Spironolactone

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

Not to be confused with Spirolactone.

Spironolactone
Clinical data
Pronunciation/ˌspaɪroʊnoʊˈlæktoʊn/ SPY-roh-noh-LAK-tone, /ˌspɪəroʊnoʊˈlæktoʊn/ SPEER-oh-noh-LAK-tone
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
  • AU: B3
Routes of
administration		By mouth, topical
Drug classAntimineralocorticoid; Steroidal antiandrogen
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
Pharmacokinetic data
Bioavailability60–90%
Protein bindingSpironolactone: 88% (to albumin and AGPTooltip alpha-1-acid glycoprotein)
Canrenone: 99.2% (to albumin)
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
Metabolites7α-TSTooltip 7α-Thiospironolactone, 7α-TMSTooltip 7α-thiomethylspironolactone, 6β-OH-7α-TMSTooltip 6β-hydroxy-7α-thiomethylspironolactone, canrenone, others
(All three active)
Elimination half-lifeSpironolactone: 1.4 hrs
7α-TMSTooltip 7α-thiomethylspironolactone: 13.8 hours
6β-OH-7α-TMSTooltip 6β-hydroxy-7α-thiomethylspironolactone: 15.0 hrs
Canrenone: 16.5 hours
ExcretionUrine, bile
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
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 Y
  • Key:LXMSZDCAJNLERA-ZHYRCANASA-N Y
  (verify)

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

Spironolactone was discovered in 1957, and was introduced in 1959. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2021, it was the 54th most commonly prescribed medication in the United States, with more than 12 million prescriptions.

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