2-Hydroxyflutamide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 529006

CAS#: 52806-53-8

Description: 2-Hydroxyflutamide is an androgen receptor antagonist potentially for the treatment of prostate cancer


Price and Availability

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2-Hydroxyflutamide is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529006
Name: 2-Hydroxyflutamide
CAS#: 52806-53-8
Chemical Formula: C11H11F3N2O4
Exact Mass: 292.0671
Molecular Weight: 292.21
Elemental Analysis: C, 45.21; H, 3.79; F, 19.50; N, 9.59; O, 21.90


Synonym: 2-HOF; 2HOF; 2 HOF;

IUPAC/Chemical Name: 2-hydroxy-2-methyl-N-(4-nitro-3-(trifluoromethyl)phenyl)propanamide

InChi Key: YPQLFJODEKMJEF-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: CC(C)(O)C(NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Ball AL, Kamalian L, Alfirevic A, Lyon JJ, Chadwick AE. Identification of the Additional Mitochondrial Liabilities of 2-Hydroxyflutamide When Compared With its Parent Compound, Flutamide in HepG2 Cells. Toxicol Sci. 2016 Oct;153(2):341-51. doi: 10.1093/toxsci/kfw126. PubMed PMID: 27413113; PubMed Central PMCID: PMC5036617.

2: Duda M, Grzesiak M, Knet M, Knapczyk-Stwora K, Tabarowski Z, Michna A, Slomczynska M. The impact of antiandrogen 2-hydroxyflutamide on the expression of steroidogenic enzymes in cultured porcine ovarian follicles. Mol Biol Rep. 2014 Jul;41(7):4213-22. doi: 10.1007/s11033-014-3291-6. PubMed PMID: 24584661; PubMed Central PMCID: PMC4066179.

3: Górowska-Wójtowicz E, Hejmej A, Kamińska A, Pardyak L, Kotula-Balak M, Dulińska-Litewka J, Laidler P, Bilińska B. Anti-androgen 2-hydroxyflutamide modulates cadherin, catenin and androgen receptor phosphorylation in androgen-sensitive LNCaP and androgen-independent PC3 prostate cancer cell lines acting via PI3K/Akt and MAPK/ERK1/2 pathways. Toxicol In Vitro. 2017 Apr;40:324-335. doi: 10.1016/j.tiv.2017.01.019. PubMed PMID: 28163245.

4: Sjögren E, Tammela TL, Lennernäs B, Taari K, Isotalo T, Malmsten LÅ, Axén N, Lennernäs H. Pharmacokinetics of an injectable modified-release 2-hydroxyflutamide formulation in the human prostate gland using a semiphysiologically based biopharmaceutical model. Mol Pharm. 2014 Sep 2;11(9):3097-111. doi: 10.1021/mp5002813. PubMed PMID: 25055161.

5: Duda M, Wolna A, Knapczyk-Stwora K, Durlej-Grzesiak M, Knet M, Tabarowski Z, Slomczynska M. The influence of the antiandrogen 2-hydroxyflutamide on the androgen receptor expression in the porcine ovarian follicles - an in vitro study. Reprod Domest Anim. 2013 Jun;48(3):454-62. doi: 10.1111/rda.12097. PubMed PMID: 23113830.

6: Zheng H, Wu D, Qian ZY, Xiang Y. Determination of 2-hydroxyflutamide in human plasma by liquid chromatography-tandem mass spectrometry (LC-MS/MS): application to a bioequivalence study on Chinese volunteers. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Jun 1;878(19):1611-5. doi: 10.1016/j.jchromb.2010.03.042. PubMed PMID: 20427247.

7: Duda M, Durlej-Grzesiak M, Tabarowski Z, Slomczynska M. Effects of testosterone and 2-hydroxyflutamide on progesterone receptor expression in porcine ovarian follicles in vitro. Reprod Biol. 2012 Dec;12(4):333-40. doi: 10.1016/j.repbio.2012.10.006. PubMed PMID: 23229004.

8: Duda M, Durlej M, Knet M, Knapczyk-Stwora K, Tabarowski Z, Slomczynska M. Does 2-hydroxyflutamide inhibit apoptosis in porcine granulosa cells? - An in vitro study. J Reprod Dev. 2012;58(4):438-44. PubMed PMID: 22522230.

