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.
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2D Structure
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1960))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
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
International Nonproprietary Names Click here for help
INN number INN
987 spironolactone
Synonyms Click here for help
Aldactone® | spiractin | spirotone
Database Links Click here for help
BindingDB Ligand 50228080
CAS Registry No. 52-01-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1393
DrugBank Ligand DB00421
DrugCentral Ligand 2475
GtoPdb PubChem SID 135651065
PubChem CID 5833
RCSB PDB Ligand SNL
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SynPHARM 78981 (in complex with Mineralocorticoid receptor)
Wikipedia Spironolactone

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Tocris
Spironolactone
Cat. No. 2968