Y0001448
Bicalutamide for system suitability
European Pharmacopoeia (EP) Reference Standard
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All Photos(1)
Synonym(s):
Bicalutamide (CDX), Casodex, Cosudex, N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
Empirical Formula (Hill Notation):
C18H14F4N2O4S
CAS Number:
Molecular Weight:
430.37
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24
Recommended Products
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.
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Pricing
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 1 - Carc. 2 - Repr. 1B
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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High SPDEF may identify patients who will have a prolonged response to androgen deprivation therapy.
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
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.
Manfred P Wirth et al.
Oncology, 65 Suppl 1, 1-4 (2003-09-02)
Adjuvant hormonal therapy has been demonstrated to be able to delay disease progression in nonmetastatic prostate cancer. To date, however, a favorable impact on survival has only been demonstrated in lymph-node-positive disease and in external-beam radiotherapy series with locally advanced
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
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
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