2, that stably expresses an androgen- and glucocorticoid-responsive reporter for the detection of hormone receptor agonists and antagonists.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20020301

Title: Development of two androgen receptor assays using adenoviral transduction of MMTV-luc reporter and/or hAR for endocrine screening.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20020301

Title: Role of cadmium in the regulation of AR gene expression and activity.

Journal: Endocrinology 20020101

Title: Use of the probasin promoter ARR2PB to express Bax in androgen receptor-positive prostate cancer cells.

Journal: Journal of the National Cancer Institute 20010905

Title: Determination of 2-hydroxyflutamide in human plasma by high-performance liquid chromatography and its application to pharmacokinetic studies.

Journal: Journal of chromatography. B, Biomedical sciences and applications 20010805

Title: The subnuclear three-dimensional image analysis of androgen receptor fused to green fluorescence protein.

Journal: The Journal of biological chemistry 20010727

Title: Homology modeling using multiple molecular dynamics simulations and docking studies of the human androgen receptor ligand binding domain bound to testosterone and nonsteroidal ligands.

Journal: Journal of medicinal chemistry 20010524

Title: Dexamethasone blocks antioestrogen- and oxidant-induced death of pituitary tumour cells.

Journal: The Journal of endocrinology 20010501

Title: Testosterone inhibits osteoclast formation stimulated by parathyroid hormone through androgen receptor.

Journal: FEBS letters 20010223

Title: Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function.

Journal: Molecular endocrinology (Baltimore, Md.) 20010101

Title: Androgen-induced cell growth and c-myc expression in human non-transformed epithelial prostatic cells in primary culture.

Journal: Endocrine research 20010101

Title: Regulation of GCDFP-15 expression in human mammary cancer cells.

Journal: International journal of molecular medicine 19990801

Title: Rapid and sensitive reporter gene assays for detection of antiandrogenic and estrogenic effects of environmental chemicals.

Journal: Toxicology and applied pharmacology 19990301

Title: Inhibition of androgen receptor-dependent transcriptional activity by DDT isomers and methoxychlor in HepG2 human hepatoma cells.

Journal: Toxicology and applied pharmacology 19980701

Title: Androgen antagonistic effect of estramustine phosphate (EMP) metabolites on wild-type and mutated androgen receptor.

Journal: Biochemical pharmacology 19980501

Title: Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2-dihydropyridono[5,6-g]quinolines.

Journal: Journal of medicinal chemistry 19980212

Title: Comparison of in vitro effects of the pure antiandrogens OH-flutamide, Casodex, and nilutamide on androgen-sensitive parameters.

Journal: Urology 19970401

Title: Evaluation of chemicals with endocrine modulating activity in a yeast-based steroid hormone receptor gene transcription assay.

Journal: Toxicology and applied pharmacology 19970301

Title: Non-steroidal L-245,976 acts as a classical antiandrogen in vitro.

Journal: The Journal of steroid biochemistry and molecular biology 19970101

Title: The pharmacokinetics of flutamide and its major metabolites after a single oral dose and during chronic treatment.

Journal: European journal of clinical pharmacology 19880101

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