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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H32O4S
Molecular Weight 416.573
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SPIRONOLACTONE

SMILES

CC(=O)S[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]45CCC(=O)O5)[C@H]13

InChI

InChIKey=LXMSZDCAJNLERA-ZHYRCANASA-N
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

HIDE SMILES / InChI

Molecular Formula C24H32O4S
Molecular Weight 416.573
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Spironolactone is a synthetic 17-lactone steroid which is a renal competitive aldosterone antagonist in a class of pharmaceuticals called potassium-sparing diuretics. On its own, spironolactone is only a weak diuretic, but it can be combined with other diuretics. Due to its anti-androgen effect, it can also be used to treat hirsutism, and is a common component in hormone therapy for male-to-female transgendered people. Spironolactone inhibits the effect of aldosterone by competing for intracellular aldosterone receptor in the distal tubule cells. This increases the secretion of water and sodium, while decreasing the excretion of potassium. Spironolactone has a fairly slow onset of action, taking several days to develop and similarly the effect diminishes slowly. Spironolactone is a specific pharmacologic antagonist of aldosterone, acting primarily through competitive binding of receptors at the aldosterone-dependent sodium-potassium exchange site in the distal convoluted renal tubule. Spironolactone causes increased amounts of sodium and water to be excreted, while potassium is retained. Spironolactone acts both as a diuretic and as an antihypertensive drug by this mechanism. It may be given alone or with other diuretic agents which act more proximally in the renal tubule. Aldosterone interacts with a cytoplasmic mineralocorticoid receptor to enhance the expression of the Na+, K+-ATPase and the Na+ channel involved in a Na+ K+ transport in the distal tubule . Spironolactone bind to this mineralcorticoid receptor, blocking the actions of aldosterone on gene expression. Aldosterone is a hormone; its primary function is to retain sodium and excrete potassium in the kidneys. Spironolactone is used primarily to treat low-renin hypertension, hypokalemia, and Conn's syndrome.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
11.0 nM [IC50]
120.0 nM [IC50]
650.0 nM [IC50]
1.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ALDACTONE
Primary
ALDACTONE
Primary
ALDACTONE

Cmax

ValueDoseCo-administeredAnalytePopulation
47.4 ng/mL
100 mg single, oral
SPIRONOLACTONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
150.41 ng × h/mL
100 mg single, oral
SPIRONOLACTONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.37 h
100 mg single, oral
SPIRONOLACTONE plasma
Homo sapiens
1.4 h
unknown
SPIRONOLACTONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
unknown
SPIRONOLACTONE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Edema 25 to 200 mg/day orally in 1 or 2 divided doses. Usual Adult Dose for Hypertension 25 to 200 mg/day orally in 1 or 2 divided doses. Usual Adult Dose for Hypokalemia 25 to 200 mg/day orally in 1 or 2 divided doses. Usual Adult Dose for Primary Hyperaldosteronism Diagnosis 100 to 400 mg/day orally in 1 or 2 divided doses. Usual Adult Dose for Hirsutism 50 to 200 mg/day orally in 1 or 2 divided doses. Usual Adult Dose for Congestive Heart Failure 25 mg/day orally. Increase or decrease based on response and evidence of hyperkalemia. Usual Adult Dose for Primary Hyperaldosteronism Initial dose: 100 mg orally once a day. This dosage may be divided into two daily doses, and increased as tolerated every two to three days to a maximum recommended total daily dose of 400 mg.
Route of Administration: Oral
In Vitro Use Guide
Spironolactone (10 uM) abrogated MR agonist aldosterone-increased I (CaL) density in adult rat ventricular myocytes
Substance Class Chemical
Record UNII
27O7W4T232
Record Status Validated (UNII)
Record Version