User:Mr. Ibrahem/Flutamide

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Mr. Ibrahem/Flutamide
Clinical data
Trade namesEulexin, others
Other namesNiftolide; SCH-13521; 4'-Nitro-3'-trifluoromethyl-isobutyranilide
AHFS/Drugs.comMonograph
MedlinePlusa697045
Pregnancy
category
  • D
Routes of
administration		By mouth
Drug classNSAA[1]
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityComplete (>90%)[2]
Protein bindingFlutamide: 94–96%[2]
Hydroxyflutamide: 92–94%[2]
MetabolismLiver (CYP1A2)[8][4]
MetabolitesHydroxyflutamide[3][4]
Elimination half-lifeFlutamide: 5–6 hours[5][4]
Hydroxyflutamide: 8–10 hours[6][7][4][2]
ExcretionUrine (mainly)[2]
Feces (4.2%)[2]
Identifiers
  • 2-Methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
Chemical and physical data
FormulaC11H11F3N2O3
Molar mass276.215 g·mol−1
3D model (JSmol)
Melting point111.5 to 112.5 °C (232.7 to 234.5 °F)
  • CC(C)C(=O)NC1=CC(=C(C=C1)[N+](=O)[O-])C(F)(F)F
  • InChI=1S/C11H11F3N2O3/c1-6(2)10(17)15-7-3-4-9(16(18)19)8(5-7)11(12,13)14/h3-6H,1-2H3,(H,15,17) checkY
  • Key:MKXKFYHWDHIYRV-UHFFFAOYSA-N checkY
  (verify)

Flutamide, sold under the brand name Eulexin among others, is a medication primarily used to treat prostate cancer.[10] For prostate cancer it is used together with a luteinizing hormone-releasing hormone (LHRH).[1] It is also used for unwanted hair growth and hair loss in polycystic ovarian syndrome.[9] It is taken by mouth three times per day.[11]

Common side effects in men include hot flashes, sexual dysfunction, breast enlargement, and nausea.[1] In women, it is generally better tolerated with only dry skin being common.[12] Other side effects may include liver problems, QT prolongation, and sunburns.[1][10] Use in pregnancy may harm the baby.[1] It is a nonsteroidal antiandrogen (NSA) that works by selectively blocking the androgen receptor (AR).[1]

Flutamide was described in 1967 and was introduced for medical use in 1983.[13] It was approved in the United States in 1989.[1] 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.[10] In the United Kingdom 4 weeks of medication costs the NHS about £110 as of 2021.[10] This amount in the United States costs about 85 USD.[15] Use has frequently been replaced by others NSAAs, namely bicalutamide, as it works better, has less side effects, and is easier to take.[5][16]

References[edit]

  1. ^ a b c d e f g h i "Flutamide Monograph for Professionals". Drugs.com. Archived from the original on 11 October 2018. Retrieved 14 December 2021.
  2. ^ a b c d e f "Flutamide Capsules USP". Archived from the original on 2020-08-12. Retrieved 2021-10-05.
  3. ^ Diamanti-Kandarakis E (September 1999). "Current aspects of antiandrogen therapy in women". Curr. Pharm. Des. 5 (9): 707–23. PMID 10495361. Archived from the original on 2020-02-27. Retrieved 2021-10-05.
  4. ^ a b c d Bruce A. Chabner; Dan L. Longo (8 November 2010). Cancer Chemotherapy and Biotherapy: Principles and Practice. Lippincott Williams & Wilkins. pp. 679–. ISBN 978-1-60547-431-1. Archived from the original on 14 September 2021. Retrieved 5 October 2021.
  5. ^ a b James Leonard Gulley (2011). Prostate Cancer. Demos Medical Publishing. p. 504. ISBN 978-1-935281-91-7. Archived from the original on 2021-12-15. Retrieved 2021-12-14.
  6. ^ 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 5 October 2021.
  7. ^ Louis J Denis; Keith Griffiths; Amir V Kaisary; Gerald P Murphy (1 March 1999). Textbook of Prostate Cancer: Pathology, Diagnosis and Treatment: Pathology, Diagnosis and Treatment. CRC Press. pp. 279–280. ISBN 978-1-85317-422-3. Archived from the original on 27 July 2020. Retrieved 5 October 2021.
  8. ^ Richard A. Lehne (2013). Pharmacology for Nursing Care. Elsevier Health Sciences. pp. 1297–. ISBN 978-1-4377-3582-6. Archived from the original on 2020-07-27. Retrieved 2021-10-05.
  9. ^ a b "Polycystic Ovary Syndrome - Treatment - NHS Choices". Nhs.uk. 2011-10-17. Archived from the original on 2011-11-06. Retrieved 2013-01-04.
  10. ^ a b c d e BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 992. ISBN 978-0857114105.
  11. ^ Ismaila A Mungadi; Hyacinth N Mbibu; Ehab Eltahawy; Abdullahi Abdulwahab-Ahmed (30 November 2013). Manual of Medical Treatment in Urology. JP Medical Ltd. pp. 120–. ISBN 978-93-5090-844-0. Archived from the original on 14 September 2021. Retrieved 5 October 2021.
  12. ^ Fishman, Sarah L.; Paliou, Maria; Poretsky, Leonid; Hembree, Wylie C. (2019). "Endocrine Care of Transgender Adults". Contemporary Endocrinology. pp. 143–163. doi:10.1007/978-3-030-05683-4_8. ISSN 2523-3785. The use of these agents as antiandrogens in transgender patients has been limited by concerns of hepatotoxicity. However, at low doses, these agents have shown to be both well tolerated and effective when used for the treatment of hirsutism [57].
  13. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 515. ISBN 9783527607495. Archived from the original on 2020-07-27. Retrieved 2021-10-05.
  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. ^ "Flutamide Prices and Flutamide Coupons - GoodRx". GoodRx. Retrieved 14 December 2021.
  16. ^ Lutz Moser (1 January 2008). Controversies in the Treatment of Prostate Cancer. Karger Medical and Scientific Publishers. pp. 41–42. ISBN 978-3-8055-8524-8. Archived from the original on 27 July 2020. Retrieved 5 October 2021. Latest studies suggest that [flutamide] also reduces adrenal and ovarian androgen synthesis [58,59].
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