Bicalutamide | CAS#90357-06-5 | Androgen receptor inhibitor

MedKoo Cat#: 100084 | Name: Bicalutamide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Bicalutamide is a first-generation nonsteroidal antiandrogen (NSAA) widely used for the treatment of prostate cancer. It binds competitively to androgen receptors (AR) and inhibits androgen-stimulated proliferation of prostate cancer cells. Bicalutamide has an IC₅₀ of ~160 nM for AR binding in vitro and shows potent AR antagonism in LNCaP cells with an IC₅₀ of around 100–200 nM. Clinically, it is typically administered at doses of 50 mg daily (monotherapy or combined with LHRH agonists) and achieves plasma concentrations of 8–12 µg/mL (about 20–30 µM), which is well above its effective in vitro levels. Bicalutamide’s efficacy has been demonstrated to reduce PSA levels and delay disease progression in hormone-sensitive prostate cancer, although resistance often develops due to AR mutations or overexpression.

Chemical Structure

Bicalutamide

CAS#90357-06-5

Theoretical Analysis

MedKoo Cat#: 100084

Name: Bicalutamide

CAS#: 90357-06-5

Chemical Formula: C18H14F4N2O4S

Exact Mass: 430.0610

Molecular Weight: 430.37

Elemental Analysis: C, 50.23; H, 3.28; F, 17.66; N, 6.51; O, 14.87; S, 7.45

Price and Availability

Size	Price	Availability
10mg	USD 65.00	Ready to Ship
50mg	USD 90.00	Ready to Ship
100mg	USD 150.00	Ready to ship
200mg	USD 250.00	Ready to ship
500mg	USD 450.00	Ready to ship
1g	USD 750.00	Ready to ship
2g	USD 1,250.00	Ready to ship

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Related CAS #

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Synonym

ICI 176334; ICI-176334; ICI176334; Abbreviation: CDX; Bicalutamide;

IUPAC/Chemical Name

N-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-methylpropanamide

InChi Key

LKJPYSCBVHEWIU-UHFFFAOYSA-N

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)

SMILES Code

O=C(NC1=CC=C(C#N)C(C(F)(F)F)=C1)C(C)(O)CS(=O)(C2=CC=C(F)C=C2)=O

Appearance

white solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#YYP30918

QC Data

View QC data: current batch, Lot#YYP30918

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Bicalutamide is an orally active non-steroidal androgen receptor (AR) antagonist.

In vitro activity:

Maximal decrease of telomerase activity was observed after 3 days of treatment by bicalutamide in LNCaPcells. Telomerase was not inhibited in LNCaP cells after 1 day of treatment and in DU145 cells after 1 or 3 days of treatment (Figure 3). The list of telomerase-related gene responses after bicalutamide treatment is presented in Table 2 (see Materials and Methods for design of microarray experiments). Moreover, in LNCaP cells this study found a decrease of TERT after both 1 day (8.5 and 5.6 fold) and 3 days (29.4 fold) of bicalutamide treatment. The expression of TERT was not changed in DU145 cells. The decrease of telomerase activity in LNCaP cells was also accompanied by a decrease in the mRNA level of MYC, androgen receptor, dyskerin and chaperone proteins HSP90, p23 and Hsp70Hsp90-organizing protein (Table 2). Reference: J Pharm Pharmacol. 2005 Jan;57(1):83-92. https://pubmed.ncbi.nlm.nih.gov/15638997/

In vivo activity:

Administration of bicalutamide or vehicle to mice bearing KUCaP was started 1 week before the castration and continued for 3 more weeks until the sacrifice. Although KUCaP treated with vehicle regressed after castration, KUCaP treated with bicalutamide continued to grow even after castration ( Fig. 4B). In castrated mice treated with vehicle, PSA level was <0.2 ng/mL in all animals. However, serum PSA level in castrated mice treated with bicalutamide did not decrease—93.5 ± 30.7 ng/mL (mean ± SD)—but is even higher than PSA levels in mice without hormonal manipulation ( Fig. 4C). These results suggested that antiandrogen bicalutamide had an agonistic activity to W741C mutant AR in vivo. Bicalutamide-treated KUCaP in castrated mice had very similar histology to KUCaP in male mice without hormonal manipulation, suggesting that bicalutamide functioned as a substitution of testicular androgen even after castration in KUCaP ( Fig. 4D-F). Reference: Cancer Res. 2005 Nov 1;65(21):9611-6. https://cancerres.aacrjournals.org/content/65/21/9611.long

	Solvent	mg/mL	mM
Solubility
	DMSO	43.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 430.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Chen KC, Chen CR, Chen CY, Tzou KY, Peng CC, Peng RY. Bicalutamide Elicits Renal Damage by Causing Mitochondrial Dysfunction via ROS Damage and Upregulation of HIF-1. Int J Mol Sci. 2020 May 11;21(9):3400. doi: 10.3390/ijms21093400. PMID: 32403414; PMCID: PMC7247665. 2. Bouchal J, Baumforth KR, Sváchová M, Murray PG, von Angerer E, Kolár Z. Microarray analysis of bicalutamide action on telomerase activity, p53 pathway and viability of prostate carcinoma cell lines. J Pharm Pharmacol. 2005 Jan;57(1):83-92. doi: 10.1211/0022357055164. PMID: 15638997. 3. Browne G, Nesbitt H, Ming L, Stein GS, Lian JB, McKeown SR, Worthington J. Bicalutamide-induced hypoxia potentiates RUNX2-mediated Bcl-2 expression resulting in apoptosis resistance. Br J Cancer. 2012 Nov 6;107(10):1714-21. doi: 10.1038/bjc.2012.455. Epub 2012 Oct 16. PMID: 23073173; PMCID: PMC3493869. 4. Yoshida T, Kinoshita H, Segawa T, Nakamura E, Inoue T, Shimizu Y, Kamoto T, Ogawa O. Antiandrogen bicalutamide promotes tumor growth in a novel androgen-dependent prostate cancer xenograft model derived from a bicalutamide-treated patient. Cancer Res. 2005 Nov 1;65(21):9611-6. doi: 10.1158/0008-5472.CAN-05-0817. PMID: 16266977.

In vitro protocol:

In vivo protocol:

1. Browne G, Nesbitt H, Ming L, Stein GS, Lian JB, McKeown SR, Worthington J. Bicalutamide-induced hypoxia potentiates RUNX2-mediated Bcl-2 expression resulting in apoptosis resistance. Br J Cancer. 2012 Nov 6;107(10):1714-21. doi: 10.1038/bjc.2012.455. Epub 2012 Oct 16. PMID: 23073173; PMCID: PMC3493869. 2. Yoshida T, Kinoshita H, Segawa T, Nakamura E, Inoue T, Shimizu Y, Kamoto T, Ogawa O. Antiandrogen bicalutamide promotes tumor growth in a novel androgen-dependent prostate cancer xenograft model derived from a bicalutamide-treated patient. Cancer Res. 2005 Nov 1;65(21):9611-6. doi: 10.1158/0008-5472.CAN-05-0817. PMID: 16266977.

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