Spironolactone
Steroidal antiandrogen and antimineralocorticoid / From Wikipedia, the free encyclopedia
Dear Wikiwand AI, let's keep it short by simply answering these key questions:
Can you list the top facts and stats about Spironolactone?
Summarize this article for a 10 year old
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]
Clinical data | |
---|---|
Pronunciation | /ˌspaɪroʊnoʊˈlæktoʊn/ SPY-roh-noh-LAK-tone,[1] /ˌspɪəroʊnoʊˈlæktoʊn/ SPEER-oh-noh-LAK-tone[2] |
Trade names | Aldactone, others |
Other names | SC-9420; NSC-150339; 7α-Acetylthiospirolactone; 7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682627 |
License data | |
Pregnancy category |
|
Routes of administration | By mouth,[4] topical[5] |
Drug class | Antimineralocorticoid; Steroidal antiandrogen |
ATC code | |
Legal status | |
Legal status | |
Pharmacokinetic data | |
Bioavailability | 60–90%[11][12][13] |
Protein binding | Spironolactone: 88% (to albumin and AGPTooltip alpha-1-acid glycoprotein)[14] Canrenone: 99.2% (to albumin)[14] |
Metabolism | Liver, 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][15][16][17][18][19] |
Metabolites | 7α-TSTooltip 7α-Thiospironolactone, 7α-TMSTooltip 7α-thiomethylspironolactone, 6β-OH-7α-TMSTooltip 6β-hydroxy-7α-thiomethylspironolactone, canrenone, others[11][12][20] (All three active)[21] |
Elimination half-life | Spironolactone: 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] |
Excretion | Urine, bile[12] |
Identifiers | |
| |
CAS Number |
|
PubChem CID | |
IUPHAR/BPS | |
DrugBank |
|
ChemSpider |
|
UNII | |
KEGG |
|
ChEBI | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.000.122 |
Chemical and physical data | |
Formula | C24H32O4S |
Molar mass | 416.58 g·mol−1 |
3D model (JSmol) | |
Melting point | 134 to 135 °C (273 to 275 °F) |
| |
| |
(verify) |
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?]