Bicalutamide

Bicalutamide
Clinical data


Pronunciation	Bicalutamide: bye-KA-loo-TA-mide Casodex: kay-SOH-dex
Trade names	Casodex, Cosudex, Calutide, Calumid, Kalumid, others
AHFS/Drugs.com	Monograph
MedlinePlus	a697047
License data	US FDA: Bicalutamide
Pregnancy category	AU: D US: X (Contraindicated)
Routes of administration	By mouth
Drug class	Non-steroidal antiandrogen
ATC code	L02BB03 (WHO)
Legal status
Legal status	℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Well-absorbed; absolute bioavailability unknown
Protein binding	Racemate: 96.1% (R)-Isomer: 99.6% (Mainly to albumin)
Metabolism	Hepatic (extensively): • Hydroxylation (CYP3A4) • Glucuronidation (UGT1A9)
Metabolites	• Bicalutamide glucuronide • Hydroxybicalutamide • Hydroxybicalutamide gluc. (All inactive)
Biological half-life	Acute: 5.8 days Chronic: 7–10 days
Excretion	Feces: 43% Urine: 34%
Identifiers
IUPAC name (RS)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide
Synonyms	ICI-176,334
CAS Number	90357-06-5^Y 113299-40-4 ((R)-isomer)
PubChem (CID)	2375
IUPHAR/BPS	2863
DrugBank	DB01128^Y
ChemSpider	2284^Y
UNII	A0Z3NAU9DP^Y
KEGG	D00961^N
ChEBI	CHEBI:3090^N
ChEMBL	CHEMBL409^N
PDB ligand ID	198 (PDBe, RCSB PDB)
ECHA InfoCard	100.126.100
Chemical and physical data
Formula	C₁₈H₁₄F₄N₂O₄S
Molar mass	430.373 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
Melting point	191 to 193 °C (376 to 379 °F)
Solubility in water	0.005 mg/mL (20 °C)
SMILES O=C(Nc1cc(c(C#N)cc1)C(F)(F)F)C(O)(C)CS(=O)(=O)c2ccc(F)cc2
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)^Y Key:LKJPYSCBVHEWIU-UHFFFAOYSA-N^Y
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Bicalutamide, sold under the brand name Casodex among others, is an antiandrogen that is used primarily in the treatment of prostate cancer. It is used alone or together with surgical or medical castration for this indication, and is able to slow the course of the disease and extend life. Bicalutamide is also used to treat excessive hair growth in women,early-onset puberty in boys, as a component of hormone therapy for transgender women, and in the treatment of other androgen-dependent conditions.

Bicalutamide is a non-steroidal antiandrogen (NSAA) and acts as a selective antagonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It does not lower androgen levels, instead acting purely by preventing androgens from mediating their effects in the body. Bicalutamide is taken by mouth. It is well-absorbed, and its absorption is not affected by food. The drug has a long terminal half-life of 6 to 10 days. It crosses the blood–brain barrier. The major side effects of bicalutamide in men are gynecomastia (breast development), breast tenderness, and feminization in general, whereas the drug produces few side effects and is very well-tolerated in women. Bicalutamide can cause elevated liver enzymes in around 1% of people, and has been associated with a few cases of liver damage as well as lung toxicity. Although the risk is low, monitoring of liver enzymes is recommended during treatment.

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