Structure via PubChem · Public domain (PubChem)
nilutamide
Sign in to saveAlso known as Nilandron®, 5,5-Dimethyl-3-(alpha,alpha,alpha-trifluoro-4-nitro-m-tolyl)hydantoin, Nilutamida, Nilutamidum
Nilutamide, sold under the brand names Nilandron and Anandron, is a nonsteroidal antiandrogen (NSAA) which is used in the treatment of prostate cancer. It has also been studied as a component of feminizing hormone therapy for transgender women and to treat acne and seborrhea in women. It is taken by mouth.
Chemical data
- Formula
- C12H10F3N3O4
- Molecular weight
- 317.22 g/mol
- IUPAC name
- 5,5-dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
- SMILES
- CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C
- InChIKey
- XWXYUMMDTVBTOU-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 95.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1996
- Admin. routes
- oral
- Indications
- neoplasm, prostate adenocarcinoma, prostate cancer, metastatic prostate cancer
via ChEMBL · EBI
Research
341 papers- Nilutamide.2012
- Nilutamide: an antiandrogen for the treatment of prostate cancer.The Annals of pharmacotherapy · 1997
- Pharmacokinetics and metabolism of nilutamide.Urology · 1991
- Nilutamide. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in prostate cancer.Drugs & aging · 1993
- Efficacy and Safety of Nilutamide in Patients with Metastatic Prostate Cancer who Underwent Orchiectomy: A Systematic Review and Metaanalysis.Current clinical pharmacology · 2019
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 317.06234
- Has use
- medication
Show 9 more facts
- Commons category
- Nilutamide
- chemical formula
- C₁₂H₁₀F₃N₃O₄
- subject has role
- antiandrogen
- medical condition treated
- prostate cancer
- canonical SMILES
- CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C
- World Health Organisation international non-proprietary name
- nilutamide
- defined daily dose
- 0.3
- physically interacts with
- androgen receptor
- legal status (medicine)
- boxed warning
Sources (7)
via Wikidata · CC0
~11 min read
Encyclopedic overview
20 sectionsContents
- Medical uses
- Prostate cancer
- Transgender hormone therapy
- Skin conditions
- Available forms
- Side effects
- Pharmacology
- Pharmacodynamics
- Antiandrogenic activity
- Cytochrome P450 inhibition
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Generic names
- Brand names
- Availability
- Research
- References
- Further reading
Nilutamide, sold under the brand names Nilandron and Anandron, is a nonsteroidal antiandrogen (NSAA) which is used in the treatment of prostate cancer. It has also been studied as a component of feminizing hormone therapy for transgender women and to treat acne and seborrhea in women. It is taken by mouth.
Side effects in men include breast tenderness and enlargement, feminization, sexual dysfunction, and hot flashes. Nausea, vomiting, visual disturbances, alcohol intolerance, elevated liver enzymes, and lung disease can occur in both sexes. Rarely, nilutamide can cause respiratory failure and liver damage. These unfavorable side effects, along with a number of associated cases of death, have limited the use of nilutamide.
Excerpted from Wikipedia’s “nilutamide” article, available under the CC BY-SA 4.0 licence.