Casodex

Bicalutamide

Clinical data
Pronunciation	Bicalutamide: /baɪkəˈluːtəmaɪd/ bye-kə-LOO-tə-myde Casodex: /ˈkeɪsoʊdɛks/ KAY-soh-deks
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	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	Well-absorbed; absolute bioavailability unknown
Protein binding	Racemate: 96.1% (R)-Isomer: 99.6% (Mainly to albumin)
Metabolism	Liver (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
PubChem CID	2375
IUPHAR/BPS	2863
DrugBank	DB01128 Y
ChemSpider	2284 Y
UNII	A0Z3NAU9DP
KEGG	D00961 N
ChEBI	CHEBI:3090 N
ChEMBL	CHEMBL409 N
PDB ligand	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
NY (what is this?)

Bicalutamide, sold under the brand name Casodex among others, is an antiandrogen medication that is primarily used to treat prostate cancer. It is typically used together with a gonadotropin-releasing hormone (GnRH) analogue or surgical removal of the testicles to treat metastatic prostate cancer. Bicalutamide may also be used to treat excessive hair growth in women, as a component of hormone therapy for transgender women, to prevent priapism, and to treat early puberty in boys. It is taken by mouth.

Common side effects in men include breast enlargement, breast tenderness, and hot flashes. Other side effects in men include feminization and sexual dysfunction. While the medication appears to produce few side effects in women, its use in women is not recommended by the Food and Drug Administration. Use during pregnancy may harm the baby. Bicalutamide causes elevated liver enzymes in around 1% of people. It has been associated with rare cases of liver damage and lung toxicity. Although the risk of liver damage is small, monitoring of liver enzymes is recommended during treatment.

Bicalutamide is a member of the non-steroidal antiandrogen (NSAA) group of medications. It works by blocking the androgen receptor (AR), the biological target of the androgen sex hormones, such as testosterone and dihydrotestosterone (DHT). It does not lower androgen levels. Bicalutamide is well-absorbed, and its absorption is not affected by food. The terminal half-life of the medication is about six days. It is believed to cross the blood–brain barrier and have an effect on both the body and brain.