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

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.


Price and Availability

Size
Price

1g
USD 90
10g
USD 350
100g
USD 950
1kg
USD 3450
Size
Price

2g
USD 150
20g
USD 550
250g
USD 1450
2kg
USD 4950
Size
Price

5g
USD 250
50g
USD 750
500g
USD 2450
5kg
Ask price

Bicalutamide, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 100084
Name: Bicalutamide
CAS#: 90357-06-5
Chemical Formula: C18H14F4N2O4S
Exact Mass: 430.06104
Molecular Weight: 430.37
Elemental Analysis: C, 50.23; H, 3.28; F, 17.66; N, 6.51; O, 14.87; S, 7.45


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


Technical Data

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).

Harmonized System Code:
293490


Additional Information

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.


References

1: Gucalp A, Tolaney S, Isakoff SJ, Ingle JN, Liu MC, Carey LA, Blackwell KL, Rugo H, Nabell L, Forero-Torres A, Stearns V, Doane AS, Danso M, Moynahan ME, Momen LF, Gonzalez JM, Akhtar A, Giri D, Patil S, Feigin KN, Hudis CA, Traina TA. Phase II Trial of Bicalutamide in Patients with Androgen Receptor Positive, Hormone Receptor Negative Metastatic Breast Cancer. Clin Cancer Res. 2013 Aug 21. [Epub ahead of print] PubMed PMID: 23965901.

2: Li YF, Zhang SF, Zhang TT, Li L, Gan W, Jia HT, Xie S, Ji HH, He DL. Intermittent tri-weekly docetaxel plus bicalutamide in patients with castration-resistant prostate cancer: a single-arm prospective study using a historical control for comparison. Asian J Androl. 2013 Aug 19. doi: 10.1038/aja.2013.89. [Epub ahead of print] PubMed PMID: 23955552.

3: Lin TH, Izumi K, Lee SO, Lin WJ, Yeh S, Chang C. Anti-androgen receptor ASC-J9 versus anti-androgens MDV3100 (Enzalutamide) or Casodex (Bicalutamide) leads to opposite effects on prostate cancer metastasis via differential modulation of macrophage infiltration and STAT3-CCL2 signaling. Cell Death Dis. 2013 Aug 8;4:e764. doi: 10.1038/cddis.2013.270. PubMed PMID: 23928703.

4: Meulenbeld HJ, de Bono JS, Tagawa ST, Whang YE, Li X, Heath KH, Zandvliet AS, Ebbinghaus SW, Hudes GR, de Wit R. Tolerability, safety and pharmacokinetics of ridaforolimus in combination with bicalutamide in patients with asymptomatic, metastatic castration-resistant prostate cancer (CRPC). Cancer Chemother Pharmacol. 2013 Aug 7. [Epub ahead of print] PubMed PMID: 23921574.

5: Johnson TJ, Höti N, Liu C, Chowdhury WH, Li Y, Zhang Y, Lupold SE, Deweese T, Rodriguez R. Bicalutamide-activated oncolytic adenovirus for the adjuvant therapy of high-risk prostate cancer. Cancer Gene Ther. 2013 Jul;20(7):394-402. doi: 10.1038/cgt.2013.34. Epub 2013 Jun 14. PubMed PMID: 23764901; PubMed Central PMCID: PMC3732197.

6: Lin TH, Lee SO, Niu Y, Xu D, Liang L, Li L, Yeh SD, Fujimoto N, Yeh S, Chang C. Differential androgen deprivation therapies with anti-androgens casodex/bicalutamide or MDV3100/Enzalutamide versus anti-androgen receptor ASC-J9(R) Lead to promotion versus suppression of prostate cancer metastasis. J Biol Chem. 2013 Jul 5;288(27):19359-69. doi: 10.1074/jbc.M113.477216. Epub 2013 May 16. PubMed PMID: 23687298; PubMed Central PMCID: PMC3707641.

7: Li C, Wang JX, Le Y, Chen JF. Studies of bicalutamide-excipients interaction by combination of molecular docking and molecular dynamics simulation. Mol Pharm. 2013 Jun 3;10(6):2362-9. doi: 10.1021/mp300727d. Epub 2013 May 6. PubMed PMID: 23646858.

8: Boutin B, Tajeddine N, Vandersmissen P, Zanou N, Van Schoor M, Mondin L, Courtoy PJ, Tombal B, Gailly P. Androgen deprivation and androgen receptor competition by bicalutamide induce autophagy of hormone-resistant prostate cancer cells and confer resistance to apoptosis. Prostate. 2013 Jul;73(10):1090-102. doi: 10.1002/pros.22658. Epub 2013 Mar 26. PubMed PMID: 23532738.

9: Grosse L, Campeau AS, Caron S, Morin FA, Meunier K, Trottier J, Caron P, Verreault M, Barbier O. Enantiomer Selective Glucuronidation of the Non-Steroidal Pure Anti-Androgen Bicalutamide by Human Liver and Kidney: Role of the Human UDP-Glucuronosyltransferase (UGT)1A9 Enzyme. Basic Clin Pharmacol Toxicol. 2013 Aug;113(2):92-102. doi: 10.1111/bcpt.12071. Epub 2013 May 20. PubMed PMID: 23527766.

10: Argellati F, Nuzzo PV, Ricci F, Mangerini R, Rubagotti A, Boccardo F. Dihydrotestosterone and bicalutamide do not affect periostin expression in androgen-dependent LNCaP prostate cancer cell lines. Anticancer Res. 2013 Mar;33(3):815-20. PubMed PMID: 23482749.