Spironolactone

Spironolactone
Clinical data


Pronunciation	spy-ROW-no-LAK-tone or speer-OH-no-LAK-tone
Trade names	Aldactone, Spiractin, Verospiron, many others; combinations: Aldactazide (+HCTZ), Aldactide (+HFMZ), Aldactazine (+altizide), others
AHFS/Drugs.com	Monograph
MedlinePlus	a682627
Pregnancy category	AU: B3 US: C (Risk not ruled out)
Routes of administration	By mouth,topical
ATC code	C03DA01 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	80–90%
Protein binding	Spironolactone: 88% (to albumin and AGP equivalently) Canrenone: 99.2% (to albumin)
Metabolism	Liver (deacetylation, dethiolation, and thiomethylation)
Metabolites	7α-TMS, 6β-OH-7α-TMS, canrenone, others (All three active)
Biological half-life	Spironolactone: 1.4 hours 7α-TMS: 13.8 hours 6β-OH-7α-TMS: 15.0 hours Canrenone: 16.5 hours
Excretion	Urine, bile
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
Synonyms	SC-9420; 7α-Acetylthio-17α-hydroxy-3-oxopregn-4-ene-21-carboxylic acid γ-lactone
CAS Number	52-01-7^Y
PubChem CID	5833
IUPHAR/BPS	2875
DrugBank	DB00421^Y
ChemSpider	5628^Y
UNII	27O7W4T232
KEGG	D00443^Y
ChEBI	CHEBI:9241^Y
ChEMBL	CHEMBL1393^Y
ECHA InfoCard	100.000.122
Chemical and physical data
Formula	C₂₄H₃₂O₄S
Molar mass	416.574 g/mol
3D model (Jmol)	Interactive image
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

Spironolactone, marketed 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-onset puberty, and acne and excessive hair growth in women. It is also used for hormone therapy in transgender women. Spironolactone is taken by mouth.

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 effects similar to those of the hormone progesterone. Spironolactone belongs to a class of medications known as potassium-sparing diuretics.

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Wikipedia