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90357-06-5 (Bicalutamide)

1

Identification

Bicalutamide Bicalutamide
Name Bicalutamide
Formula C18H14F4N2O4S
MW 430.37
CAS No. 90357-06-5
EINECS
Smiles FC1=CC=C(S(=O)(CC(O)(C(NC2=CC=C(C#N)C(C(F)(F)F)=C2)=O)C)=O)C=C1
Synonyms Cosudex;Casodex; N-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophenyl)sulfonyl)-2-hydroxy-2-methylpropanamide
InChI 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)
2

Introduction

Bicalutamide(Casodex) is an oral non-steroidal anti-androgen for prostate cancer; binds to the androgen receptor.

Background Information

Nonsteroidal antiandrogen, competitively binds to cytosolic androgen receptors and inhibiting the receptor binding of androgens ......by AOBIOUS INC
Bicalutamide (marketed as Casodex, Cosudex, Calutide, Kalumid) is a non-steriodal Androgen Receptor (AR) inhibitor. Bicalutamide (CDX) is inhibited by non-genomic, transcription-independent stimulation of PI3K/AKT phosphorylation by androgens. Bicalutamide displays peripheral selectivity and does not effect serum levels of LH and testosterone. Bicalutamide exhibits potent anticancer activity in vivo. Bicalutamide acts as a pure anti-androgen by binding to the androgen receptor (AR) and preventing the activation of the AR and subsequent upregulation of androgen responsive genes by androgenic hormones. In addition, bicalutamide accelerates the degradation of the androgen receptor. Bicalutamide is induces cell death by a pathway that is independent of changes in mitochondrial membrane potential and Bcl-2 action. Bicalutamide is currently tested for treatment of andogen receptor positive ER-/PR- metastatic breast cancer. ......by AbMole BioScience
Bicalutamide is an oral non-steroidal anti-androgen used in the treatment of prostate cancer and hirsutism. ......by AdooQ BioScience, LLC
Bicalutamide is a non-steroidal androgen receptor (AR) antagonist with IC50 of 0.16 μM. ......by BOC Sciences
R-Bicalutamide is a first-generation antiandrogen that inhibits androgen action by competitively binding to the androgen receptor (AR). With other anti-androgens, R-bicalutimide decreases levels of Bcl-2, Bcl-XL, caspase-3, and PARP, induces apoptosis, and inhibits cell growth of prostate cancer cells. In similar animal models, this compound decreases plasma PSA levels and suppresses tumor growth. Bicalutamide binds the androgen receptor in two sites, distorting coactivator binding and inhibiting transcription. ......by BioVision, Inc.,
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. ......by MedKoo Biosciences, Inc.
Bicalutamide is an androgen receptor (AR) antagonist with IC50 of 0.16 μM in LNCaP/AR(cs)cell line. ......by Selleck Chemicals LLC
Bicalutamide is an oral non-steroidal anti-androgen for prostate cancer. It binds to the androgen receptor. ......by Target Molecule Corp.
Orally active non-steroidal androgen receptor antagonist (IC50 = 190 nM). Displays peripheral selectivity and does not effect serum levels of LH and testosterone. Exhibits potent anticancer activity in vivo. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Cell lines C4-2 cell
Conditions 0-1 μM; 72 hours
Method Exponentially growing C4-2 cells are plated into two 96-well plates and incubated overnight at 37 ˚C. Twenty-four hours later one plate is aspirated and stored at -80 ˚C and the other treated with 10-fold serial concentrations of ridaforolimus (1000 nM to 0.0001 nM) or vehicle (ethanol). Following 72 hours culture at 37 ˚C, the plates are assessed simultaneously for cell growth using the Cy qUANT Cell Proliferation Assay kit. Bicalutamide and Ridaforolimus combination proliferation assays are performed similarly except cell growth is determined as the change in cell number between vehicle control and compound treated cells after 72 hours in culture.
Source Selleck Chemicals LLC

Animal Experiment

Animal Models Male nude mice bearing C4-2 cells
Dosage 10 mg/kg
Formulation 4% ethanol, 5% Tween 80, and 5% propylene glycol
Administration Administered via p.o.
Source Selleck Chemicals LLC
4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000023844

Storage condition

Storage condition:Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). Stock solution storage:0 - 4 C for short term (days to weeks), or -20 C for long term (months). 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. by MedKoo Biosciences, Inc.
Store at RT by Tocris Bioscience Inc.

