Spironolactone

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Spironolactone

Systematic (IUPAC) name
7α-acetylthio-3-oxo-17α-pregn-4-ene-21,17-carbolactone or 17-hydroxy-7α-mercapto-3-oxo-17α-pregn-4-ene-21-carboxylic acid, γ-lactone acetate
Clinical data
Trade names	Aldactone
AHFS/Drugs.com	monograph
MedlinePlus	a682627
Pregnancy cat.	B3 (AU) C (US)
Legal status	POM (UK) ℞-only (US)
Routes	Oral
Pharmacokinetic data
Protein binding	90%+[1]
Metabolism	Hepatic
Half-life	1.3-2 hours
Excretion	Urine, bile
Identifiers
CAS number	52-01-7
ATC code	C03DA01
PubChem	CID 5833
IUPHAR ligand	2875
DrugBank	DB00421
ChemSpider	5628
UNII	27O7W4T232
KEGG	D00443
ChEBI	CHEBI:9241
ChEMBL	CHEMBL1393
Chemical data
Formula	C24H32O4S
Mol. mass	416.574 g/mol
SMILES[show]
InChI[show]
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Spironolactone (INN, BAN, USAN) (pronounced /ˌspaɪrɵnɵˈlæktoʊn/),^[2] commonly referred to simply as "spiro",^[3][4] and marketed primarily under the brand name Aldactone in most countries, is a synthetic, steroidal antimineralocorticoid agent with additional antiandrogen and weak progestogen properties, as well as some indirect estrogen and glucocorticoid effects, which is used primarily as a diuretic and antihypertensive, but also for the purpose of reducing elevated or unwanted androgen activity in the body.^[5] It acts predominantly as a competitive antagonist of the aldosterone (or mineralocorticoid) receptor, and belongs to a class of pharmaceutical drugs known as potassium-sparing diuretics.
Spironolactone is a relatively old drug, having been introduced clinically in 1959.^[6][7] It has been predicted that spironolactone will be superseded in cardiovascular conditions (e.g., heart failure and hypertension) by the newer agents such as the structurally related compound eplerenone, which is also an aldosterone antagonist but is selective and lacks many of the actions and side effects of spironolactone, and as such is much more tolerable in comparison.^[8] However, spironolactone is still far more widely used than eplerenone. Spironolactone nonetheless still finds frequent use as an antiandrogen.