User:Mr. Ibrahem/Dutasteride

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Mr. Ibrahem/Dutasteride
Clinical data
Trade namesAvodart, others; Combodart, Duodart (with tamsulosin)
Other namesGG-745; GI-198745; GI-198745X; N-[2,5-Bis(trifluoromethyl)phenyl]-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide
AHFS/Drugs.comMonograph
MedlinePlusa603001
License data
Pregnancy
category
  • Not to be used during pregnancy
Routes of
administration		By mouth
Drug class5α-Reductase inhibitor
Legal status
Legal status
Pharmacokinetic data
Bioavailability60%[1]
Protein binding99%[1]
MetabolismLiver (CYP3A4)[1]
Metabolites• 4'-Hydroxydutasteride[1]
• 6'-Hydroxydutasteride[1]
• 1,2-Dihydrodutasteride[1]
(All three active)[1]
Elimination half-life4–5 weeks[2][3]
ExcretionFeces: 40% (metabolites)[1]
Urine: 5% (unchanged)[1]
Identifiers
  • (1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
Chemical and physical data
FormulaC27H30F6N2O2
Molar mass528.539 g·mol−1
3D model (JSmol)
  • FC(F)(F)c1cc(c(cc1)C(F)(F)F)NC(=O)[C@@H]3[C@]2(CC[C@H]4[C@H]([C@@H]2CC3)CC[C@H]5NC(=O)\C=C/[C@]45C)C
  • InChI=1S/C27H30F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1 checkY
  • Key:JWJOTENAMICLJG-QWBYCMEYSA-N checkY
  (verify)

Dutasteride, sold under the brand name Avodart among others, is a medication primarily used to treat the symptoms of an enlarged prostate.[4][6] A few months may be required before benefits occur.[6] It is also used for scalp hair loss in men and as a part of hormone therapy in transgender women.[7][8] It is taken by mouth.[4][9]

Common side effects include sexual problems, breast tenderness, and breast enlargement.[4] Other side effects include an increased risk of certain forms of prostate cancer, depression, and angioedema.[4][6] Exposure during pregnancy, including use by the partner of a pregnant women may result in harm to the baby.[4][6] Dutasteride is a 5α-reductase inhibitor, and hence is a type of antiandrogen.[3] It works by decreasing the production of dihydrotestosterone (DHT), an androgen sex hormone.[10][4]

Dutasteride was patented in 1993 by GlaxoSmithKline and was approved for medical use in 2001.[11][4] It is available as a generic medication.[6] A month supply in the United Kingdom costs the NHS about £12 as of 2019.[6] In the United States, the wholesale cost of this amount is about $6.66.[12] In 2017, it was the 276th most commonly prescribed medication in the United States, with more than one million prescriptions.[13][14]

References[edit]

  1. ^ a b c d e f g h i Thomas L. Lemke; David A. Williams (2008). Foye's Principles of Medicinal Chemistry. Lippincott Williams & Wilkins. pp. 1286–1287. ISBN 978-0-7817-6879-5. Archived from the original on 2017-09-08. Retrieved 2017-12-06.
  2. ^ Jacqueline Burchum; Laura Rosenthal (2 December 2014). Lehne's Pharmacology for Nursing Care. Elsevier Health Sciences. pp. 803–. ISBN 978-0-323-34026-7. Archived from the original on 23 December 2016. Retrieved 27 October 2016.
  3. ^ a b Ulrike Blume-Peytavi; David A. Whiting; Ralph M. Trüeb (26 June 2008). Hair Growth and Disorders. Springer Science & Business Media. pp. 182, 369. ISBN 978-3-540-46911-7. Archived from the original on 11 January 2020. Retrieved 10 December 2016.
  4. ^ a b c d e f g h "Dutasteride Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 4 July 2019. Retrieved 18 March 2019.
  5. ^ "WHOCC - ATC/DDD Index". www.whocc.no. Archived from the original on 5 March 2021. Retrieved 7 September 2020.
  6. ^ a b c d e f British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 769. ISBN 9780857113382.
  7. ^ Jerry Shapiro; Nina Otberg (17 April 2015). Hair Loss and Restoration, Second Edition. CRC Press. pp. 39–. ISBN 978-1-4822-3199-1. Archived from the original on 11 January 2020. Retrieved 27 October 2016.
  8. ^ Wesp LM, Deutsch MB (2017). "Hormonal and Surgical Treatment Options for Transgender Women and Transfeminine Spectrum Persons". Psychiatr. Clin. North Am. 40 (1): 99–111. doi:10.1016/j.psc.2016.10.006. PMID 28159148.
  9. ^ Wu C, Kapoor A (2013). "Dutasteride for the treatment of benign prostatic hyperplasia". Expert Opin Pharmacother. 14 (10): 1399–408. doi:10.1517/14656566.2013.797965. PMID 23750593.
  10. ^ Aggarwal S, Thareja S, Verma A, Bhardwaj TR, Kumar M (February 2010). "An overview on 5alpha-reductase inhibitors". Steroids. 75 (2): 109–53. doi:10.1016/j.steroids.2009.10.005. PMID 19879888.
  11. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 483. ISBN 9783527607495. Archived from the original on 2019-03-01. Retrieved 2019-03-01.
  12. ^ "NADAC as of 2019-02-27". Centers for Medicare and Medicaid Services. Archived from the original on 2019-03-06. Retrieved 3 March 2019.
  13. ^ "The Top 300 of 2020". ClinCalc. Archived from the original on 12 February 2021. Retrieved 11 April 2020.
  14. ^ "Dutasteride - Drug Usage Statistics". ClinCalc. Archived from the original on 6 February 2020. Retrieved 11 April 2020.
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