Flutamide
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. (NCI04). Flutamide has been linked to numerous cases of acute liver injury, which are frequently severe and can be fatal.
General
Type : Trifluoro
Chemical_Nomenclature : 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Canonical SMILES : CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F
InChI : 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
Other name(s) : Eulexin || Niftolide || Niftholide
MW : 276.21
Formula : C11H11F3N2O3
CAS_number : 13311-84-7
PubChem : 3397
UniChem : MKXKFYHWDHIYRV-UHFFFAOYSA-N
Target
Structures : No structure
Families : Arylacetamide_deacetylase
References (4)
| Title : Contributions of arylacetamide deacetylase and carboxylesterase 2 to flutamide hydrolysis in human liver - Kobayashi_2012_Drug.Metab.Dispos_40_1080 |
| Author(s) : Kobayashi Y , Fukami T , Shimizu M , Nakajima M , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 40 :1080 , 2012 |
| Abstract : |
| PubMedSearch : Kobayashi_2012_Drug.Metab.Dispos_40_1080 |
| PubMedID: 22446520 |
| Title : Human arylacetamide deacetylase is a principal enzyme in flutamide hydrolysis - Watanabe_2009_Drug.Metab.Dispos_37_1513 |
| Author(s) : Watanabe A , Fukami T , Nakajima M , Takamiya M , Aoki Y , Yokoi T |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 37 :1513 , 2009 |
| Abstract : |
| PubMedSearch : Watanabe_2009_Drug.Metab.Dispos_37_1513 |
| PubMedID: 19339378 |
| Gene_locus related to this paper: human-AADAC |
| Title : Detection of a new N-oxidized metabolite of flutamide, N-[4-nitro-3-(trifluoromethyl)phenyl]hydroxylamine, in human liver microsomes and urine of prostate cancer patients - Goda_2006_Drug.Metab.Dispos_34_828 |
| Author(s) : Goda R , Nagai D , Akiyama Y , Nishikawa K , Ikemoto I , Aizawa Y , Nagata K , Yamazoe Y |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 34 :828 , 2006 |
| Abstract : |
| PubMedSearch : Goda_2006_Drug.Metab.Dispos_34_828 |
| PubMedID: 16507648 |
| Title : [Changes in liver function induced by flutamide in patients with prostate cancer (studies in patients treated with total androgen blockage)] - Ikemoto_2000_Nihon.Hinyokika.Gakkai.Zasshi_91_556 |
| Author(s) : Ikemoto I , Ohishi Y , Yamazaki H , Wada T , Aizawa Y |
| Ref : Nihon Hinyokika Gakkai Zasshi , 91 :556 , 2000 |
| Abstract : |
| PubMedSearch : Ikemoto_2000_Nihon.Hinyokika.Gakkai.Zasshi_91_556 |
| PubMedID: 10897581 |