Enzalutamide (MDV3100)
Enzalutamide (MDV3100) structure
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Common Name | Enzalutamide (MDV3100) | ||
|---|---|---|---|---|
| CAS Number | 915087-33-1 | Molecular Weight | 464.436 | |
| Density | 1.5±0.1 g/cm3 | Boiling Point | N/A | |
| Molecular Formula | C21H16F4N4O2S | Melting Point | N/A | |
| MSDS | N/A | Flash Point | N/A | |
Use of Enzalutamide (MDV3100)Enzalutamide (MDV3100) is an androgen receptor (AR) antagonist with an IC50 of 36 nM in LNCaP prostate cells. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | enzalutamide |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | Enzalutamide (MDV3100) is an androgen receptor (AR) antagonist with an IC50 of 36 nM in LNCaP prostate cells. |
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| Related Catalog | |
| Target |
IC50: 36 nM (androgen-receptor, in LNCaP cells)[1] |
| In Vitro | Enzalutamide has greater affinity to AR than Bicalutamide does in a competition assay with 16β-[18F]fluoro-5α-DHT (18-FDHT) in castration-resistant LNCaP/AR cells (AR-overexpressing). While Enzalutamide shows no agonism in LNCaP/AR prostate cells. Enzalutamide antagonizes induction of prostate-specific antigen (PSA) and transmembrane serine protease 2 (TMPRSS2), combination with the synthetic androgen R1881 in parental LNCaP cells. Enzalutamide inhibits the transcriptional activity of a mutant AR protein (W741C, mutation of Trp741 to Cys)[1]. Enzalutamide also prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex[2]. |
| In Vivo | Enzalutamide induces great tumor regression in castrate male mice bearing LNCaP/AR xenografts at a dose of 10 mg/kg[1]. Enzalutamide shows dose-independent pharmacokinetics at intravenous and oral doses of 0.5-5 mg/kg[4]. |
| Cell Assay | LNCaP cells (107 cells/condition) are grown in RPMI media supplemented with 5% charcoalstripped serum for 22 days, then treated with DMSO or 1 nM R1881, combined with an antiandrogen (DMSO, 1 μM Bicalutamide, 10 μM Bicalutamide, 1 μM RD162, 10 μM RD162, 1 μM MDV3100, or 10 μM MDV3100) for 8 hours. An aliquot of cells are harvested for qRT-PCR of PSA and TMPRSS2 mRNA. The remaining cells are cross-linked using 1% paraformaldehyde for 10 minutes, then glycine is added and samples centrifuged (4°C, 4000 rpm, 5 minutes) to stop further crosslinking. Chromatin immunoprecipitation is performed using a chromatin immunoprecipitation assay kit. Immunoprecipitated DNA is amplified by real-time PCR. Primers are PSA enhancer forward-ATGTTCACATTAGTACACCTTGCC and reverse-TCTCAGATCCAGGCTTGCTTACTGTC and TMPRSS2 enhancer forward-TGGTCCTGGATGATAAAAAAAGTTT and reverse-GACATACGCCCCACAACAGA[1]. |
| Animal Admin | Mice[3] Following a 5-day acclimation period, 5- to 9-week-old male CB17SCID mice are castrated and allowed to recover for an additional 5 days before inoculation with tumor cells. LNCaP cells co-expressing exogenous AR and the AR-dependent reporter construct ARR2-Pb-Luc (LNCaP-AR-Lux cells) are used to generate a xenograft model of human prostate cancer. Before implantation, LNCaP-AR-Lux cells are prepared by the addition of trypsin-EDTA, washed with complete medium, collected and resuspended at 20×106 cells/mL. Cell suspensions are diluted with Matrigel to 2×106 cells/0.2 mL and delivered subcutaneously in the suprascapular region. Tumor growth is monitored to the volume of 100 mm3 when treatment begins (80 days). The observed rate of tumor take with LNCaP-AR-Lux cells is between 70% and 80%. Body weight and tumor volumes (width2×length/2) are measured two to three times per week with a digital caliper, and the average tumor volumes are determined. Test drugs are diluted in Tween 80:PEG 400, and stored at 4°C until administration by oral gavage. Each group of mice (n=7) is treated daily for 28 consecutive days with 1, 10, or 50 mg/kg Enzalutamide, vehicle control, or 50 mg/kg Bicalutamide. At the end of the treatment period or when tumor volume exceeded 1,000 mm3, animals are euthanized and blood and tissue samples are collected for analysis. Rats[4] Male SD rats (n=3) are administered Enzalutamide through the tail vein (intravenous) and by oral gavage at 1 mg/kg and are kept in metabolic cages after dosing. Urine and feces samples are collected over the following time intervals after dosing: 0-2, 2-4, 4-6, 6-10, 10-24, 24-48, and 48-72 h. The metabolic cages are rinsed with distilled water, and residues are added to the urine samples at 72 h. To extract the Enzalutamide present in the feces, samples are shaken vigorously for 12 h with 50 % methanol. |
| References |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| Density | 1.5±0.1 g/cm3 |
|---|---|
| Molecular Formula | C21H16F4N4O2S |
| Molecular Weight | 464.436 |
| Exact Mass | 464.093018 |
| PSA | 108.53000 |
| LogP | 2.13 |
