Nilutamide
Chemical compound / From Wikipedia, the free encyclopedia
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Nilutamide, sold under the brand names Nilandron and Anandron, is a nonsteroidal antiandrogen (NSAA) which is used in the treatment of prostate cancer.[7][8][9][10][11][12] It has also been studied as a component of feminizing hormone therapy for transgender women and to treat acne and seborrhea in women.[13][14][15][16] It is taken by mouth.[4]
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Pronunciation | nye-LOO-tah-mide[1] |
Trade names | Nilandron, Anandron |
Other names | RU-23908 |
AHFS/Drugs.com | Monograph |
MedlinePlus | a697044 |
Routes of administration | By mouth[2] |
Drug class | Nonsteroidal antiandrogen |
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Bioavailability | Good[2] |
Protein binding | 80–84%[4] |
Metabolism | Liver (CYP2C19, FMOTooltip flavin-containing monooxygenase)[2][4] |
Metabolites | At least 5, some active[4][5] |
Elimination half-life | Mean: 56 hours (~2 days)[6] Range: 23–87 hours[6] |
Excretion | Urine: 62%[2][4] Feces: <10%[2][4] |
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ECHA InfoCard | 100.153.268 |
Chemical and physical data | |
Formula | C12H10F3N3O4 |
Molar mass | 317.224 g·mol−1 |
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Melting point | 149 °C (300 °F) |
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Side effects in men include breast tenderness and enlargement, feminization, sexual dysfunction, and hot flashes.[17][18][19][20] Nausea, vomiting, visual disturbances, alcohol intolerance, elevated liver enzymes, and lung disease can occur in both sexes.[20][21][18][22][23][24] Rarely, nilutamide can cause respiratory failure and liver damage.[17][20] These unfavorable side effects, along with a number of associated cases of death, have limited the use of nilutamide.[12][25][26]
Nilutamide acts as a selective antagonist of the androgen receptor (AR), preventing the effects of androgens like testosterone and dihydrotestosterone (DHT) in the body.[27][13] Because most prostate cancer cells rely on these hormones for growth and survival, nilutamide can slow the progression of prostate cancer and extend life in men with the disease.[13]
Nilutamide was discovered in 1977 and was first introduced for medical use in 1987.[8][28][29][6] It became available in the United States in 1996.[30][31][32] The drug has largely been replaced by newer and improved NSAAs, namely bicalutamide and enzalutamide, due to their better efficacy, tolerability, and safety, and is now rarely used.[33]
It is on the World Health Organization's List of Essential Medicines.[34]