Bicalutamide
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MedKoo CAT#: 100084

CAS#: 90357-06-5

Description: Bicalutamide is a synthetic, nonsteroidal antiandrogen. Bicalutamide competitively binds to cytosolic androgen receptors in target tissues, thereby inhibiting the receptor binding of androgens. This agent does not bind to most mutated forms of androgen receptors.

Chemical Structure

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Bicalutamide
CAS# 90357-06-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100084
Name: Bicalutamide
CAS#: 90357-06-5
Chemical Formula: C18H14F4N2O4S
Exact Mass: 430.06
Molecular Weight: 430.370
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 Quantity
100mg USD 150 Ready to ship
200mg USD 225 Ready to ship
500mg USD 450 Ready to ship
1g USD 650 Ready to ship
2g USD 1050 Ready to ship
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Synonym: ICI 176334; ICI-176334; ICI176334; Abbreviation: CDX. US brand name: Casodex. Foreign brand name: Cosudex.

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: According to http://en.wikipedia.org/wiki/Bicalutamide, Bicalutamide (marketed as Casodex, Cosudex, Calutide, Kalumid) is an oral non-steroidal anti-androgen used in the treatment of prostate cancer and hirsutism. It was first launched in 1995 as a combination treatment (with surgical or medical castration) for advanced prostate cancer and subsequently launched as monotherapy for the treatment of earlier stages of the disease. Bicalutamide is marketed by AstraZeneca with the brand names Casodex and Cosudex. It is recommended 50 mg once daily in combination with a luteinizing hormone-releasing hormone analogue or surgical castration.   DRUG DESCRIPTION CASODEX® (bicalutamide) Tablets contain 50 mg of bicalutamide, a non-steroidal androgen receptor inhibitor with no other known endocrine activity. Bicalutamide has a molecular weight of 430.37. The pKa' is approximately 12. Bicalutamide is a fine white to off white powder which is practically insoluble in water at 37°C (5 mg per 1000 mL), slightly soluble in chloroform and absolute ethanol, sparingly soluble in methanol, and soluble in acetone and tetrahydrofuran. CASODEX is a racemate with its antiandrogenic activity being almost exclusively exhibited by the R-enantiomer of bicalutamide; the S-enantiomer is essentially inactive. The inactive ingredients of CASODEX Tablets are lactose, magnesium stearate, hypromellose, polyethylene glycol, polyvidone, sodium starch glycollate, and titanium dioxide.    Mechanism of Action  Mechanism of Action CASODEX is a non-steroidal androgen receptor inhibitor. It competitively inhibits the action of androgens by binding to cytosol androgen receptors in the target tissue. Prostatic carcinoma is known to be androgen sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen. When CASODEX is combined with luteinizing hormone releasing hormone (LHRH) analog therapy, the suppression of serum testosterone induced by the LHRH analog is not affected. However, in clinical trials with CASODEX as a single agent for prostate cancer, rises in serum testosterone and estradiol have been noted. In a subset of patients who have been treated with CASODEX and an LHRH agonist, and who discontinue CASODEX therapy due to progressive advanced prostate cancer, a reduction in Prostate Specific Antigen (PSA) and/or clinical improvement (antiandrogen withdrawal phenomenon) may be observed. CASODEX is a non-steroidal androgen receptor inhibitor. It competitively inhibits the action of androgens by binding to cytosol androgen receptors in the target tissue. Prostatic carcinoma is known to be androgen sensitive and responds to treatment that counteracts the effect of androgen and/or removes the source of androgen. When CASODEX is combined with luteinizing hormone releasing hormone (LHRH) analog therapy, the suppression of serum testosterone induced by the LHRH analog is not affected. However, in clinical trials with CASODEX as a single agent for prostate cancer, rises in serum testosterone and estradiol have been noted. In a subset of patients who have been treated with CASODEX and an LHRH agonist, and who discontinue CASODEX therapy due to progressive advanced prostate cancer, a reduction in Prostate Specific Antigen (PSA) and/or clinical improvement (antiandrogen withdrawal phenomenon) may be observed.

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.0 100.00

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.

Recalculate based on batch purity %
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: 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.
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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