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Y0001448

Bicalutamide for system suitability

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:
Molecular Weight:
430.37
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
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 for system suitability 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

Signal Word

Danger

Hazard Statements

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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Paul R Sieber
Expert review of anticancer therapy, 7(12), 1773-1779 (2007-12-08)
Bicalutamide is a competitive nonsteroidal androgen receptor antagonist. In the European Union and a number of other countries, bicalutamide 150 mg per day is approved as an adjuvant to primary treatments (radical prostatectomy or radiotherapy) or as monotherapy as an
Andrew C Haller et al.
The Prostate, 74(5), 509-519 (2014-01-01)
Due to the indolent nature of prostate cancer, new prognostic measures are needed to identify patients with life threatening disease. SAM pointed domain-containing Ets transcription factor (SPDEF) has been associated with good prognosis and demonstrates an intimate relationship with the
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.
P W Wong et al.
Chest, 113(2), 548-550 (1998-03-14)
A 69-year-old man with advanced prostate cancer was receiving antiandrogen therapy (bicalutamide [Casodex]). He developed dyspnea, peripheral eosinophilia and bilateral pulmonary interstitial infiltrates. Transbronchial biopsy confirmed pulmonary eosinophilia. Withdrawal of bicalutamide and initiation of steroid therapy resulted in clinical improvement.

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