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Hydroxyflutamide

CAT: 0804-HY-W013272-04Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W013272-04Size:25 mg
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Description
Hydroxyflutamide (HFT) is the active metabolite of Flutamide and exhibits oral activity. Hydroxyflutamide is a potent androgen receptor antagonist with an IC50 of 700 nM. Hydroxyflutamide can affect embryonic development and reproductive tract development in mice. Additionally, Hydroxyflutamide can enhance the efficacy of Bacillus Calmette-Guérin (BCG) to better inhibit the progression of bladder cancer. Hydroxyflutamide can be used in research related to tumors and reproductive diseases[1][2][3][4][5].
CAS Number
52806-53-8
Product Name Alternative
HFT
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
Akt; Androgen Receptor; Drug Metabolite; Gap Junction Protein; Integrin; PI3K
Type
Reference compound
Related Pathways
Cytoskeleton; Metabolic Enzyme/Protease; PI3K/Akt/mTOR; Vitamin D Related/Nuclear Receptor
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/hydroxyflutamide.html
Purity
99.90
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
CC(C)(O)C(NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1)=O
Molecular Formula
C11H11F3N2O4
Molecular Weight
292.21
Precautions
H315, H319, H335
References & Citations
[1]Furr BJ, et, al. Casodex: preclinical studies and controversies. Ann N Y Acad Sci. 1995 Jun 12;761:79-96. |[2]Yallampalli C, et al. Influence of the anti-androgen hydroxyflutamide on in vitro development of mouse embryos. J Reprod Fertil. 1993 Nov;99 (2) :467-70.|[3]Shang Z, et al. Antiandrogen Therapy with Hydroxyflutamide or Androgen Receptor Degradation Enhancer ASC-J9 Enhances BCG Efficacy to Better Suppress Bladder Cancer Progression. Mol Cancer Ther. 2015 Nov;14 (11) :2586-94.|[4]Chojnacka K, et al. 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. Toxicol In Vitro. 2016 Mar;31:146-57.|[5]Silversides DW, et al. Effects of short-term exposure to hydroxyflutamide in utero on the development of the reproductive tract in male mice. Can J Physiol Pharmacol. 1995 Nov;73 (11) :1582-8.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C, 3 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Hydroxyflutamide

2-hydroxyflutamide is a metabolite of flutamide. Flutamide is an oral nonsteroidal antiandrogen drug primarily used to treat prostate cancer. It competes with testosterone and its powerful metabolite, dihydrotestosterone (DHT) for binding to androgen receptors in the prostate gland. By doing so, it prevents them from stimulating the prostate cancer cells to grow. Flutamide has been largely replaced by a newer member of this class, bicalutamide, due to a better side-effect profile. (Wikipedia)

CAS Number52806-53-8
PubChem CID91649
IUPAC Name2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Molecular FormulaC11H11F3N2O4
Molecular Weight292.21
XLogP2.2
Topological Polar Surface Area95.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Heavy Atom Count20
Formal Charge0
Complexity392
SMILES
CC(C)(C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F)O
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)
InChIKey
YPQLFJODEKMJEF-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Hydroxyflutamide
CAS: 52806-53-8
CID: 91649
Formula: C11H11F3N2O4
MW: 292.21
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight292.21
XLogP32.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass292.06709132
Monoisotopic Mass292.06709132
Topological Polar Surface Area95.2 Ų
Heavy Atom Count20
Formal Charge0
Complexity392
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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GP8298-25mgHydroxyflutamide
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MBS385470-01Hydroxyflutamide (Hydroxyniphtholide)
A11865-50Hydroxyflutamide (Hydroxyniphtholide) 50mg
A11865-10Hydroxyflutamide (Hydroxyniphtholide) 10mg
A11865-5Hydroxyflutamide (Hydroxyniphtholide) 5mg
A11865-200Hydroxyflutamide (Hydroxyniphtholide) 200mg
A11865-100Hydroxyflutamide (Hydroxyniphtholide) 100mg
A11865-25Hydroxyflutamide (Hydroxyniphtholide) 25mg
A11865-10mM-DHydroxyflutamide (Hydroxyniphtholide) 10mM * 1mL in DMSO

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