9: Wang HX, Ma XC, Deng QL, Li D. Cytotoxicity of flutamide and 2-hydroxyflutamide and their effects on CYP1A2 mRNA in primary rat hepatocytes. Acta Pharmacol Sin. 2002 Jun;23(6):562-6. PubMed PMID: 12060533.

10: Niopas I, Daftsios AC. Determination of 2-hydroxyflutamide in human plasma by high-performance liquid chromatography and its application to pharmacokinetic studies. J Chromatogr B Biomed Sci Appl. 2001 Aug 5;759(1):179-83. PubMed PMID: 11499624.

11: Chojnacka K, Zarzycka M, Hejmej A, Mruk DD, Gorowska E, Kotula-Balak M, Klimek M, Bilinska B. 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. doi: 10.1016/j.tiv.2015.09.027. PubMed PMID: 26437446.

12: Xu CJ, Li D. Pharmacokinetics of 2-hydroxyflutamide, a major metabolite of flutamide, in normal and CCl4-poisoned rats. Zhongguo Yao Li Xue Bao. 1999 Jul;20(7):655-8. PubMed PMID: 10678134.

13: Xu CJ, Li D. Pharmacokinetics of flutamide and its metabolite 2-hydroxyflutamide in normal and hepatic injury rats. Zhongguo Yao Li Xue Bao. 1998 Jan;19(1):39-43. PubMed PMID: 10375756.

14: Zarzycka M, Kotwicka M, Jendraszak M, Skibinska I, Kotula-Balak M, Bilinska B. Hydroxyflutamide alters the characteristics of live boar spermatozoa. Theriogenology. 2014 Oct 15;82(7):988-96. doi: 10.1016/j.theriogenology.2014.07.013. PubMed PMID: 25129871.

15: Kostrubsky SE, Strom SC, Ellis E, Nelson SD, Mutlib AE. Transport, metabolism, and hepatotoxicity of flutamide, drug-drug interaction with acetaminophen involving phase I and phase II metabolites. Chem Res Toxicol. 2007 Oct;20(10):1503-12. PubMed PMID: 17900172.

16: Shang Z, Li Y, Zhang M, Tian J, Han R, Shyr CR, Messing E, Yeh S, Niu Y, Chang C. 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. doi: 10.1158/1535-7163.MCT-14-1055-T. PubMed PMID: 26264279; PubMed Central PMCID: PMC4704455.

17: Choucha Snouber L, Bunescu A, Naudot M, Legallais C, Brochot C, Dumas ME, Elena-Herrmann B, Leclerc E. Metabolomics-on-a-chip of hepatotoxicity induced by anticancer drug flutamide and Its active metabolite hydroxyflutamide using HepG2/C3a microfluidic biochips. Toxicol Sci. 2013 Mar;132(1):8-20. doi: 10.1093/toxsci/kfs230. PubMed PMID: 22843567.

18: Wang Y, Li JQ, Shao C, Shi CH, Liu F, Yang ZY, Qiu JX, Li YM, Fu Q, Zhang W, Xue W, Lei YH, Gao JY, Wang JY, Gao XP, Yuan JL, Bao TY, Zhang YT. Androgen receptor coregulators NOCR1, TIF2, and ARA70 may account for the hydroxyflutamide insensitivity of prostate cancer cells. Ir J Med Sci. 2011 Dec;180(4):865-72. doi: 10.1007/s11845-011-0714-4. PubMed PMID: 21748440.

19: Parent EE, Jenks C, Sharp T, Welch MJ, Katzenellenbogen JA. Synthesis and biological evaluation of a nonsteroidal bromine-76-labeled androgen receptor ligand 3-[76Br]bromo-hydroxyflutamide. Nucl Med Biol. 2006 Aug;33(6):705-13. PubMed PMID: 16934689.

20: Wang HX, Li D, Xu CJ, Liu X. [Sex-difference on flutamide metabolism in rat liver microsomal cytochrome P450 1A2]. Yao Xue Xue Bao. 2002 Aug;37(8):608-10. Chinese. PubMed PMID: 12567773.