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Y0001444

Bicalutamide

European Pharmacopoeia (EP) Reference Standard

Synonym(s):

Bicalutamide (CDX), Casodex, Cosudex, N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide

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About This Item

Empirical Formula (Hill Notation):
C18H14F4N2O4S
CAS Number:
90357-06-5
Molecular Weight:
430.37
MDL number:
MFCD00869971
UNSPSC Code:
41116107
PubChem Substance ID:
329831426
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

bicalutamide

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

CC(O)(CS(=O)(=O)c1ccc(F)cc1)C(=O)Nc2ccc(C#N)c(c2)C(F)(F)F

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

Gene Information

human ... AR(367)

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Bicalutamide EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.

Biochem/physiol Actions

Bicalutamide (CDX) is a non-steriodal Androgen Receptor (AR) antagonist and a pure antiandrogen. It acts via balancing histone acetylation/deacetylation and recruitment of coregulators. Bicalutamide (CDX) abolishes androgen-mediated expression. For example, MMP13 upregulation in prostate cancer, PLZF (promyelocytic leukemia zinc finger protein), and GADD45γ (growth arrest and DNA damage inducible, gamma). Bicalutamide (CDX) is inhibited by non-genomic, transcription-independent stimulation of PI3K/AKT phosphorylation by androgens.

Packaging

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Other Notes

Sales restrictions may apply.

Pictograms

Health hazardEnvironment
GHS08,GHS09

Signal Word

Danger

Hazard Statements

H351,H360FD,H410

Hazard Classifications

Aquatic Chronic 1 - Carc. 2 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Brian D Lehmann et al.
Breast cancer research : BCR, 16(4), 406-406 (2014-08-12)
Triple negative breast cancer (TNBC) is a heterogeneous collection of biologically diverse cancers, which contributes to variable clinical outcomes. Previously, we identified a TNBC subtype that has a luminal phenotype and expresses the androgen receptor (AR+). TNBC cells derived from
Wiebke Hessenkemper et al.
Molecular endocrinology (Baltimore, Md.), 28(11), 1831-1840 (2014-09-10)
We have previously identified a natural occurring, androgen receptor-specific antagonist. Atraric acid (AA) inhibits the transactivation of the androgen receptor (AR) and androgen-mediated growth of AR-expressing human prostate cancer (PCa) cell lines. Here we show that AA treatment of living
Manfred P Wirth et al.
Frontiers of radiation therapy and oncology, 41, 39-48 (2008-06-12)
Several randomized trials have demonstrated that adjuvant medical or surgical castration may improve overall survival in patients with locally advanced prostate cancer undergoing external beam radiotherapy. After radical prostatectomy, patients with positive lymph nodes seem to benefit from adjuvant hormonal
G J Kolvenbag et al.
The Prostate, 34(1), 61-72 (1998-01-15)
Bicalutamide (Casodex) is a new nonsteroidal antiandrogen developed for use in patients with prostate cancer. The efficacy and tolerability of bicalutamide as monotherapy and as combination therapy for patients with advanced prostate cancer have been evaluated in randomized clinical trials.
Min Shen et al.
Journal of cellular physiology, 229(6), 688-695 (2013-10-17)
AMP-activated protein kinase (AMPK) has recently emerged as a potential target for cancer therapy due to the observation that activation of AMPK inhibits tumor cell growth. It is well-known that androgen receptor (AR) signaling is a major driver for the
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