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Details

Stereochemistry ACHIRAL
Molecular Formula C11H11F3N2O4
Molecular Weight 292.2117
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROXYFLUTAMIDE

SMILES

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

InChI

InChIKey=YPQLFJODEKMJEF-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C11H11F3N2O4
Molecular Weight 292.2117
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Hydroxyflutamide is the major active metabolite of flutamide. Flutamide undergoes extensive first-pass metabolism by CYP1A2 to its metabolite hydroxyflutamide and its hydrolysis product, 3-trifluoromethyl-4-nitroaniline. Hydroxyflutamide is a more powerful antiandrogen in vivo, with higher affinity for the receptor than that of flutamide. Hydroxyflutamide is in phase II clinical trials for the treatment of prostate cancer. However, a drug resistance problem appears after about one year's treatment. Per-residue free energy decomposition analyses indicate that N705, T877, and M895 androgen receptor mutations are vital residues in the agonist/antagonist mechanism of hydroxyflutamide.

Approval Year

Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Regulation of GCDFP-15 expression in human mammary cancer cells.
1999 Aug
Role of cadmium in the regulation of AR gene expression and activity.
2002 Jan
Acquisition of agonistic properties of nonsteroidal antiandrogens after treatment with oncostatin M in prostate cancer cells.
2002 Jul
Development of two androgen receptor assays using adenoviral transduction of MMTV-luc reporter and/or hAR for endocrine screening.
2002 Mar
A novel cell line, MDA-kb2, that stably expresses an androgen- and glucocorticoid-responsive reporter for the detection of hormone receptor agonists and antagonists.
2002 Mar
UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay.
2003 Jul
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.
2004 Jun
The structural basis of androgen receptor activation: intramolecular and intermolecular amino-carboxy interactions.
2005 Jul 12
Synthesis and biological evaluation of a nonsteroidal bromine-76-labeled androgen receptor ligand 3-[76Br]bromo-hydroxyflutamide.
2006 Aug
Regulation of A Disintegrin And Metalloproteinase with ThromboSpondin repeats-1 expression in human endometrial stromal cells by gonadal steroids involves progestins, androgens, and estrogens.
2006 Dec
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
1,1-dichloro-2,2-bis(p-chlorophenyl)ethylene (p,p'-DDE) disrupts the estrogen-androgen balance regulating the growth of hormone-dependent breast cancer cells.
2008
Screening of 397 chemicals and development of a quantitative structure--activity relationship model for androgen receptor antagonism.
2008 Apr
Differential effects of a complex organochlorine mixture on the proliferation of breast cancer cell lines.
2011 Apr
Unexpected binding orientation of bulky-B-ring anti-androgens and implications for future drug targets.
2011 Jun 9
Characterization of steroid hormone receptor activities in 100 hydroxylated polychlorinated biphenyls, including congeners identified in humans.
2011 Nov 18
Ligand-independent androgen receptor antagonism caused by the newly developed pesticide pyrifluquinazon (PFQ).
2013 Jan
Metabolomics-on-a-chip of hepatotoxicity induced by anticancer drug flutamide and Its active metabolite hydroxyflutamide using HepG2/C3a microfluidic biochips.
2013 Mar
The brominated flame retardants TBP-AE and TBP-DBPE antagonize the chicken androgen receptor and act as potential endocrine disrupters in chicken LMH cells.
2015 Dec
Low dose evaluation of the antiandrogen flutamide following a Mode of Action approach.
2015 Dec 15
Patents

Sample Use Guides

Single injection in one lobe of 2-8 mL ready-made paste (corresponding to 400-1600 mg 2-Hydroxyflutamid)
Route of Administration: Other
The dihydrotestosterone-mediated induction of Amyloid precursor protein (APP) mRNA expression was potently suppressed by 10 uM of an androgen receptor blocker hydroxyflutamide (0.35-fold and P<0.01, compared to a group treated by DHT alone), whereas hydroxyflutamide alone did not significantly alter APP mRNA level in MCF-7cells (0.79-fold, P=0.69).
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:19:22 UTC 2021
Edited
by admin
on Fri Jun 25 23:19:22 UTC 2021
Record UNII
31D90UKP5Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDROXYFLUTAMIDE
Common Name English
2-HYDROXY-2-METHYL-N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)PROPANAMIDE
Systematic Name English
3-(TRIFLUOROMETHOXY)BENZONITRILE
Systematic Name English
PROPANAMIDE, 2-HYDROXY-2-METHYL-N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-
Systematic Name English
2-HYDROXYFLUTAMIDE
Common Name English
HYDROXY-FLUTAMIDE
Common Name English
.ALPHA.-HYDROXYFLUTAMIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C146993
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
Code System Code Type Description
CAS
52806-53-8
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
PRIMARY
NCI_THESAURUS
C63948
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
PRIMARY
FDA UNII
31D90UKP5Y
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
PRIMARY
PUBCHEM
91649
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
PRIMARY
MESH
C014290
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
PRIMARY
WIKIPEDIA
Hydroxyflutamide
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
PRIMARY
EPA CompTox
52806-53-8
Created by admin on Fri Jun 25 23:19:23 UTC 2021 , Edited by admin on Fri Jun 25 23:19:23 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
Related Record Type Details
PARENT -> METABOLITE ACTIVE
MAJOR
PLASMA