Back سبيرونولاكتون Arabic اسپیرونولاکتون AZB Espironolactona Catalan Spironolacton Welsh Spironolacton German Σπειρονολακτόνη Greek Spironolaktono Esperanto Espironolactona Spanish Espironolaktona Basque اسپیرونولاکتون Persian

Spironolactone

Not to be confused with Spirolactone.

Spironolactone
Skeletal formula of spironolactone
Ball-and-stick model of the spironolactone molecule
Clinical data
Pronunciation/ˌspaɪroʊnoʊˈlæktoʊn/ SPY-roh-noh-LAK-tone,[1] /ˌspɪəroʊnoʊˈlæktoʊn/ SPEER-oh-noh-LAK-tone[2]
Trade namesAldactone, others
Other namesSC-9420; NSC-150339; 7α-Acetylthiospirolactone; 7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone
AHFS/Drugs.comMonograph
MedlinePlusa682627
License data
Pregnancy
category
Routes of
administration		By mouth,[4] topical[5]
Drug classAntimineralocorticoid; Steroidal antiandrogen
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60–90%[11][12][13]
Protein bindingSpironolactone: 88% (to albumin and AGPTooltip alpha-1-acid glycoprotein)[14]
Canrenone: 99.2% (to albumin)[14]
MetabolismLiver, others:
• Deacetylation via CESTooltip carboxylesterase
• S-Oxygenation via FOMTooltip flavin-containing monooxygenase
• S-Methylation via TMTTooltip thiol S-methyltransferase
• Dethioacetylation
• Hydroxylation via CYP3A4
• Lactone hydrolysis via PON3[11][12][17][18][19][20][21]
Metabolites7α-TSTooltip 7α-Thiospironolactone, 7α-TMSTooltip 7α-thiomethylspironolactone, 6β-OH-7α-TMSTooltip 6β-hydroxy-7α-thiomethylspironolactone, canrenone, others[11][12][15]
(All three active)[16]
Elimination half-lifeSpironolactone: 1.4 hrs[11]
7α-TMSTooltip 7α-thiomethylspironolactone: 13.8 hours[11]
6β-OH-7α-TMSTooltip 6β-hydroxy-7α-thiomethylspironolactone: 15.0 hrs[11]
Canrenone: 16.5 hours[11]
ExcretionUrine, bile[12]
Identifiers
  • S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.122 Edit this at Wikidata
Chemical and physical data
FormulaC24H32O4S
Molar mass416.58 g·mol−1
3D model (JSmol)
Melting point134 to 135 °C (273 to 275 °F)
  • O=C5O[C@@]4([C@@]3([C@H]([C@@H]2[C@H](SC(=O)C)C/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)CC4)C)CC5
  • InChI=1S/C24H32O4S/c1-14(25)29-19-13-15-12-16(26)4-8-22(15,2)17-5-9-23(3)18(21(17)19)6-10-24(23)11-7-20(27)28-24/h12,17-19,21H,4-11,13H2,1-3H3/t17-,18-,19+,21+,22-,23-,24+/m0/s1 checkY
  • Key:LXMSZDCAJNLERA-ZHYRCANASA-N checkY
  (verify)
Spironolactone 25 mg

Spironolactone, sold under the brand name Aldactone among others, is a diuretic medication primarily used to treat fluid build-up due to heart failure, liver scarring, or kidney disease.[4] It is also used in the treatment of high blood pressure, and low blood potassium that does not improve with supplementation, early puberty in boys, acne and excessive hair growth in women.[4][22][23] Spironolactone is taken by mouth.[4]

Common side effects include electrolyte abnormalities, particularly high blood potassium, nausea, vomiting, headache, rashes, and a decreased desire for sex.[4] In those with liver or kidney problems, extra care should be taken.[4] Spironolactone has not been well studied in pregnancy and should not be used to treat high blood pressure of pregnancy.[3] It is also a steroid that blocks the effects of the hormones aldosterone and, to a lesser degree, testosterone, causing some estrogen-like effects.[24][unreliable source?][25][26][unreliable medical source?][4][27] Spironolactone belongs to a class of medications known as potassium-sparing diuretics.[4]

Spironolactone was discovered in 1957, and was introduced in 1959.[28][29][30] It is on the World Health Organization's List of Essential Medicines.[31] It is available as a generic medication.[4] In 2021, it was the 54th most commonly prescribed medication in the United States, with more than 12 million prescriptions.[32][33] Spironolactone has a history of use in the trans community due to ease of access at a time when feminizing hormone therapy was less commonly accepted.[citation needed] Its use continues despite the rise of various accessible alternatives such as bicalutamide and cyproterone acetate with more precise action and less side effects.[24][25][26][unreliable medical source?]

