Structure via PubChem · Public domain (PubChem)
bicalutamide
Sign in to saveAlso 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was also previously used as monotherapy to treat localized prostate cancer (LPC), but authorization for this use was withdrawn following unfavorable trial f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
Research
2,268 papers- Rezvilutamide versus bicalutamide in combination with androgen-deprivation therapy in patients with high-volume, metastatic, hormone-sensitive prostate cancer (CHART): a randomised, open-label, phase 3 trial.The Lancet. Oncology · 2022
- Bicalutamide and the new perspectives for female pattern hair loss treatment: What dermatologists should know.Journal of cosmetic dermatology · 2022
- Bicalutamide: clinical pharmacokinetics and metabolism.Clinical pharmacokinetics · 2004
- [Bicalutamide].Nihon rinsho. Japanese journal of clinical medicine · 2000
- Bicalutamide dosages used in the treatment of prostate cancer.The Prostate · 1999
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- 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 sectionsContents
- 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)
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