spironolactone   Click here for help

GtoPdb Ligand ID: 2875

Synonyms: Aldactone® | spiractin | spirotone
Approved drug PDB Ligand
spironolactone is an approved drug (FDA (1960))
Compound class: Synthetic organic
Comment: Spironolactone is an orally active, potassium-sparing diuretic, which works by antagonising the effects of aldosterone at renal mineralocorticoid receptors.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: spironolactone

spironolactone is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 4
Hydrogen bond donors 0
Rotatable bonds 2
Topological polar surface area 85.74
Molecular weight 416.2
XLogP 3.44
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES CC(=O)SC1CC2=CC(=O)CCC2(C2C1C1CCC3(C1(CC2)C)CCC(=O)O3)C
Isomeric SMILES CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]2[C@@H]1[C@@H]1CC[C@]3([C@]1(CC2)C)CCC(=O)O3)C
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
InChI Key LXMSZDCAJNLERA-ZHYRCANASA-N
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of low-renin hypertension, hypokalemia and Conn's syndrome. CaroSpir® is an oral suspension of spironolactone that received US FDA approval in August 2017, developed for patients who can't swallow tablets or have difficulty swallowing. CaroSpir® is indicated for the treatment of Class III-IV heart failure (to manage edema and reduce hospitalisations), and as an adjunct to anti-hypertensive medications.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Spironolactone has multiple actions including antimineralocorticoid and antiandrogenic activities, as well as estrogenic and progestogenic activities. The most relevant action is as an aldosterone antagonist at the mineralocorticoid receptor in the cortical collecting duct of renal nephrons, an action which decreases renal sodium and water reabsorption (sparing potassium excretion) to increase fluid loss. Spironolactone is also a direct androgen receptor antagonist, and this action underlies its therapeutic efficacy in androgen-dependent conditions (acne and hirsutism for example) and its utility during hormone therapy for transgender women. Activity as a weak 17β-hydroxysteroid dehydrogenase 2 inhibitor may underlie the altered testosterone:estradiol ratio and resulting gynecomastia that is associated with spironolactone administration.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com