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113299-40-4 molecular structure
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(2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide

ChemBase ID: 73102
Molecular Formular: C18H14F4N2O4S
Molecular Mass: 430.3733728
Monoisotopic Mass: 430.06104082
SMILES and InChIs

SMILES:
C(=O)([C@@](CS(=O)(=O)c1ccc(cc1)F)(C)O)Nc1cc(c(cc1)C#N)C(F)(F)F
Canonical SMILES:
N#Cc1ccc(cc1C(F)(F)F)NC(=O)[C@](CS(=O)(=O)c1ccc(cc1)F)(O)C
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)/t17-/m0/s1
InChIKey:
LKJPYSCBVHEWIU-KRWDZBQOSA-N

Cite this record

CBID:73102 http://www.chembase.cn/molecule-73102.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
IUPAC Traditional name
bicalutamide
(2R)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
Synonyms
N-[4-Cyano-3-trifluoromethyl)phenyl]- 3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide-d4
ICI-176334-d4
Casodex-d4
Bicalutamide-d4
(R)-Bicalutamide
CAS Number
113299-40-4
PubChem SID
162038022
PubChem CID
56069

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 56069 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 11.947144  H Acceptors
H Donor LogD (pH = 5.5) 2.7092955 
LogD (pH = 7.4) 2.7092834  Log P 2.7092955 
Molar Refractivity 96.5895 cm3 Polarizability 36.135174 Å3
Polar Surface Area 107.26 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Dichloromethane expand Show data source
Apperance
White Solid expand Show data source
Melting Point
192-194°C expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Target
Androgen Receptor expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals TRC TRC
Selleck Chemicals - S2241 external link
Biological Activity:
(R)-Bicalutamide is an active competitive non-steroidal androgen receptor antagonist with an IC50 of 0.17 μM for MDA 453 cells. (R)-Bicalutamide possesses virtually all activities. (R)-Bicalutamide is the leading antiandrogen. (R)-Bicalutamide is used for the treatment of prostate cancer and breast cancer. (R)-Bicalutamide prevents the activation of the androgen receptor and subsequent upregulation of androgen responsive genes by androgenic hormones. In addition, (R)-bicalutamide accelerates the degradation of the androgen receptor. [1][2][3]References on (R)-Bicalutamide[] PNAS, April 26, 2005, 102:6201–6206[] THE JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277:26321–26326[] J Pharmacol Exp Ther, 2005 February, 312(2): 546–553
Toronto Research Chemicals - B382002 external link
Used as an antiandrogen, antineoplastic (hormonal). (94%d4; 5.7%d3, 0.1%d1, no d0)

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Masiello D et al. J Biol Chem. 2002 Jul 19; 277(29):26321-6.
  • • Tucker, H., et al.: J. Med. Chem., 31, 954 (1988)
  • • Cockshott, I.D., et al.: Eur. Urol., 18, Suppl. 3, 10 (1988)
  • • Cockshott, I., et al.: Br. J. Clin. Pharm., 36, 339 (1988)
  • • McKillop, D., et al.: Xenobiotica, 25, 623 (1988)
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PATENTS

PATENTS

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INTERNET

INTERNET

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