A non-steroidal antiandrogen
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Labeled Version(s)
22377Bicalutamide-d4
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Bicalutamide

Item No. 14250

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-propanamide
CAS Number
90357-06-5
Synonyms
  • ICI 176334
  • ZD 176334
Molecular Formula
C18H14F4N2O4S
Formula Weight
430.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:5): 0.16 mg/mlDMSO: 14 mg/mlEthanol: 1 mg/ml
λmax
215, 271 nm
SMILES
OC(CS(C1=CC=C(F)C=C1)(=O)=O)(C)C(NC2=CC(C(F)(F)F)=C(C#N)C=C2)=O
InChi Code
InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
InChi Key
LKJPYSCBVHEWIU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Bicalutamide is a non-steroidal androgen receptor antagonist that binds the androgen receptor (Ki = 12.5 μM; IC50 = 1.2 μM), preventing its activation and subsequent upregulation of androgen responsive genes by androgenic hormones.1,2 Bicalutamide is frequently used to examine the role of androgen receptor inactivation in the proliferation of prostate cancer cells and has served as a molecular template for the design and structural optimization of more selective androgen receptor modulators for androgen therapy.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Freeman, S.N., Mainwaring, W.I.P., and Furr, B.J.A. A possible explanation for the peripheral selectivity of a novel non-steroidal pure antiandrogen, Casodex (ICI 176,334). Br. J. Cancer 60(5), 664-668 (1989).

    2. Masiello, D., Cheng, S., Bubley, G.J., et al. Bicalutamide functions as an androgen receptor antagonist by assembly of a transcriptionally inactive receptor. The Journal of Biological Chemisty 277(29), 26321-26326 (2002).

    3. Gao, W., Kim, J., and Dalton, J.T. Pharmacokinetics and pharmacodynamics of nonsteroidal androgen receptor ligands. Pharmacol. Res. 23(8), 1641-1658 (2006).

    4. Yin, D., Perera, M.A., Dalton, J.T., et al. Key structural features of nonsteroidal ligands for binding and activation of the androgen receptor. Mol. Pharmacol. 63(1), 211-223 (2003).