Enzalutamide, also known as MDV3100, CAS No. 915087-33-1, 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.

Product information

CAS Number: 915087-33-1

Molecular Weight: 464.44

Formula: C21H16F4N4O2S

Synonym:

MDV-3100

Xtandi

MDV 3100

MDV3100

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

Smiles: CC1(C)C(=O)N(C(=S)N1C1=CC(F)=C(C=C1)C(=O)NC)C1C=C(C(=CC=1)C#N)C(F)(F)F

InChiKey: WXCXUHSOUPDCQV-UHFFFAOYSA-N

InChi: 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)

Technical Data

Appearance: Solid Power

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

Solubility: Soluble in DMSO, not in water

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined.

HS Tariff Code: 382200

How to use

In Vitro:

MDV-3100 has greater affinity to AR than ICI 176334 does in a competition assay with 16β-[18F]fluoro-5α-DHT (18-FDHT) in castration-resistant LNCaP/AR cells (AR-overexpressing). While MDV-3100 shows no agonism in LNCaP/AR prostate cells. MDV-3100 antagonizes induction of prostate-specific antigen (PSA) and transmembrane serine protease 2 (TMPRSS2), combination with the synthetic androgen R1881 in parental LNCaP cells. MDV-3100 inhibits the transcriptional activity of a mutant AR protein (W741C, mutation of Trp741 to Cys). MDV-3100 also prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex.

In Vivo:

MDV-3100 induces great tumor regression in castrate male mice bearing LNCaP/AR xenografts at a dose of 10 mg/kg. MDV-3100 shows dose-independent pharmacokinetics at intravenous and oral doses of 0.5-5 mg/kg.

References:

1. El-Amm J, Patel N, Freeman A, Aragon-Ching JB. Metastatic Castration-Resistant Prostate Cancer: Critical Review of MDV-3100. Clin Med Insights Oncol. 2013 Aug 21;7:235-245. Review. PubMed PMID: 24179414; PubMed Central PMCID: PMC3813614.
2. Pal SK, Stein CA, Sartor O. MDV-3100for the treatment of prostate cancer. Expert Opin Pharmacother. 2013 Apr;14(5):679-85. doi: 10.1517/14656566.2013.775251. Epub 2013 Feb 27. Review. PubMed PMID: 23441761.
3. Ha YS, Goodin S, DiPaola RS, Kim IY. MDV-3100for the treatment of castration-resistant prostate cancer. Drugs Today (Barc). 2013 Jan;49(1):7-13. doi: 10.1358/dot.2013.49.1.1910724. Review. PubMed PMID: 23362491.
4. Rawlinson A, Mohammed A, Miller M, Kunkler R. The role of MDV-3100in the treatment of castration-resistant prostate cancer. Future Oncol. 2012 Sep;8(9):1073-81. doi: 10.2217/fon.12.99. Review. PubMed PMID: 23030482.

Products are for research use only. Not for human use.