Bicalutamide

Title: Bicalutamide
CAS Registry Number: 90357-06-5
CAS Name: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
Additional Names: 4-cyano-3-trifluoromethyl-N-(3-p-fluorophenylsulfonyl-2-hydroxy-2-methylpropionyl)aniline; (±)-4¢-cyano-a,a,a-trifluoro-3-[(p-fluorophenyl)sulfonyl]-2-methyl-m-lactotoluidide
Manufacturers' Codes: ICI-176334
Trademarks: Casodex (AstraZeneca)
Molecular Formula: C18H14F4N2O4S
Molecular Weight: 430.37
Percent Composition: C 50.23%, H 3.28%, F 17.66%, N 6.51%, O 14.87%, S 7.45%
Literature References: Non-steroidal peripherally active antiandrogen. Prepn: H. Tucker, EP 100172; idem, US 4636505 (1984, 1987 both to ICI); and structure-activity: H. Tucker et al., J. Med. Chem. 31, 954 (1988). Resolution and activity of enantiomers: H. Tucker, G. J. Chesterson, ibid. 885. Pharmacokinetics: I. D. Cockshott et al., Eur. Urol. 18, Suppl. 3, 10 (1990). Clinical trials in prostate cancer: G. Lunglmayr, Horm. Res. 32, Suppl. 1, 77 (1989); D. W. W. Newling, Eur. Urol. 18 Suppl. 3, 18 (1990). Review of pharmacology: B. J. A. Furr in Hormonal Therapy of Prostatic Diseases: Basic and Clinical Aspects, M. Motta, M. Serio, Eds. (Mediocom Europe, Milan, 1987) 148-161.
Properties: Crystals from a 1:1 (v/v) mix of ethyl acetate and petroleum ether, mp 191-193°.
Melting point: mp 191-193°
Therap-Cat: Antiandrogen; antineoplastic (hormonal).
Keywords: Antiandrogen; Antineoplastic (Hormonal); Antiandrogens.
Bicozamycin Bicuculline Bidisomide Bietamiverine Bietanautine

Bicalutamide
Bicalutamide.svg
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Systematic (IUPAC) name
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
Clinical data
Trade names Casodex
AHFS/Drugs.com monograph
MedlinePlus a697047
Pregnancy cat. X (US)
Legal status Prescription only
Routes Oral
Pharmacokinetic data
Bioavailability well absorbed
Protein binding 96%
Metabolism hepatic
Half-life 5.8 days
Identifiers
CAS number 90357-06-5 YesY
ATC code L02BB03
PubChem CID 2375
IUPHAR ligand 2863
DrugBank DB01128
ChemSpider 2284 YesY
UNII A0Z3NAU9DP YesY
KEGG D00961 N
ChEMBL CHEMBL63560 N
Chemical data
Formula C18H14F4N2O4S 
Mol. mass 430.373 g/mol
 N (what is this?)  (verify)

Bicalutamide (marketed as Casodex, Cosudex, Calutide, Kalumid) is an oral non-steroidal anti-androgen used in the treatment of prostate cancer[1][2][3] and hirsutism.[4] 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.[5]