Flutamide

• CAT Number: A001038
• CAS Number: 13311-84-7
• Molecular Formula: C11H11F3N2O3
• Molecular Weight: 276.2
• Purity: ≥95%
• Target: Androgen Receptor
• Solubility: >12.5mg/mL in DMSO
• Storage: -20°C
• InChI: 1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17)
• InChIKey: MKXKFYHWDHIYRV-UHFFFAOYSA-N
• SMILES: CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F

Flutamide, also known as SCH13521, is a toluidine derivative and nonsteroidal antiandrogen that is structurally related to bicalutamide and nilutamide. Flutamide and its more potent active metabolite 2-hydroxyflutamide competitively block dihydrotestosterone binding at androgen receptors, forming inactive complexes which cannot translocate into the cell nucleus. Formation of inactive receptors inhibits androgen-dependent DNA and protein synthesis, resulting in tumor cell growth arrest or transient tumor regression. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Reference

1: Pedro-Hernandez LD, Martinez Klimova E, Martinez-Klimov ME, Cortez-Maya S,
Vargas-Medina AC, Ramirez-Apan T, Hernandez-Ortega S, Martínez-Garcia M.
Anticancer Activity of Resorcinarene-PAMAM-Dendrimer Conjugates of Flutamide.
Anticancer Agents Med Chem. 2017 Dec 18. doi: 10.2174/1871520618666171219114532.
[Epub ahead of print] PubMed PMID: 29256355.

2: Correction to: Fulghesu et al., Very low dose of flutamide in the treatment of
hyperandrogenism. Gynecol Endocrinol. 2017 Nov 24:1. doi:
10.1080/09513590.2017.1408266. [Epub ahead of print] PubMed PMID: 29171313.

3: Fulghesu AM, Melis F, Murru G, Canu E, Melis GB. Very low dose of flutamide in
the treatment of hyperandrogenism. Gynecol Endocrinol. 2017 Nov 6:1-5. doi:
10.1080/09513590.2017.1397114. [Epub ahead of print] PubMed PMID: 29108453.

4: Lee KH. Expressional Changes of Connexin Isoform Genes in the Rat Caput
Epididymis Exposed to Flutamide or Estradiol Benzoate at the Early Postnatal Age.
Dev Reprod. 2017 Sep;21(3):317-325. doi: 10.12717/DR.2017.21.3.317. Epub 2017 Sep
30. PubMed PMID: 29082347; PubMed Central PMCID: PMC5651698.

5: Czaja E, Wieciech-Rojkiewicz I, Knapczyk-Stwora K, Grzesiak M, Slomczynska M.
The impact of antiandrogen flutamide on the hypoxia inducible factor 1a and
vascular endothelial growth factor A gene and protein expression in the pig
placenta during late pregnancy. Folia Histochem Cytobiol. 2017;55(3):159-167.
doi: 10.5603/FHC.a2017.0018. Epub 2017 Oct 10. PubMed PMID: 28994098.

6: Chmiel K, Knapik-Kowalczuk J, Jurkiewicz K, Sawicki W, Jachowicz R, Paluch M.
A New Method To Identify Physically Stable Concentration of Amorphous Solid
Dispersions (I): Case of Flutamide + Kollidon VA64. Mol Pharm. 2017 Oct
2;14(10):3370-3380. doi: 10.1021/acs.molpharmaceut.7b00382. Epub 2017 Sep 7.
PubMed PMID: 28787567.

7: Tian J, Liu L, Han Y, Yang Y, Jin S, Yang J. Effects of testosterone and
flutamide on reproduction in Brachionus calyciflorus. Sci Rep. 2017 Jul
26;7(1):6569. doi: 10.1038/s41598-017-05517-4. PubMed PMID: 28747724; PubMed
Central PMCID: PMC5529538.

8: Mendoza FJ, Serrano-Rodriguez JM, Buzon-Cuevas A, Perez-Ecija A.
Pharmacokinetics of the anti-androgenic drug flutamide in healthy stallions. Vet
J. 2017 Jun;224:50-54. doi: 10.1016/j.tvjl.2017.06.001. Epub 2017 Jun 7. PubMed
PMID: 28697876.

9: Zacharia LC. Permitted Daily Exposure of the Androgen Receptor Antagonist
Flutamide. Toxicol Sci. 2017 Oct 1;159(2):279-289. doi: 10.1093/toxsci/kfx135.
PubMed PMID: 28666357.

10: Caceres S, Monsalve B, Peña L, de Andres PJ, Alonso-Diez A, Illera MJ,
Woodward WA, Reuben JM, Silvan G, Illera JC. In vitro and in vivo effect of
flutamide on steroid hormone secretion in canine and human inflammatory breast
cancer cell lines. Vet Comp Oncol. 2017 Jun 6. doi: 10.1111/vco.12324. [Epub
ahead of print] PubMed PMID: 28589573.