Enzalutamide (MDV3100)
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MedKoo CAT#: 201821

CAS#: 915087-33-1

Description: Enzalutamide, also known as MDV3100, is an orally bioavailable, organic, non-steroidal small molecule targeting the androgen receptor (AR) with potential antineoplastic activity. Through a mechanism that is reported to be different from other approved AR antagonists, selective androgen receptor modulator MDV3100 inhibits the activity of prostate cancer cell ARs, which may result in a reduction in prostate cancer cell proliferation and, correspondingly, a reduction in the serum prostate specific antigen (PSA) level. In August 2012, the United States (U.S.) Food and Drug Administration (FDA) approved enzalutamide for the treatment of castration-resistant prostate cancer.

Chemical Structure

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Enzalutamide (MDV3100)
CAS# 915087-33-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 201821
Name: Enzalutamide (MDV3100)
CAS#: 915087-33-1
Chemical Formula: C21H16F4N4O2S
Exact Mass: 464.09
Molecular Weight: 464.430
Elemental Analysis: C, 54.31; H, 3.47; F, 16.36; N, 12.06; O, 6.89; S, 6.90

Price and Availability

Size Price Availability Quantity
100mg USD 90 Ready to ship
500mg USD 250 Ready to ship
1g USD 425 Ready to ship
2g USD 700 Ready to ship
5g USD 1300 Ready to ship
10g USD 2050 Ready to ship
20g USD 2950 Ready to ship
50g USD 4950 Ready to ship
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Synonym: MDV3100; MDV 3100; MDV-3100; Enzalutamide brand name: Xtandi.

IUPAC/Chemical Name: 4-(3-(4-cyano-3-(trifluoromethyl)phenyl)-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl)-2-fluoro-N-methylbenzamide

InChi Key: WXCXUHSOUPDCQV-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-4-11(10-26)15(8-12)21(23,24)25)19(32)29(20)13-6-7-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)

SMILES Code: O=C(NC)C1=CC=C(N(C(N2C3=CC=C(C#N)C(C(F)(F)F)=C3)=S)C(C)(C)C2=O)C=C1F

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: MDV 3100 was found clinically active for metastatic castration-resistant prostate cancer patients in ongoing phase I and II trials. PSA level decreased more than 50 percent in 40/65 chemo-naive patients and 38/75 chemotherapy-treated patients. Recent long-term follow up data from these early clinical studies, announced in February 2011, were positive. Median time to radiographic progression was 56 weeks for chemo-naive patients and 25 weeks for the post-chemotherapy population.  Medivation is conducting an international phase III trial that began in September 2009 known as AFFIRM. The trial will determine the effectiveness of MDV3100 in patients who have previously failed chemotherapy treatment with docetaxel.  In November 2011, this trial was halted after an interim analysis revealed that patients given the drug lived for approximately 5 months longer than those taking placebo. Medivation is expected to file for FDA approval sometime in 2012.  There is another phase III trial, known as PREVAIL, that is investigating the effectiveness of MDV3100 with patients who have not yet received chemotherapy. As of October 2011, this trial is still open to accrual. In addition, a phase II trial began in March 2011 comparing MDV3100 with a commonly used anti-androgen, bicalutamide, in prostate cancer patients who have progressed while on LHRH analogue therapy (e,g., leuprorelin) or surgical castration. For detail see wikipedia.com.      