Solubility

DMSO 86 mg/mL Water <1 mg/mL Ethanol 7mg/mL by MedChemexpress Co., Ltd.
Soluble in DMSO, not in water by MedKoo Biosciences, Inc.
(25°C) * In vitro DMSO 86 mg/mL (199.82 mM); Ethanol5 mg/mL (11.61 mM); Water<1 mg/mL (<1 mM) by Selleck Chemicals LLC
Soluble to 100 mM in DMSO and to 10 mM in ethanol by Tocris Bioscience Inc.
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Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Bicalutamide GlaxoSmithKline plc Hormone refractory prostate cancer 2007/5/31 2013/2/1 Phase 4 Clinical
Bicalutamide AstraZeneca plc Prostate tumor 2003/6/30 Phase 4 Clinical
Bicalutamide AstraZeneca plc Prostate tumor 2004/8/31 Phase 4 Clinical
Bicalutamide University of Tampere Prostate tumor 2004/10/31 2006/11/30 Phase 4 Clinical
Bicalutamide Ferring Pharmaceuticals Inc Metastatic prostate cancer 2009/4/30 2010/7/31 Phase 3 Clinical
Bicalutamide - Launched
7

Safety Data of Bicalutamide

Hazard Symbols : Xi
Risk Statements : 36/37/38
Safety Statements : 26-36
HS Code : 29242995
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Spectral Information

9

Suppliers List

10

Related Products

Other Forms of 90357-06-5

Name CAS No Formula MW

Recommended Compounds in Androgen Receptor Autophagy

Name CAS No Formula MW
Lupeol 545-47-1 C30H50O 426.72
Oxandrolone 53-39-4 C19H30O3 306.44
Testosterone (undecanoate) 5949-44-0 C30H48O3 456.7003
Spironolactone 52-01-7 C24H32O4S 416.57
LGD-4033 1165910-22-4 C14H12F6N2O 338.25
Adrenosterone 382-45-6 C19H24O3 300.39
Triptophenolide 74285-86-2 C20H24O3 312.4
Epiandrosterone 481-29-8 C19H30O2 290.44
3,3'-Diindolylmethane 1968-05-4 C17H14N2 246.31
Boldenone Undecylenate 13103-34-9 C30H44O3 452.67
Testosterone 58-22-0 C19H28O2 288.42
Cyproterone (acetate) 427-51-0 0.0
GLPG0492 1215085-92-9 C19H14F3N3O3 389.328
N-desmethyl Enzalutamide 1242137-16-1 C20H14F4N4O2S 450.41
AZD3514 1240299-33-5 C25H32F3N7O2 519.56
ARN-509 956104-40-8 C21H15F4N5O2S 477.43
DHEA 53-43-0 C19H28O2 288.42
RAD140 1182367-47-0 C20H16ClN5O2 393.83
Cortexolone 17 alpha-propionate 19608-29-8 C24H34O5 402.5238
BMS-564929 627530-84-1 C14H12ClN3O3 305.72

Recommended Compounds in Same Indication

Name CAS No Formula MW
TAK-700 (R-form) 752243-39-3 C18H17N3O2 307.35
Olaparib 763113-22-0 C24H23FN4O3 434.46
KX2-391 897016-82-9 C26H29N3O3 431.53
AT-101 90141-22-3 C30H30O8 518.55
Enzalutamide 915087-33-1 C21H16F4N4O2S 464.44
Tivozanib 475108-18-0 C22H19ClN4O5 454.86
Orteronel 566939-85-3 C18H17N3O2 307.35
Linsitinib 867160-71-2 C26H23N5O 421.49
Fenretinide 65646-68-6 C26H33NO2 391.55
Leuprolide (Acetate) 74381-53-6 C61H88N16O14 1269.45
Retaspimycin 857402-23-4 C31H45N3O8 587.7
Retaspimycin (Hydrochloride) 857402-63-2 C31H46ClN3O8 624.17
Bafetinib 859212-16-1 C30H31F3N8O 576.6154
AT13387 912999-49-6 C24H31N3O3 409.52
Ganetespib 888216-25-9 C20H20N4O3 364.4
Tasquinimod 254964-60-8 C20H17F3N2O4 406.36
Orteronel (racemate) 426219-18-3 C18H17N3O2 307.3465
TAK-700 (salt) 426219-53-6 C28H28N4O7 532.54
TOK-001 851983-85-2 C26H32N2O 388.55
RO4929097 847925-91-1 C22H20F5N3O3 469.4
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Route of Synthesis

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References

[1]. Nicola J. Clegg,1 John Wongvipat,1,2 Jim Joseph, ARN-509: a novel anti-androgen for prostate cancer treatment. Cancer Res. 2012 March 15; 72(6): 1494-1503.

[2]. RACHEL M. SQUILLACE, DAVID MILLER, SCOTT D. WARDWELL, Synergistic activity of the mTOR inhibitor ridaforolimus and the antiandrogen bicalutamide in prostate cancer models. Int J Oncol. 2012 August; 41(2): 425-432.

[3]. Nakabayashi M, Werner L, Courtney KD, Phase II trial of RAD001 and bicalutamide for castration-resistant prostate cancer. BJU Int. 2012 Dec;110(11):1729-35.

Protocol Reference

Furr et al (1987) ICI 176,334: a novel non-steroidal, peripherally selective antiandrogen. J.Endocrinol. 113 R7. PMID: 3625091.

Tucker et al (1988) Nonsteroidal antiandrogens. Synthesis and structure-activity relationships of 3-substituted derivatives of 2-hydroxypropionanilides. J.Med.Chem. 31 954. PMID: 3361581.

Furr and Tucker (1996) The preclinical development of bicalutamide: pharmacodynamics and mechanism of action. Urology 47 13. PMID: 8560673.

If you know of a relevant ......by Tocris Bioscience Inc.

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More Information

Bicalutamide

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