BicalutamideAn androgen receptor inhibitor useful in prostate cancer research

Bicalutamide (CAS 90357-06-5)

Bicalutamide | CAS 90357-06-5 is rated 5.0 out of 5 by 1.
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Synonym: Casodex; N-(4-Cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-methylpropanamide
Application: An androgen receptor inhibitor useful in prostate cancer research
CAS Number: 90357-06-5
Purity: ≥98%
Molecular Weight: 430.37
Molecular Formula: C18H14F4N2O4S
* Refer to Certificate of Analysis for lot specific data (including water content).
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Bicalutamide is a nonsteroidal androgen receptor inhibitor useful in prostate cancer research. Bicalutamide induces cell death by a pathway that is independent of changes in mitochondrial membrane potential and Bcl-2 action.


References

Antiproliferative activity of casodex (ICI 176.334) in hormone-dependent tumours: A. Maucher & E. von Angerer; J. Cancer Res. Clin. Oncol. 119, 669 (1993) Antiandrogen-induced cell death in LNCaP human prostate cancer cells: E.C. Lee, et al.; Cell Death Differ. 10, 761 (2003) Proanthocyanidins from grape seeds inhibit expression of matrix metalloproteinases in human prostate carcinoma cells, which is associated with the inhibition of activation of MAPK and NF kappa B: P.K. Vayalil, et al.; Carcinogenesis 25, 987 (2004) Wnt3a growth factor induces androgen receptor-mediated transcription and enhances cell growth in human prostate cancer cells: M. Verras, et al.; Cancer Res. 64, 8860 (2004) Glycogen synthase kinase-3beta activity is required for androgen-stimulated gene expression in prostate cancer: X. Liao, et al.; Endocrinology 145, 2941 (2004) A phase I pharmacokinetic and pharmacodynamic study of OGX-011, a 2'-methoxyethyl antisense oligonucleotide to clusterin, in patients with localized prostate cancer: K.N. Chi, et al.; J. Natl. Cancer Inst. 97, 1287 (2005) The mechanisms and managements of hormone-therapy resistance in breast and prostate cancers: K.M. Rau, et al.; Endocr. Relat. Cancer 12, 511 (2005), Signal transduction pathways in androgen-dependent and -independent prostate cancer cell proliferation: P.M. Ghosh, et al.; Endocr. Relat. Cancer 12, 119 (2005) Recent advances on multiple tumorigenic cascades involved in prostatic cancer progression and targeting therapies: M. Mimeault & S.K. Batra; Carcinogenesis 27, 1 (2006), Bcl-xL is overexpressed in hormone-resistant prostate cancer and promotes survival of LNCaP cells via interaction with proapoptotic Bak: C. Castilla, et al.; Endocrinology 147, 4960 (2006) Androgen receptor corepressors and prostate cancer: C.J. Burd, et al.; Endocr. Relat. Cancer 13, 979 (2006), Par-4-dependent apoptosis by the dietary compound withaferin A in prostate cancer cells: S. Srinivasan, et al.; Cancer Res. 67, 246 (2006) Androgen receptor structural and functional elements: role and regulation in prostate cancer: S.M. Dehm & D.J. Tindall; Mol. Endocrinol. 21, 2855 (2007)Phosphoinositide 3-kinase-independent non-genomic signals transit from the androgen receptor to Akt1 in membrane raft microdomains: B. Cinar, et al.; JBC 282, 29584 (2007) A novel class of pyranocoumarin anti-androgen receptor signaling compounds: J. Guo, et al.; Mol. Cancer Ther. 6, 907 (2007) Increased resistance to trail-induced apoptosis in prostate cancer cells selected in the presence of bicalutamide: M. Mitterberger, et al.; Prostate 67, 1194 (2007) Interplay of nuclear factor-kappaB and B-myb in the negative regulation of androgen receptor expression by tumor necrosis factor alpha: S. Ko, et al.; Mol. Endocrinol. 22, 273 (2008)

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in DMSO (86 mg/ml at 25° C), DMF (~20 mg/ml), ethanol (7 mg/ml at 25° C), and methanol (slightly). Insoluble in water.
Storage :
Store at -20° C
Melting Point :
191-193° C
Boiling Point :
650.31° C at 760 mmHg (Predicted)
Density :
1.52 g/cm3 (Predicted)
Refractive Index :
n20D 1.58 (Predicted)
IC50 :
Androgen Receptor: IC50 = 25 nM (rat); Displacement of [17-α-methyl-3H]mibolerone: IC50 = 120 nM; Androgen Receptor: IC50 = 0.16 µM; VP16-AR–mediated transcription: IC50 = 0.35 µM
Ki Data :
Androgen Receptor: Ki= 14 nM (rat); Progesterone receptor: Ki= 7.2 µM (rat); GR: Ki= >100 µM (human); ERα: Ki= >100 µM (human)
pK Values :
pKa: 11.49 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
TX1413500
PubChem CID :
2375
Merck Index :
14: 1200
MDL Number :
MFCD00869971
SMILES :
CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O

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Bicalutamide  Product Citations

See how others have used Bicalutamide. Click on the entry to view the PubMed entry .

Citations 1 to 6 of 6 total

PMID: # 26954717  Byrne, NM. et al. 2016. British journal of cancer. 114: 659-68.

PMID: # 26189652  Nesbitt, H. et al. 2016. J. Cell. Physiol. 231: 473-82.

PMID: # 26385866  Warkus, EL. et al. 2016. Toxicol. Sci. 149: 15-30.

PMID: # 24648996  Otsuka, T. et al. 2013. Biomedical reports. 1: 614-618.

PMID: # 23603339  Belic, A. et al. 2013. Chemico-biological interactions. 203: 597-603.

PMID: # 22614062  Colquhoun, AJ. et al. 2012. Prostate cancer and prostatic diseases. 15: 346-52.

Citations 1 to 6 of 6 total

What is the shelf life of the compound when dissolved in DMSO?  How should this be stored when dissolved in DMSO?

Asked by: two2igm05
Thank you for your question. We suggest to store this product in it's original form in the original vial as much as possible. Ideally, the DMSO solution would be made and used the same day. If necessary, aliquot out the DMSO solution and store at -20ºC. Please avoid repeated freeze-thaw cycles. Please contact Technical Service if you have further questions concerning this product.
Answered by: Tech Service 9
Date published: 2017-01-16
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Rated 5 out of 5 by from Zhu Zhu, Y. et al. (PubMed 25995342) found that Bicalutamide (Casodex) and enzalutamide, androgen receptor (AR) inhibitors, desensitize docetaxel-resistant prostate cancer cells to docetaxel treatment independent of AR status. -SCBT Publication Review
Date published: 2015-01-13
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