spironolactone   

GtoPdb Ligand ID: 2875

Synonyms: Aldactone® | spiractin | spirotone
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
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
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
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
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
INN number INN
987 spironolactone
Synonyms
Aldactone® | spiractin | spirotone
Database Links
BindingDB Ligand 50228080
CAS Registry No. 52-01-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1393
DrugBank Ligand DB00421
DrugCentral Ligand 2475
GtoPdb PubChem SID 135651065
NURSA Ligand 10.1621/HQ7UWR1R9B
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