Biological target: AR antagonist with an IC50 of 36 nM in LNCaP prostate cells
In vitro activity: Myeloid cell function is influenced by their metabolic activity. To investigate whether AR blockade altered metabolism in myeloid cells, MDSCs were generated in vitro in the presence of enzalutamide and metabolic changes were assessed using Seahorse technology. Mitochondrial respiration parameters, such as basal respiration, ATP production from oxidative phosphorylation and maximal respiration, were downregulated in MDSCs treated with enzalutamide when compared to DMSO-treated MDSCs (Figures 4A andB). Enzalutamide treatment led to increased glycolytic rate and reduced glycolytic reserve in MDSCs when compared to DMSO-treated controls (Figures 4C andD). Graphing of ECAR vs. OCR showed increase in ECAR in MDSCs treated with enzalutamide (Figure 4E). WT BMDMs treated in vitro with enzalutamide or BMDMs generated from bone marrow of MARKO mice also exhibited decreased mitochondrial respiration and increased glycolysis (Figure 4F). The metabolic changes induced by enzalutamide were dependent on AR, as treatment of MARKO BMDMs with enzalutamide did not alter these metabolic changes (Figure 4F). In addition, in vitro treatment of tumor-associated CD11b+ cells from human prostate tumor xenografts models PC3M and PCaX led to a similar metabolic shift, indicating that tumor-associated myeloid cell metabolism was altered by AR inhibition (Figures 4G,H). Reference: Cancer Immunol Res. 2020 Sep; 8(9): 1215–1227. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7484281/
In vivo activity: Human bone tumor biopsy studies show that androgen production is present in bone tumors and activation of AR signaling contributes to bone tumor growth. To determine how ERG induced androgen synthesis contributes to bone tumor growth and whether ERG activity can be a predictor for anti-androgen therapy responsiveness, we utilized an intratibial bone tumor growth model with VCaP scr and ERG shRNA cells to address these questions. Tumor growth analysis of both cells lines show that VCaP ERG shRNA cells grow more slowly, requiring 4 weeks longer to reach similar growth sizes as assessed by luciferase imaging (Fig. 3a and d). When both tumors reach comparable size, the animals bearing bone tumors were randomized and treated with vehicle (Tween 80) or Enzalutamide by oral gavage. Tumor growth rate is slower in VCaP shERG tumors compared to scr shRNA tumors (Fig.3b and d). Enzalutamide treatment resulted in significant reduction in tumor burden in VCaP scr shRNA group compared to VCaP shERG group (Fig.3c and d). These data suggest that ERG signaling contributes to bone tumor growth and that AR targeting with enzalutamide significantly inhibits the bone tumor growth presumably through interfering with reduced ERG signaling. References: BMC Cancer. 2019; 19: 972. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6802314/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.0 107.66

Preparing Stock Solutions

The following data is based on the product molecular weight 464.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Consiglio CR, Udartseva O, Ramsey KD, Bush C, Gollnick SO. Enzalutamide, an Androgen Receptor Antagonist, Enhances Myeloid Cell-Mediated Immune Suppression and Tumor Progression. Cancer Immunol Res. 2020 Sep;8(9):1215-1227. doi: 10.1158/2326-6066.CIR-19-0371. Epub 2020 Jul 13. PMID: 32661092; PMCID: PMC7484281. 2. Semaan L, Mander N, Cher ML, Chinni SR. TMPRSS2-ERG fusions confer efficacy of enzalutamide in an in vivo bone tumor growth model. BMC Cancer. 2019 Oct 21;19(1):972. doi: 10.1186/s12885-019-6185-0. PMID: 31638934; PMCID: PMC6802314.
In vitro protocol: 1. Consiglio CR, Udartseva O, Ramsey KD, Bush C, Gollnick SO. Enzalutamide, an Androgen Receptor Antagonist, Enhances Myeloid Cell-Mediated Immune Suppression and Tumor Progression. Cancer Immunol Res. 2020 Sep;8(9):1215-1227. doi: 10.1158/2326-6066.CIR-19-0371. Epub 2020 Jul 13. PMID: 32661092; PMCID: PMC7484281.
In vivo protocol: 1. Semaan L, Mander N, Cher ML, Chinni SR. TMPRSS2-ERG fusions confer efficacy of enzalutamide in an in vivo bone tumor growth model. BMC Cancer. 2019 Oct 21;19(1):972. doi: 10.1186/s12885-019-6185-0. PMID: 31638934; PMCID: PMC6802314.

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