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bicalutamide

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bicalutamide

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Also known as ZD7054, ICI 176334

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 (mPC). To a lesser extent, it is used at high doses for locally advanced prostate cancer (LAPC) as a monotherapy without castration. Bicalutamide was also previously used as monotherapy to treat localized prostate cancer (LPC), but authorization for this use was withdrawn following unfavorable trial f

Key facts

Drug.Verifiedfields
verified
Drug.Watchedfields
verified
Drug.verifiedrevid
459978482
Drug.image
Bicalutamide.svg
Drug.image_class
skin-invert-image
Drug.width
250
Drug.image2
Bicalutamide 3D ball.png
Drug.image_class2
bg-transparent
Drug.width2
250
Drug.pronounce
Bicalutamide:• •
Drug.tradename
Casodex, Calutex, others
Drug.MedlinePlus
a697047
Drug.DailyMedID
Bicalutamide
Drug.licence_US
Bicalutamide
Drug.pregnancy_AU
D
Drug.routes_of_administration
By mouth
Drug.class
Nonsteroidal antiandrogen
Drug.ATC_prefix
L02

via Wikipedia infobox

Chemical data

Formula
C18H14F4N2O4S
Molecular weight
430.4 g/mol
IUPAC name
N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methylpropanamide
SMILES
CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
InChIKey
LKJPYSCBVHEWIU-UHFFFAOYSA-N
XLogP
2.3
Polar surface area
116 Ų
H-bond donors
2
H-bond acceptors
9
Formal charge
0

via PubChem

Wikidata facts

Mass
430.061041
Has use
medication
Show 10 more facts
chemical formula
C₁₈H₁₄F₄N₂O₄S
MCN code
2930.90.72
World Health Organisation international non-proprietary name
bicalutamide
medical condition treated
prostate cancer
canonical SMILES
CC(CS(=O)(=O)C1=CC=C(C=C1)F)(C(=O)NC2=CC(=C(C=C2)C#N)C(F)(F)F)O
topic's main category
Category:Bicalutamide
Commons category
Bicalutamide
defined daily dose
50
subject has role
essential medicine
physically interacts with
androgen receptor
Sources (6)

via Wikidata · CC0

~46 min read

Encyclopedic overview

27 sections
Contents
  • Medical uses
  • Available forms
  • Contraindications
  • Side effects
  • Comparison
  • Overdose
  • Interactions
  • Pharmacology
  • Pharmacodynamics
  • Antiandrogenic activity
  • Other activities
  • Pharmacokinetics
  • Chemistry
  • Analogues
  • Synthesis
  • History
  • Society and culture
  • Generic names
  • Brand names
  • Cost and generics
  • Sales and usage
  • Regulation
  • Research
  • Veterinary use
  • See also
  • References
  • Further reading

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 (mPC). To a lesser extent, it is used at high doses for locally advanced prostate cancer (LAPC) as a monotherapy without castration. Bicalutamide was also previously used as monotherapy to treat localized prostate cancer (LPC), but authorization for this use was withdrawn following unfavorable trial findings. Besides prostate cancer, bicalutamide is limitedly used in the treatment of excessive hair growth and scalp hair loss in women, as a puberty blocker and component of feminizing hormone therapy for transgender girls and women, to treat gonadotropin-independent early puberty in boys, and to prevent overly long-lasting erections in men. It is taken by mouth.

Common side effects of bicalutamide in men include breast growth, breast tenderness, and hot flashes. Other side effects in men include feminization and sexual dysfunction. Some side effects like breast changes and feminization are minimal when combined with castration. While the medication appears to produce few side effects in women, its use in women is not explicitly approved by the Food and Drug Administration (FDA) at this time. Use during pregnancy may harm the baby. In men with early prostate cancer, bicalutamide monotherapy has been found to increase the likelihood of death from causes other than prostate cancer. Bicalutamide produces abnormal liver changes necessitating discontinuation in around 1% of people. Rarely, it has been associated with cases of serious liver damage, serious lung toxicity, and sensitivity to light. Although the risk of adverse liver changes is small, monitoring of liver function is recommended during treatment.

Excerpted from Wikipedia’s “bicalutamide” article, available under the CC BY-SA 4.0 licence.

Gallery (3)