Bicalutamide

Names

[ Name ]:
Bicalutamide

[Synonym ]:
(2R)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
Propanamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (2R)-
Bicaiutamide
(1E,2R)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanimidic acid
Propanimidic acid, N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-, (1E,2R)-
25mg
ODEX
BicalutaMide API
MFCD00869971
R-bicalutamide
Bicalutamide
R-Bicalutimide
Cosudex

Biological Activity

[Description]:

Bicalutamide is a non-steroidal androgen receptor inhibitor.

[Related Catalog]:

Signaling Pathways >> Others >> Androgen Receptor

Signaling Pathways >> Autophagy >> Autophagy

Research Areas >> Cancer

[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.

[Related Small Molecules]

ARN-509 | Dehydroepiandrosterone | Flutamide | ODM-201 | Danazol | 3,3'-Diindolylmethane | AZD3514 | RAD140 | BMS-564929 | GLPG0492 | Cyproterone acetate | LGD-4033 | Lupeol | Andarine | MK-0773

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
650.3±55.0 °C at 760 mmHg

[ Melting Point ]:
191-193°C

[ Molecular Formula ]:
C₁₈H₁₄F₄N₂O₄S

[ Molecular Weight ]:
430.373

[ Flash Point ]:
347.1±31.5 °C

[ Exact Mass ]:
430.061035

[ PSA ]:
115.64000

[ LogP ]:
4.94

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.578

[ Storage condition ]:
Store at RT

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TX1413500

CHEMICAL NAME :: Propanamide, N-(4-cyano-3-(trifluoromethyl)phenyl)-3-((4-fluorophe nyl)sulfonyl)-2-hydro xy-2- methyl-, (+-)-

CAS REGISTRY NUMBER :: 90357-06-5

LAST UPDATED :: 199712

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C18-H14-F4-N2-O4-S

MOLECULAR WEIGHT :: 430.40

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 22,75,1997

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 22,75,1997

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JTSCDR Journal of Toxicological Sciences. (Japanese Soc. of Toxicological Sciences, 4th Floor, Gakkai Center Bldg., 4-16, Yayoi 2-chome, Bunkyo-ku, Tokyo 113, Japan) V.1- 1976- Volume(issue)/page/year: 22,75,1997 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 420 mg/kg

SEX/DURATION :: female 21 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male Endocrine - changes in luteinizing hormone

REFERENCE :: ACENA7 Acta Endocrinologica (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) V.1- 1948- Volume(issue)/page/year: 125,547,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 420 mg/kg

SEX/DURATION :: female 21 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: ACENA7 Acta Endocrinologica (Copenhagen). (Periodica, Skolegade 12 E, DK-2500 Valby, Denmark) V.1- 1948- Volume(issue)/page/year: 125,547,1991

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36

[ RIDADR ]:
3077

[ RTECS ]:
TX1413500

[ Packaging Group ]:
III

[ Hazard Class ]:
9

[ HS Code ]:
2929909090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2929909090

[ Summary ]:
2929909090 other compounds with other nitrogen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

CYP3A5 regulates prostate cancer cell growth by facilitating nuclear translocation of AR.

Prostate 75(5) , 527-38, (2015)

The central role of androgen receptor (AR) signaling is established in prostate cancer growth and progression. We propose CYP3A5 is part of a feedback loop that modulates the sensitivity of AR to andr...

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. 288(27) , 19359-69, (2013)

Despite the fact that androgen deprivation therapy (ADT) can effectively reduce prostate cancer (PCa) size, its effect on PCa metastasis remains unclear. We examined the existing data on PCa patients ...

TLR3 engagement induces IRF-3-dependent apoptosis in androgen-sensitive prostate cancer cells and inhibits tumour growth in vivo.

J. Cell. Mol. Med. 19(2) , 327-39, (2015)

Toll-like receptors (TLRs) are a family of highly conserved transmembrane proteins expressed in epithelial and immune cells that recognize pathogen associated molecular patterns. Besides their role in...