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B9061

Sigma-Aldrich

Bicalutamide (CDX)

≥98% (HPLC), powder

Synonym(s):

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:
12352200
PubChem Substance ID:
329773312
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated
protect from light

solubility

DMSO: >5 mg/mL
H2O: insoluble

originator

AstraZeneca

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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Application

Bicalutamide (CDX) has been used as an androgen receptor (AR) antagonist in prostate, bladder cancer cell lines and human fetal skeletal muscle cells. It has also been used as a supplement in RPMI 1640 for culturing androgen-independent LNCaP (LNCaP-AI) cell line.

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.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Nuclear Receptors (Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by AstraZeneca. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Benoît Boutin et al.
The Prostate, 73(10), 1090-1102 (2013-03-28)
Treatment of advanced prostate cancer (PCa) relies on pharmacological or surgical androgen deprivation. However, it is only temporarily efficient. After a few months or years, the tumor relapses despite the absence of androgenic stimulation: a state referred to as hormone-refractory
Päivi Östling et al.
Cancer research, 71(5), 1956-1967 (2011-02-24)
Androgen receptor (AR) is expressed in all stages of prostate cancer progression, including in castration-resistant tumors. Eliminating AR function continues to represent a focus of therapeutic investigation, but AR regulatory mechanisms remain poorly understood. To systematically characterize mechanisms involving microRNAs
Reactive stroma component COL6A1 is upregulated in castration-resistant prostate cancer and promotes tumor growth
Zhu YP, et al.
Testing, 6(16), 14488-14488 (2015)
Paucity of PD-L1 expression in prostate cancer: innate and adaptive immune resistance
Martin AM, et al.
Prostate Cancer and Prostatic Diseases, 18(4), 325-325 (2015)
Androgen receptor antagonist bicalutamide induces autophagy and apoptosis via ULK2 upregulation in human bladder cancer cells
Hao K, et al.
International Journal of Clinical and Experimental Pathology, 10(7), 7603-7615 (2017)
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