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H4166 Sigma

Hydroxyflutamide

≥98% (HPLC)

Synonym: 2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide, 2-Hydroxyflutamide, Hydroxyniphtholide, Sch 16423, a,a,a-Trifluoro-2-methyl-4′-nitro-m-lactotoluidide

  • CAS Number 52806-53-8

  • Empirical Formula (Hill Notation) C11H11F3N2O4

  • Molecular Weight 292.21

  •  MDL number MFCD00563126

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Properties

Related Categories Androgen, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology,
assay   ≥98% (HPLC)
form   powder
storage condition   desiccated
color   white to tan
solubility   DMSO: >10 mg/mL
originator   Schering Plough
storage temp.   room temp

Description

Biochem/physiol Actions

Hydroxflutamide is an AR antagonist. Androgen receptors (ARs) are nuclear hormone receptors/transcription factors. Hydroxyflutamide is an androgen antagonist with publications going back to 1981. It is one of a few gold standard AR antagonists; activities of new antagonists are measured against hydroxyflutamide.

Features and Benefits

This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Schering Plough. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H4166.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
Safety Statements (Europe) 
26-36/37/39
WGK Germany 
3
RTECS 
TX1466250

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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Inhibition of prostate cancer cell growth by second-site androgen receptor antagonists. Joseph, J.D., et al. Proc. Natl. Acad. Sci. U. S. A., (2009)

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Microarray coupled to quantitative RT-PCR analysis of androgen-regulated genes in human LNCaP prostate cancer cells. Ngan, S., et al. Oncogene 28, 2051-2-63, (2009)

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Functional AR signaling is evident in an in vitro mouse follicle culture bioassay that encompasses most stages of folliculogenesis. Lenie, S., et al. Biol. Reprod. 80, 685-695, (2009)

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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. Bingham B, Myung C, Innala L, et al. Biol. Psychiatry 36(7), 1433-43, (2011)

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Modulation of androgen receptor signaling in hormonal therapy-resistant prostate cancer cell lines. Marques RB, Dits NF, Erkens-Schulze S, et al. PLoS ONE 6(8), e23144, (2011)

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QSAR models for anti-androgenic effect--a preliminary study. Jensen GE, Nikolov NG, Wedebye EB, et al. SAR QSAR Environ. Res. 22(1-2), 35-49, (2011)

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Systematic structure-function analysis of androgen receptor Leu701 mutants explains the properties of the prostate cancer mutant L701H. van de Wijngaart DJ, Molier M, Lusher SJ, et al. J. Biol. Chem. 285(7), 5097-105, (2010)

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Metabolomics-on-a-chip of hepatotoxicity induced by anticancer drug flutamide and Its active metabolite hydroxyflutamide using HepG2/C3a microfluidic biochips. Choucha Snouber L, Bunescu A, Naudot M, et al. Toxicol. Sci. 132(1), 8-20, (2013)

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Androgen receptor signals regulate UDP-glucuronosyltransferases in the urinary bladder: a potential mechanism of androgen-induced bladder carcinogenesis. Izumi K, Zheng Y, Hsu JW, et al. Mol. Carcinog. 52(2), 94-102, (2013)

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Testosterone inhibits matrix metalloproteinase-1 production in human endometrial stromal cells in vitro. Ishikawa T, Harada T, Kubota T, et al. Reproduction 133(6), 1233-9, (2007)

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A novel steroidal antiandrogen targeting wild type and mutant androgen receptors. Andrieu T, Bertolini R, Nichols SE, et al. Biochem. Pharmacol. 82(11), 1651-62, (2011)

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Computationally identified novel diphenyl- and phenylpyridine androgen receptor antagonist structures. Söderholm AA, Viiliäinen J, Lehtovuori PT, et al. J. Chem. Inf. Model. 48(9), 1882-90, (2008)

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Transport, metabolism, and hepatotoxicity of flutamide, drug-drug interaction with acetaminophen involving phase I and phase II metabolites. Kostrubsky SE, Strom SC, Ellis E, et al. Chem. Res. Toxicol. 20(10), 1503-12, (2007)

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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. Lydka M, Piasecka M, Gaczarzewicz D, et al. Reprod. Domest. Anim. 47(4), 635-43, (2012)

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Suppression of androgen receptor enhances the self-renewal of mesenchymal stem cells through elevated expression of EGFR. Huang CK, Tsai MY, Luo J, et al. Biochim. Biophys. Acta 1833(5), 1222-34, (2013)

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Production of human metabolites of the anti-cancer drug flutamide via biotransformation in Cunninghamella species. Amadio J and Murphy CD Biotechnol. Lett. 33(2), 321-6, (2011)

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Does 2-hydroxyflutamide inhibit apoptosis in porcine granulosa cells? - An in vitro study. Duda M, Durlej M, Knet M, et al. J. Reprod. Dev. 58(4), 438-44, (2012)

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A new prostate cancer therapeutic approach: combination of androgen ablation with COX-2 inhibitor. Cai Y, Lee YF, Li G, et al. Int. J. Cancer 123(1), 195-201, (2008)

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A mouse model of androgenetic alopecia. Crabtree JS, Kilbourne EJ, Peano BJ, et al. Endocrinology 151(5), 2373-80, (2010)

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Suppression of mutant androgen receptors by flutamide. Ishioka J, Hara S, Isaacs JT, et al. Int. J. Urol. 16(5), 516-21, (2009)

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Hydroxyflutamide enhances cellular sensitivity to 5-fluorouracil by suppressing thymidylate synthase expression in bicalutamide-resistant human prostate cancer cells. Kawabata R, Oie S, Oka T, et al. Int. J. Oncol. 38(3), 665-76, (2011)

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Determination of 2-hydroxyflutamide in human plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS): application to a bioequivalence study on Chinese volunteers. Zheng H, Wu D, Qian ZY, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 878(19), 1611-5, (2010)

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Nandrolone decreases mu opioid receptor expression in SH-SY5Y human neuroblastoma cells. Guarino G and Spampinato S Neuroreport 19(11), 1131-5, (2008)

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Fluorescence lifetime imaging microscopy for the monitoring of green fluorescent protein-tagged androgen receptors in living cells. Miyake R, Uchimura T, Li X, et al. Chem. Pharm. Bull. 61(1), 82-4, (2013)

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Effects of testosterone and 2-hydroxyflutamide on progesterone receptor expression in porcine ovarian follicles in vitro. Duda M, Durlej-Grzesiak M, Tabarowski Z, et al. Reprod. Biol. 12(4), 333-40, (2012)

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Androgen receptor coregulators NOCR1, TIF2, and ARA70 may account for the hydroxyflutamide insensitivity of prostate cancer cells. Wang Y, Li JQ, Shao C, et al. Ir. J. Med. Sci. 180(4), 865-72, (2011)

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Is the "comb over" dying? A mouse model for male pattern baldness (androgenic alopecia). Walker WH Endocrinology 151(5), 1981-3, (2010)

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