| Index of Refraction | 1.630 |
| InChIKey | WXCXUHSOUPDCQV-UHFFFAOYSA-N |
| SMILES | CNC(=O)c1ccc(N2C(=S)N(c3ccc(C#N)c(C(F)(F)F)c3)C(=O)C2(C)C)cc1F |
This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Hazard Codes | Xi |
|---|---|
| HS Code | 2933990090 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
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~25%
Enzalutamide (M... CAS#:915087-33-1 |
| Literature: Regents of the University of California Patent: US2007/254933 A1, 2007 ; Location in patent: Page/Page column 7 ; |
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~79%
Enzalutamide (M... CAS#:915087-33-1 |
| Literature: MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott Patent: WO2011/106570 A1, 2011 ; Location in patent: Page/Page column 46 ; |
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~4%
Enzalutamide (M... CAS#:915087-33-1 |
| Literature: MEDIVATION PROSTATE THERAPEUTICS, INC.; JAIN, Rajendra, Parasmal; ANGELAUD, Remy; THOMPSON, Andrew; LAMBERSON, Carol; GREENFIELD, Scott Patent: WO2011/106570 A1, 2011 ; Location in patent: Page/Page column 48 ; |
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Enzalutamide (M... CAS#:915087-33-1 |
| Literature: WO2011/106570 A1, ; |
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Enzalutamide (M... CAS#:915087-33-1 |
| Literature: WO2011/106570 A1, ; |
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Enzalutamide (M... CAS#:915087-33-1 |
| Literature: WO2011/106570 A1, ; |
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Enzalutamide (M... CAS#:915087-33-1 |
| Literature: WO2011/106570 A1, ; |
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Enzalutamide (M... CAS#:915087-33-1 |
| Literature: WO2011/106570 A1, ; |
![4-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamide structure](https://image.chemsrc.com/caspic/085/915087-32-0.png)
![N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine methyl ester structure](https://image.chemsrc.com/caspic/377/1332524-01-2.png)
![4-[1-(4-cyano-3-trifluoromethyl-phenylcarbamoyl)-1-methyl-ethylamino]-2-fluoro-N- structure](https://image.chemsrc.com/caspic/470/1289942-55-7.png)
![N-[3-Fluoro-4-[(methylamino)carbonyl]phenyl]-2-methylalanine structure](https://image.chemsrc.com/caspic/215/1289942-66-0.png)
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 9 | |
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| DownStream 0 | |
This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.
| HS Code | 2933990090 |
|---|---|
| Summary | 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
This table contains target information, in‑vitro & in‑vivo assay data for this compound.
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| MDV3100 |
| MDV 3100 |
| Enzalutamide |
| 4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl]-2-fluoro-N-methylbenzamide |
| Enzalutamidum |
| 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-me |
| Xtandi |
| 4-{3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl}-2-fluoro-N-methylbenzamide |
| UNII-93T0T9GKNU |
| Enzalutamida |
| [14C]-Enzalutamide |
| MDV-3100 |
| 4-(3-(4-Cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide |
| N-methyl-4-[3-(4-cyano-3-trifluoromethylphenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]-2-fluorobenzamide |
| 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl]-2-fluoro-N-methylbenzamide |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: What is the SMILES notation of enzalutamide? |
| A: SMILES notation of enzalutamide is CNC(=O)c1ccc(N2C(=S)N(c3ccc(C#N)c(C(F)(F)F)c3)C(=O)C2(C)C)cc1F. |
| Q: What are the uses of enzalutamide? |
| A: Main uses of enzalutamide: Enzalutamide (MDV3100) is an androgen receptor (AR) antagonist with an IC50 of 36 nM in LNCaP prostate cells. |
| Q: What are the upstream materials of enzalutamide? |
| A: Related upstream materials(CAS) of enzalutamide: 915087-32-0;143782-23-4;1332524-01-2;463-71-8;112704-79-7;151982-51-3;749927-69-3;1289942-66-0;654-70-6. |
| Q: What is the InChIKey of enzalutamide? |
| A: InChIKey of enzalutamide is WXCXUHSOUPDCQV-UHFFFAOYSA-N. |
| Q: What is the LogP of enzalutamide? |
| A: LogP of enzalutamide is 2.13. |
| Q: What is the CAS number of enzalutamide? |
| A: CAS number of enzalutamide is 915087-33-1. |
| Q: What is the polar surface area (PSA) of enzalutamide? |
| A: Polar surface area (PSA) of enzalutamide is 108.53000. |
| Q: What is the molecular weight of enzalutamide? |
| A: Molecular weight of enzalutamide is 464.436. |
| Q: What is the molecular formula of enzalutamide? |
| A: Molecular formula of enzalutamide is C21H16F4N4O2S. |
| Q: What is the English name of enzalutamide? |
| A: The English name of enzalutamide is enzalutamide. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| Henan Tianfu Chemical Co., Ltd. |