Nilutamide

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Nilutamide
Nilutamide.svg
Systematic (IUPAC) name
5,5-dimethyl-3-(4-nitro-3-(trifluoromethyl)phenyl)imidazolidine-2,4-dione
Clinical data
Trade names Nilandron
AHFS/Drugs.com monograph
MedlinePlus a697044
Legal status
  • ℞ (Prescription only)
Routes of
administration		 Oral
Pharmacokinetic data
Biological half-life ~56 hours[1]
Identifiers
CAS Number 63612-50-0 YesY
ATC code L02BB02 (WHO)
PubChem CID: 4493
IUPHAR/BPS 2864
DrugBank DB00665 YesY
ChemSpider 4337 YesY
UNII 51G6I8B902 YesY
KEGG D00965 YesY
ChEBI CHEBI:7573 YesY
ChEMBL CHEMBL1274 YesY
Synonyms RU-23908
Chemical data
Formula C12H10F3N3O4
Molecular mass 317.221 g/mol
  • O=C2N(c1ccc([N+]([O-])=O)c(c1)C(F)(F)F)C(=O)C(N2)(C)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) YesY
  • Key:XWXYUMMDTVBTOU-UHFFFAOYSA-N YesY
  (verify)

Nilutamide (INN, USAN, BAN) (brand names Nilandron (US), Anandron (CA)) is a synthetic, non-steroidal, pure antiandrogen used in the treatment of advanced-stage (metastatic) prostate cancer.[2][3][4] It was developed by Roussel, introduced in 1987,[2] and was the second non-steroidal antiandrogen to be marketed after flutamide.[4] Nilutamide acts as a potent and selective competitive silent antagonist of the androgen receptor (AR), which prevents testosterone and other androgens from activating the AR.[5] Because most prostate cancer cells rely on activation of the AR for growth and survival, nilutamide can extend life in men with prostate cancer.[5]

Nilutamide is used in prostate cancer in combination with a GnRH analogue at a dosage of 300 mg daily for the first 4 weeks of treatment, and 150 mg once daily thereafter.[6][1] It is not indicated as a monotherapy in prostate cancer.[1] Nilutamide has a half-life of approximately two days, which allows for once-daily administration.[4] In addition to prostate cancer, nilutamide has also been studied in and used as a component of hormone replacement therapy in trans women.[5][7]

General side effects of non-steroidal antiandrogens, including nilutamide, include gynecomastia, breast pain/tenderness, hot flashes, depression, fatigue, and sexual dysfunction.[8][9] In addition, relative to other non-steroidal antiandrogens, nilutamide has been uniquely associated with mild and reversible visual disturbances (31%), a disulfiram-like[8] alcohol intolerance (19%), and interstitial pneumonitis (1–2%[10][11]) (which can progress to pulmonary fibrosis[12]), and has a higher incidence of nausea (27%) and vomiting than other non-steroidal antiandrogens.[1][13][4] There is also a risk of hepatoxicity with nilutamide, though occurrence is very rare and the risk is significantly less than with flutamide.[14][15] The unique adverse effects of nilutamide, and especially its risk of interstitial pneumonitis, have limited its clinical use relative to other non-steroidal antiandrogens.[1][4] From a safety standpoint, bicalutamide is clinically preferred over both nilutamide (due to interstitial pneumonitis) and flutamide (due to hepatotoxicity) in regards to choice of non-steroidal antiandrogen.[11]

Like other non-steroidal antiandrogens such as flutamide and bicalutamide, nilutamide, without concomitant GnRH analogue therapy, increases serum androgen (by two-fold in the case of testosterone), estrogen, and prolactin levels due to inhibition of AR-mediated suppression of steroidogenesis via negative feedback on the hypothalamic-pituitary-gonadal axis.[5] As such, though nilutamide is still highly effective as an antiandrogen as a monotherapy, it is given in combination with a GnRH analogue such as leuprorelin in prostate cancer to suppress androgen concentrations to castrate levels in order to attain maximal androgen blockade (MAB).[5]

Like flutamide and bicalutamide, nilutamide is able to cross the blood-brain-barrier and has central antiandrogen actions.[16]

See also

References

<templatestyles src="Reflist/styles.css" />

Cite error: Invalid <references> tag; parameter "group" is allowed only.

Use <references />, or <references group="..." />


  1. ↑ 1.0 1.1 1.2 1.3 1.4 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ 2.0 2.1 Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ 4.0 4.1 4.2 4.3 4.4 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 5.2 5.3 5.4 Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ 8.0 8.1 Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ 11.0 11.1 Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
Retrieved from "https://infogalactic.com/w/index.php?title=Nilutamide&oldid=2580224"