  1. ^ Loughlin KR, Generali JA (2006). The Guide to Off-label Prescription Drugs: New Uses for FDA-approved Prescription Drugs. Simon and Schuster. pp. 131–. ISBN 978-0-7432-8667-1. Archived from the original on 7 October 2022. Retrieved 6 November 2016.
  2. ^ Clark MA, Harvey RA, Finkel R, Rey JA, Whalen K (15 December 2011). Pharmacology. Lippincott Williams & Wilkins. pp. 286, 337. ISBN 978-1-4511-1314-3. Archived from the original on 7 October 2022. Retrieved 6 November 2016.
  3. ^ a b "Spironolactone Pregnancy and Breastfeeding Warnings". The American Society of Health-System Pharmacists. Archived from the original on 2 December 2015. Retrieved 29 November 2015.
  4. ^ a b c d e f g h i "Spironolactone". The American Society of Health-System Pharmacists. Archived from the original on 16 November 2015. Retrieved 24 October 2015.
  5. ^ Cite error: The named reference FARIDDiamanti-Kandarakis2009 was invoked but never defined (see the help page).
  6. ^ "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.
  7. ^ "Aldactone 25 mg Film-Coated TabletsSummary of Product Characteristics (SmPC)". (emc). 3 February 2022. Archived from the original on 6 October 2022. Retrieved 2 August 2023.
  8. ^ Cite error: The named reference Aldactone label was invoked but never defined (see the help page).
  9. ^ "Qaialdo EPAR". European Medicines Agency (EMA). 25 July 2023. Archived from the original on 27 July 2023. Retrieved 2 August 2023.
  10. ^ "Qaialdo". Union Register of medicinal products. 31 May 2023. Archived from the original on 6 June 2023. Retrieved 6 June 2023.
  11. ^ a b c d e f g Cite error: The named reference pmid15947888 was invoked but never defined (see the help page).
  12. ^ a b c d Maron BA, Leopold JA (September 2008). "Mineralocorticoid receptor antagonists and endothelial function". Current Opinion in Investigational Drugs. 9 (9): 963–9. PMC 2967484. PMID 18729003.
  13. ^ Carone L, Oxberry SG, Twycross R, Charlesworth S, Mihalyo M, Wilcock A (February 2017). "Spironolactone". Journal of Pain and Symptom Management. 53 (2): 288–292. doi:10.1016/j.jpainsymman.2016.12.320. PMID 28024992.
  14. ^ a b Cite error: The named reference TakamuraMaruyama1997 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference SzaszBudvari-Barany1990 was invoked but never defined (see the help page).
  16. ^ McDonagh TA, Gardner RS, Clark AL, Dargie H (14 July 2011). Oxford Textbook of Heart Failure. OUP Oxford. pp. 403–. ISBN 978-0-19-957772-9. Archived from the original on 27 March 2017.
  17. ^ Cite error: The named reference Parkinson2001 was invoked but never defined (see the help page).
  18. ^ Cite error: The named reference Klaassen2007 was invoked but never defined (see the help page).
  19. ^ Cite error: The named reference pmid7895608 was invoked but never defined (see the help page).
  20. ^ Cite error: The named reference BlackElliott2006 was invoked but never defined (see the help page).
  21. ^ Cite error: The named reference pmid14579013 was invoked but never defined (see the help page).
  22. ^ Friedman AJ (October 2015). "Spironolactone for Adult Female Acne". Cutis. 96 (4): 216–7. PMID 27141564.
  23. ^ Maizes V (2015). Integrative Women's Health (2 ed.). Oxford University Press. p. 746. ISBN 978-0-19-021480-7.
  24. ^ a b Burinkul S, Panyakhamlerd K, Suwan A, Tuntiviriyapun P, Wainipitapong S (July 2021). "Anti-Androgenic Effects Comparison Between Cyproterone Acetate and Spironolactone in Transgender Women: A Randomized Controlled Trial". The Journal of Sexual Medicine. 18 (7): 1299–1307. doi:10.1016/j.jsxm.2021.05.003. PMID 34274044.
  25. ^ a b Sehgal I (2023). "Review of adult gender transition medications: mechanisms, efficacy measures, and pharmacogenomic considerations". Frontiers in Endocrinology. 14: 1184024. doi:10.3389/fendo.2023.1184024. PMC 10355117. PMID 37476490.
  26. ^ a b Cosgrove B (January 2018). "The Case Against Spironolactone". Modern Trans Hormones. Retrieved 8 July 2024.
  27. ^ Deedwania PC (30 January 2014). Drug & Device Selection in Heart Failure. JP Medical Ltd. pp. 47–. ISBN 978-93-5090-723-8. Archived from the original on 7 October 2022. Retrieved 5 July 2017.
  28. ^ Ottow E, Weinmann H (9 July 2008). Nuclear Receptors As Drug Targets. John Wiley & Sons. p. 410. ISBN 978-3-527-62330-3. Archived from the original on 21 June 2013. Retrieved 28 May 2012.
  29. ^ Wermuth CG (24 July 2008). The Practice of Medicinal Chemistry. Academic Press. p. 34. ISBN 978-0-12-374194-3. Archived from the original on 21 June 2013. Retrieved 27 May 2012.
  30. ^ Sittig M (1988). Pharmaceutical Manufacturing Encyclopedia. William Andrew. p. 1385. ISBN 978-0-8155-1144-1. Archived from the original on 20 June 2013. Retrieved 27 May 2012.
  31. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  32. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  33. ^ "Spironolactone - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.
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