Nilutamide

Nilutamide
Clinical data
Pronunciationnye-LOO-tah-mide[1]
Trade namesNilandron, Anandron
Other namesRU-23908
AHFS/Drugs.comMonograph
MedlinePlusa697044
Routes of
administration		By mouth[2]
Drug classNonsteroidal antiandrogen
ATC code
Legal status
Legal status
  • US: WARNING[3]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityGood[2]
Protein binding80–84%[4]
MetabolismLiver (CYP2C19, FMOTooltip flavin-containing monooxygenase)[2][4]
MetabolitesAt least 5, some active[4][5]
Elimination half-lifeMean: 56 hours (~2 days)[6]
Range: 23–87 hours[6]
ExcretionUrine: 62%[2][4]
Feces: <10%[2][4]
Identifiers
  • 5,5-Dimethyl-3-[4-nitro-3-(trifluoromethyl)phenyl]imidazolidine-2,4-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.153.268 Edit this at Wikidata
Chemical and physical data
FormulaC12H10F3N3O4
Molar mass317.224 g·mol−1
3D model (JSmol)
Melting point149 °C (300 °F)
  • CC1(C(=O)N(C(=O)N1)C2=CC(=C(C=C2)[N+](=O)[O-])C(F)(F)F)C
  • InChI=1S/C12H10F3N3O4/c1-11(2)9(19)17(10(20)16-11)6-3-4-8(18(21)22)7(5-6)12(13,14)15/h3-5H,1-2H3,(H,16,20) checkY
  • Key:XWXYUMMDTVBTOU-UHFFFAOYSA-N checkY
  (verify)

Nilutamide, sold under the brand names Nilandron and Anandron, is a nonsteroidal antiandrogen (NSAA) which is used in the treatment of prostate cancer.[8][9][10][11][12][13] It has also been studied as a component of feminizing hormone therapy for transgender women and to treat acne and seborrhea in women.[14][15][16][17] It is taken by mouth.[4]

Side effects in men include breast tenderness and enlargement, feminization, sexual dysfunction, and hot flashes.[18][19][20][21] Nausea, vomiting, visual disturbances, alcohol intolerance, elevated liver enzymes, and lung disease can occur in both sexes.[21][22][19][23][24][25] Rarely, nilutamide can cause respiratory failure and liver damage.[18][21] These unfavorable side effects, along with a number of associated cases of death, have limited the use of nilutamide.[13][26][27]

Nilutamide acts as a selective antagonist of the androgen receptor (AR), preventing the effects of androgens like testosterone and dihydrotestosterone (DHT) in the body.[28][14] 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.[14]

Nilutamide was discovered in 1977 and was first introduced for medical use in 1987.[9][29][30][6] It became available in the United States in 1996.[31][32][33] 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.[34]

It is on the World Health Organization's List of Essential Medicines.[35]

  1. ^ Cite error: The named reference LiverTox was invoked but never defined (see the help page).
  2. ^ a b c d e Perry MC, Doll DC, Freter CE (30 July 2012). Perry's The Chemotherapy Source Book. Lippincott Williams & Wilkins. pp. 711–. ISBN 978-1-4698-0343-2.
  3. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  4. ^ a b c d e f Lemke TL, Williams DA (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1373–. ISBN 978-1-60913-345-0.
  5. ^ Cite error: The named reference ChabnerLongo2010 was invoked but never defined (see the help page).
  6. ^ a b c Kolvenbag GJ, Furr BJ (2009). "Nonsteroidal Antiandrogens". In Jordan VC, Furr HJ (eds.). Hormone Therapy in Breast and Prostate Cancer. Humana Press. pp. 347–368. doi:10.1007/978-1-59259-152-7_16. ISBN 978-1-60761-471-5. Although the t1/2 of nilutamide is h (mean 56 h) (39), suggesting that once-daily dosing would be appropriate, a three times per day regimen has been employed in most clinical trials.
  7. ^ "Nilutamide (Nilandron) Use During Pregnancy". Archived from the original on 28 October 2020. Retrieved 20 July 2016.
  8. ^ "NILANDRON® (nilutamide)" (PDF). Archived (PDF) from the original on 30 March 2021. Retrieved 25 September 2018.
  9. ^ a b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 873–. ISBN 978-1-4757-2085-3.
  10. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 737–. ISBN 978-3-88763-075-1.
  11. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 199–. ISBN 978-94-011-4439-1.
  12. ^ "Nilutamide". Archived from the original on 2 December 2020. Retrieved 14 November 2017.
  13. ^ a b Denis LJ, Griffiths K, Kaisary AV, Murphy GP (1 March 1999). Textbook of Prostate Cancer: Pathology, Diagnosis and Treatment: Pathology, Diagnosis and Treatment. CRC Press. pp. 280–. ISBN 978-1-85317-422-3. Archived from the original on 10 January 2023. Retrieved 21 February 2016.
  14. ^ a b c Cite error: The named reference Denis2012a was invoked but never defined (see the help page).
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  18. ^ a b Dole EJ, Holdsworth MT (January 1997). "Nilutamide: an antiandrogen for the treatment of prostate cancer". The Annals of Pharmacotherapy. 31 (1): 65–75. doi:10.1177/106002809703100112. PMID 8997470. S2CID 20347526.
  19. ^ a b Cite error: The named reference Dart2004 was invoked but never defined (see the help page).
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  21. ^ a b c Cite error: The named reference Lehne2013 was invoked but never defined (see the help page).
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  25. ^ Boarder MR, Newby D, Navti P (25 March 2010). Pharmacology for Pharmacy and the Health Sciences: A Patient-centred Approach. OUP Oxford. pp. 632–. ISBN 978-0-19-955982-4. Archived from the original on 6 July 2024. Retrieved 12 October 2016.
  26. ^ DeVita VT, Lawrence TS, Rosenberg SA, eds. (18 March 2016). Prostate and Other Genitourinary Cancers: Cancer: Principles & Practice of Oncology. Wolters Kluwer Health. pp. 1006–. ISBN 978-1-4963-5421-1.
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  35. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.