Structure via PubChem · Public domain (PubChem)
flutamide
Sign in to saveAlso known as alpha,alpha,alpha-trifluoro-2-methyl-4'-nitro-m-propionotoluidide, 4'-nitro-3'-trifluoromethylisobutyranilide, FTA, NFBA, niftolide
Flutamide, sold under the brand name Eulexin among others, is a nonsteroidal antiandrogen (NSAA) which is used primarily to treat prostate cancer. It is also used in the treatment of androgen-dependent conditions like acne, excessive hair growth, and high androgen levels in women. It is taken by mouth, usually three times per day.
Key facts
- Drug.ChEMBL
- 806
- Drug.ChEBI
- 5132
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 461102563
- Drug.IUPAC_name
- 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
- Drug.image
- Flutamide.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 225
- Drug.image2
- Flutamide molecule ball.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 225
- Drug.tradename
- Eulexin, others
- Drug.MedlinePlus
- a697045
- Drug.pregnancy_category
- D
- Drug.legal_status
- Rx-only
- Drug.routes_of_administration
- By mouth
- Drug.class
- Nonsteroidal antiandrogen
- Drug.bioavailability
- Complete (>90%)
via Wikipedia infobox
Chemical data
- Formula
- C11H11F3N2O3
- Molecular weight
- 276.21 g/mol
- IUPAC name
- 2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
- SMILES
- CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F
- InChIKey
- MKXKFYHWDHIYRV-UHFFFAOYSA-N
- XLogP
- 3.3
- Polar surface area
- 74.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
4,021 papersvia PubMed
Wikidata facts
- Mass
- 276.072177
Show 5 more facts
- chemical formula
- C₁₁H₁₁F₃N₂O₃
- canonical SMILES
- CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F
- defined daily dose
- 0.75
- Commons category
- Flutamide
- MCN code
- 2924.29.62
Sources (9)
via Wikidata · CC0
~28 min read
Article
35 sectionsContents
- Medical uses
- Prostate cancer
- Skin and hair conditions
- Acne and seborrhea
- Excessive hair growth
- Scalp hair loss
- Other uses
- Available forms
- Side effects
- Gynecomastia
- Diarrhea
- Rare reactions
- Liver toxicity
- Others
- Birth defects
- Pharmacology
- Pharmacodynamics
- Antiandrogenic activity
- CYP17A1 inhibition
- Other activities
- Pharmacokinetics
- Chemistry
- Synthesis
- History
- Society and culture
- Generic names
- Brand names
- Availability
- Research
- Prostate cancer
- Enlarged prostate
- Breast cancer
- Psychiatric disorders
- References
- Further reading
Flutamide, sold under the brand name Eulexin among others, is a nonsteroidal antiandrogen (NSAA) which is used primarily to treat prostate cancer. It is also used in the treatment of androgen-dependent conditions like acne, excessive hair growth, and high androgen levels in women. It is taken by mouth, usually three times per day.
Side effects in men include breast tenderness and enlargement, feminization, sexual dysfunction, and hot flashes. Conversely, the medication has fewer side effects and is better-tolerated in women with the most common side effect being dry skin. Diarrhea and elevated liver enzymes can occur in both sexes. Rarely, flutamide can cause liver damage, lung disease, sensitivity to light, elevated methemoglobin, elevated sulfhemoglobin, and deficient neutrophils. Numerous cases of liver failure and death have been reported, which has limited the use of flutamide.