Enzalutamide Basic information
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Product Name: |
Enzalutamide |
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Synonyms: |
4-{3-[4-cyano-3-(trifluoroMethyl)phenyl]-5,5-diMethyl-4-oxo-2-sulfanylideneiMidazolidin-1-yl}-2-fluoro-N-MethylbenzaMide;EnzalutaMide;MDV3100 (EnzalutaMide);ENZALUTAMIDE;MDV-3100;MDV-3100;4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl]-2-fluoro-N-methylbenzamide;4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide;MDV 3100,4-[3-[4-Cyano-3-(trifluoroMethyl)phenyl]-5,5-diMethyl-4-oxo-2-thioxo-1-iMidazolidinyl]-2-fluoro-N-MethylbenzaMide |
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CAS: |
915087-33-1 |
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MF: |
C21H16F4N4O2S |
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MW: |
464.44 |
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EINECS: |
805-022-1 |
Enzalutamide Chemical Properties
| Melting point | 198 - 200°C |
| density | 1.49 |
| storage temp. | -20°C |
| solubility | Soluble in DMSO (>25 mg/ml) |
| form | solid |
| pka | 13.88±0.46(Predicted) |
| color | White to off-white |
| Stability | Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
Enzalutamide Usage And Synthesis
| Description | In August 2012, the US FDA approved enzalutamide for the treatment of metastatic castration-resistant prostate cancer (mCRPC) in patients who have previously been treated with docetaxel. Synthesis of enzalutamide was achieved by a triply convergent route that employed a Strecker condensation, followed by isothiocyanate condensation and hydrolysis to form the thiohydantoin moiety. In LNCaP/AR cells with high expression of AR, enzalutamide demonstrated potent inhibition of 16b-[18F]-5α-dihydrotestosterone binding (IC50=21 nM compared with bicalutamide IC50=160 nM), and inhibited AR translocation to the nucleus more potently than bicalutamide.The primary metabolite is the result of CYP2C8-mediated N-demethylation; enzalutamide is primarily eliminated by hepatic metabolism. |
| Chemical Properties | White Solid |
| Uses |
MDV 3100 is an androgen-receptor antagonist that blocks androgens from binding to the androgen receptor and prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex. MDV 3100 has also been shown to induce tumor cell apoptosis, and has no agonist activity. MDV 3100 is a candidate for the treatment of castration-resistant prostate cancer. MDV3100, known as Enzalutamide, is a second-generation androgen receptor (AR) signaling inhibitor. It is able to inhibit binding of androgens to the AR, AR nuclear translocation, and the association of the AR with DNA. MDV 3100 is an androgen-receptor antagonist that blocks androgens from binding to the androgen receptor and prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex. MDV 3100 has also been shown to induce tumor cell apoptosis, and has no agonist activity. MDV 3100 is a candidate for the treatment of castration-resistant prostate cancer. |
It is an androgen receptor inhibitor. Its target is different from cabazitaxel and abiraterone. It can competitively inhibit the binding of androgen to the receptor and inhibit the nuclear transport of the androgen receptor. As well as the interaction between the receptor and DNA, in vitro experimental studies have shown that it can inhibit the proliferation of prostate cancer cells and induce their death and can reduce tumor volume in mouse prostate cancer xenograft model experiments The main metabolite is N-desmethyl enzalutamide, which shows similar inhibitory activity to it in vitro. The recommended adult dose of the drug is 160 mg per day. It is quickly absorbed after taking the drug.
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