Spironolactone

Not to be confused with Spirolactone.

Spironolactone
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%[10][11][12]
Protein bindingSpironolactone: 88% (to albumin and AGPTooltip alpha-1-acid glycoprotein)[13]
Canrenone: 99.2% (to albumin)[13]
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[10][11][16][17][18][19][20]
Metabolites7α-TSTooltip 7α-Thiospironolactone, 7α-TMSTooltip 7α-thiomethylspironolactone, 6β-OH-7α-TMSTooltip 6β-hydroxy-7α-thiomethylspironolactone, canrenone, others[10][11][14]
(All three active)[15]
Elimination half-lifeSpironolactone: 1.4 hrs[10]
7α-TMSTooltip 7α-thiomethylspironolactone: 13.8 hours[10]
6β-OH-7α-TMSTooltip 6β-hydroxy-7α-thiomethylspironolactone: 15.0 hrs[10]
Canrenone: 16.5 hours[10]
ExcretionUrine, bile[11]
Identifiers
IUPAC name
  • 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
Chemical and physical data
FormulaC24H32O4S
Molar mass416.58 g·mol−1
3D model (JSmol)
Melting point134 to 135 °C (273 to 275 °F)
SMILES
  • 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
  • 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 Y
  • Key:LXMSZDCAJNLERA-ZHYRCANASA-N Y
  (verify)

Spironolactone, sold under the brand name Aldactone among others, is classed as a diuretic medication.[21] It can be used to treat fluid build-up due to liver disease or kidney disease.[4] It is also used to reduce risk of disease progression, hospitalization and death due to some types of heart failure.[22][23] Other uses include acne and excessive hair growth in women, low blood potassium that does not improve with supplementation, high blood pressure that is difficult to treat and early puberty in boys.[4][24][25][26] It can also be used to block the effects of testosterone as a part of feminizing hormone therapy.[27] Spironolactone is usually available in tablets, taken by mouth, though topical forms are also available.[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]

If taken during pregnancy, some animal studies suggest that spironolactone may affect the development of sex organs in babies.[28] While this has not occurred in the few human studies available,[28][29][30] women who are pregnant or considering pregnancy should discuss spironolactone use with their doctor due to the theoretical risk.[29]

Spironolactone is a steroid that blocks the effects of the hormones aldosterone and, to a lesser degree, testosterone, causing some estrogen-like effects.[31][32][33][4][34] Spironolactone belongs to a class of medications known as potassium-sparing diuretics.[4]

Spironolactone was discovered in 1957, and was introduced in 1959.[35][36][37] It is on the World Health Organization's List of Essential Medicines.[38] It is available as a generic medication.[4] In 2022, it was the 52nd most commonly prescribed medication in the United States, with more than 12 million prescriptions.[39][40] Spironolactone has a history of use in the trans community.[41] Its use continues despite the rise of various accessible alternatives such as bicalutamide and cyproterone acetate with more precise action and less side effects.[31][32]

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  11. ^ 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.
  12. ^ 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.
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  15. ^ 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.
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  21. ^ "Australian Medicines Handbook". amhonline.amh.net.au. Retrieved 12 May 2025.
  22. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).
  23. ^ Li S, Zhang X, Dong M, Gong S, Shang Z, Jia X, et al. (August 2018). "Effects of spironolactone in heart failure with preserved ejection fraction: A meta-analysis of randomized controlled trials". Medicine. 97 (35): e11942. doi:10.1097/MD.0000000000011942. PMC 6392615. PMID 30170387.
  24. ^ Friedman AJ (October 2015). "Spironolactone for Adult Female Acne". Cutis. 96 (4): 216–217. PMID 27141564.
  25. ^ Maizes V (2015). Integrative Women's Health (2 ed.). Oxford University Press. p. 746. ISBN 978-0-19-021480-7.
  26. ^ Sinnott SJ, Tomlinson LA, Root AA, Mathur R, Mansfield KE, Smeeth L, et al. (February 2017). "Comparative effectiveness of fourth-line anti-hypertensive agents in resistant hypertension: A systematic review and meta-analysis" (PDF). European Journal of Preventive Cardiology. 24 (3): 228–238. doi:10.1177/2047487316675194. PMID 27856806.
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  30. ^ Deng N, Zhong J, Deng Z, Chen M, Yan L, Li H, et al. (25 July 2024). "Case report: A pregnant woman accidental treated with spironolactone in mid-gestation". Frontiers in Pharmacology. 15: 1404251. doi:10.3389/fphar.2024.1404251. PMC 11306061. PMID 39119600.
  31. ^ 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.
  32. ^ 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.
  33. ^ Cosgrove B (January 2018). "The Case Against Spironolactone". Modern Trans Hormones. Retrieved 8 July 2024.
  34. ^ 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.
  35. ^ 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.
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  40. ^ "Spironolactone Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  41. ^ Prior JC, Vigna YM, Watson D (1989). "Spironolactone with Physiological Female Steroids for Presurgical Therapy of Male-To-Female Transsexualism". Archives of Sexual Behavior. 18 (1): 49–57. doi:10.1007/BF01579291. PMID 2540730.
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