Bicalutamide

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 advanced prostate cancer. Bicalutamide may also be used to treat excessive hair growth in women, as a component of feminizing hormone therapy for transgender women, to treat early puberty in boys, and to prevent overly long-lasting erections in men. It is taken by mouth.

Bicalutamide
Clinical data
Pronunciation Bicalutamide:
/bkəˈltəmd/
bye-kə-LOO-tə-myde
Casodex:
/ˈksdɛks/
KAY-soh-deks
Trade names Casodex, others
Synonyms ICI-176,334; ZD-176,334
AHFS/Drugs.com Monograph
MedlinePlus a697047
License data
Pregnancy
category
  • AU: D
  • US: X (Contraindicated)
    Routes of
    administration
    By mouth
    Drug class Nonsteroidal antiandrogen
    ATC code
    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)
    Elimination half-life Acute: 5.8 days
    Chronic: 7–10 days
    Excretion Feces: 43%
    Urine: 34%
    Identifiers
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    PDB ligand
    ECHA InfoCard 100.126.100
    Chemical and physical data
    Formula C18H14F4N2O4S
    Molar mass 430.373 g/mol
    3D model (JSmol)
    Chirality Racemic mixture (of (R)- and (S)-enantiomers)
    Melting point 191 to 193 °C (376 to 379 °F) (experimental)
    Boiling point 650 °C (1,202 °F) (predicted)
    Solubility in water 0.005 mg/mL (20 °C)
      (verify)

    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 (FDA). Use during pregnancy may harm the baby. Bicalutamide causes elevated liver enzymes in around 1% of people. Rarely, it has been associated with cases of liver damage, lung toxicity, and sensitivity to light. Although the risk of adverse liver changes is small, monitoring of liver function is recommended during treatment.

    Bicalutamide is a member of the nonsteroidal antiandrogen (NSAA) group of medications. It works by blocking the androgen receptor (AR), the biological target of the androgen sex hormones testosterone and dihydrotestosterone (DHT). It does not lower androgen levels. The medication can have some estrogen-like effects in men. Bicalutamide is well-absorbed, and its absorption is not affected by food. The elimination half-life of the medication is around one week. It is believed to cross the blood–brain barrier and affect both the body and brain.

    Bicalutamide was patented in 1982 and approved for medical use in 1995. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Bicalutamide is available as a generic medication. The wholesale cost in the developing world is about US$7.07 to US$144.22 per month. In the United States it costs about US$10 and above per month. The drug is sold in more than 80 countries, including most developed countries. It is the most widely used antiandrogen in the treatment of prostate cancer, and has been prescribed to millions of men with the disease.

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