Nilutamide

• CAT Number: R008611
• CAS Number: 63612-50-0
• Molecular Formula: C12H10F3N3O4
• Molecular Weight: 317.224
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
• InChI: InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20)
• InChIKey: XWXYUMMDTVBTOU-UHFFFAOYSA-N
• SMILES: CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C

Nilutamide is an antiandrogen medication used in the treatment of advanced-stage prostate cancer. Nilutamide blocks the androgen receptor, preventing its interaction with testosterone. Because most prostate cancer cells rely on the stimulation of the androgen receptor for growth and survival, nilutamide can prolong life in men with prostate cancer. Nilutamide is marketed under the name Nilandron in the United States and under the name Anandron in Canada. (Source: http://en.wikipedia.org/wiki/Nilutamide)

Reference

1:A highly sensitive and selective electrochemical determination of non-steroidal prostate anti-cancer drug nilutamide based on f-MWCNT in tablet and human blood serum sample. Karthik R, Sasikumar R, Chen SM, Vinoth Kumar J, Elangovan A, Muthuraj V, Muthukrishnan P, Al-Hemaid FM, Ajmal Ali M, Elshikh MS.J Colloid Interface Sci. 2017 Feb 1;487:289-296. doi: 10.1016/j.jcis.2016.10.047. Epub 2016 Oct 19. PMID: 27792936 2:Lung caught in Nilutamide treatment. Lourenço EP, Nzwalo H, Sampaio MR, Brito H.BMJ Case Rep. 2016 Sep 6;2016. pii: bcr2016216590. doi: 10.1136/bcr-2016-216590. No abstract available. PMID: 27599808 3:19F Nuclear Magnetic Resonance Spectrometric Determination of the Partition Coefficients of Flutamide and Nilutamide (Antiprostate Cancer Drugs) in a Lipid Nano-Emulsion and Prediction of Its Encapsulation Efficiency for the Drugs. Takegami S, Kitamura K, Ohsugi M, Konishi A, Kitade T.AAPS PharmSciTech. 2016 Dec;17(6):1500-1506. Epub 2016 Feb 10. PMID: 26863891 4:Liquid chromatography electrospray ionization tandem mass spectrometry study of nilutamide and its stress degradation products: in silico toxicity prediction of degradation products. Ramesh Babu A, Borkar RM, Raju G, Raju B, Srinivas R.Biomed Chromatogr. 2014 Jun;28(6):788-93. doi: 10.1002/bmc.3119. PMID: 24861745 5:Nilutamide. Trasi NS, Fanwick PE, Taylor LS.Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o591. doi: 10.1107/S1600536812003728. Epub 2012 Feb 4. PMID: 22412506 Free PMC Article6:Fulminant hepatic failure due to nilutamide hepatotoxicity. Merwat SN, Kabbani W, Adler DG.Dig Dis Sci. 2009 Apr;54(4):910-3. doi: 10.1007/s10620-008-0406-8. Epub 2008 Aug 8. No abstract available. PMID: 18688719 7:Analysis of overall survival in patients with nonmetastatic castration-resistant prostate cancer treated with vaccine, nilutamide, and combination therapy. Madan RA, Gulley JL, Schlom J, Steinberg SM, Liewehr DJ, Dahut WL, Arlen PM.Clin Cancer Res. 2008 Jul 15;14(14):4526-31. doi: 10.1158/1078-0432.CCR-07-5048. PMID: 18628467 Free PMC Article8:Delayed dark adaptation caused by nilutamide. Chan P, Odel JG.J Neuroophthalmol. 2008 Jun;28(2):158-9. doi: 10.1097/WNO.0b013e3181772b5f. No abstract available. PMID: 18562852 9:Synthesis and structure-activity relationships of the first ferrocenyl-aryl-hydantoin derivatives of the nonsteroidal antiandrogen nilutamide. Payen O, Top S, Vessières A, Brulé E, Plamont MA, McGlinchey MJ, Müller-Bunz H, Jaouen G.J Med Chem. 2008 Mar 27;51(6):1791-9. doi: 10.1021/jm701264d. Epub 2008 Feb 28. PMID: 18303829 10:Metabolism of nilutamide in rat lung. Ask K, Décologne N, Ginies C, Låg M, Boucher JL, Holme JA, Pelczar H, Camus P.Biochem Pharmacol. 2006 Jan 12;71(3):377-85. Epub 2005 Nov 28. PMID: 16313887