User:Mr. Ibrahem/Nilutamide

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Mr. Ibrahem/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 (NSAA)[3]
Legal status
Legal status
  • 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
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 medication used to treat prostate cancer.[7] It has also been used as a component of feminizing hormone therapy for transgender women.[10] It is taken by mouth[7]

Common side effects may include hot flushes, poor ability to see in darkness, nausea, constipation, trouble sleeping, and breat enlargement.[8] Other side effects may include sexual dysfunction, osteoporosis, alcohol intolerance[8][7] Rarely, it can cause pneumonitis and liver damage.[7] These unfavorable side effects have limited it use.[11]

Nilutamide is a nonsteroidal antiandrogen (NSAA) which acts as a selective antagonist of the androgen receptor (AR), preventing the effects of androgens.[3] As prostate cancer rely on these hormones for growth and survival, it can slow the progression of the disease.[7]

Nilutamide was discovered in 1977 and was approved for medical use in 1987.[12][13] It was approved in the United States in 1996.[7] It is on the World Health Organization's List of Essential Medicines as an alternative to bicalutamide.[14] It is available as a generic medication.[15] In the United States 30 tablets of 150 mg costs about 1,600 USD as of 2021.[15]

References[edit]

  1. ^ "Nilutamide - LiverTox". National Institutes of Health. Archived from the original on 24 September 2018. Retrieved 24 September 2018. In large registration clinical trials, ALT elevations occurred in 2% to 33% of patients during nilutamide therapy. The elevations were usually mild, asymptomatic and transient, rarely requiring drug discontinuation. In rare instances, clinically apparent acute liver injury has occurred during nilutamide therapy, but the number of published cases are few, and the agent appears to be far less hepatotoxic than flutamide.
  2. ^ a b c d e Michael C. Perry; Donald C. Doll; Carl E. Freter (30 July 2012). Perry's The Chemotherapy Source Book. Lippincott Williams & Wilkins. pp. 711–. ISBN 978-1-4698-0343-2.
  3. ^ a b "DailyMed - NILUTAMIDE tablet". dailymed.nlm.nih.gov. Archived from the original on 24 March 2021. Retrieved 13 November 2021.
  4. ^ a b c d e Thomas L. Lemke; David A. Williams (24 January 2012). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1373–. ISBN 978-1-60913-345-0. Archived from the original on 14 September 2021. Retrieved 4 October 2021.
  5. ^ Bruce A. Chabner; Dan L. Longo (8 November 2010). Cancer Chemotherapy and Biotherapy: Principles and Practice. Lippincott Williams & Wilkins. pp. 680–. ISBN 978-1-60547-431-1. Archived from the original on 27 July 2020. Retrieved 4 October 2021.
  6. ^ a b Kolvenbag, Geert J. C. M.; Furr, Barrington J. A. (2009). "Nonsteroidal Antiandrogens". In V. Craig Jordan; Barrington J. A. Furr (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. ^ a b c d e f g "Nilutamide Monograph for Professionals". Drugs.com. Archived from the original on 4 March 2016. Retrieved 13 November 2021.
  8. ^ a b c Richard A. Lehne (2013). Pharmacology for Nursing Care. Elsevier Health Sciences. pp. 1297–. ISBN 978-1-4377-3582-6. Archived from the original on 27 July 2020. Retrieved 4 October 2021.
  9. ^ "Nilutamide (Nilandron) Use During Pregnancy". Archived from the original on 28 October 2020. Retrieved 4 October 2021.
  10. ^ <Baudewijntje P.C. Kreukels; Thomas D. Steensma; Annelou L.C. de Vries (1 July 2013). Gender Dysphoria and Disorders of Sex Development: Progress in Care and Knowledge. Springer Science & Business Media. pp. 280–. ISBN 978-1-4614-7441-8. Archived from the original on 14 September 2021. Retrieved 4 October 2021.
  11. ^ Vincent T. DeVita; Theodore S. Lawrence; Steven A. Rosenberg (18 March 2016). Prostate and Other Genitourinary Cancers: Cancer: Principles & Practice of Oncology. Wolters Kluwer Health. pp. 1006–. ISBN 978-1-4963-5421-1.
  12. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 873–. ISBN 978-1-4757-2085-3.
  13. ^ János Fischer; Christian Klein; Wayne E. Childers (16 April 2018). Successful Drug Discovery. Wiley. pp. 98–. ISBN 978-3-527-80868-7. Archived from the original on 28 October 2021. Retrieved 4 October 2021.
  14. ^ 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.
  15. ^ a b "Nilutamide Prices, Coupons & Savings Tips - GoodRx". GoodRx. Archived from the original on 8 November 2016. Retrieved 13 November 2021.
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