SPIRONOLACTONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1960)
Entry Type: Small molecule
Molecule Category: Parent
ATC: C03DA01
UNII: 27O7W4T232

Structure
InChI Key LXMSZDCAJNLERA-ZHYRCANASA-N
Smile CC(=O)S[C@@H]1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](CC[C@@]34CCC(=O)O4)[C@@H]21
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H32O4S
Molecular Weight 416.58
AlogP 4.85
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 1.0
Polar Surface Area 60.44
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 29.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST Mineralocorticoid receptor antagonist
Primary Target
Mineralocorticoid receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 3000 - - -
Enzyme Hydrolase
- - - -
Enzyme Oxidoreductase
- - - - 27-57
Enzyme Transferase
- - - - 12.48
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
- - - - -0.31-2
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 1
- 5702 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group A Nuclear hormone receptor subfamily 3 group A member 2
3300 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 1
- 1400-6920 - 32.6-864.8 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 2
- 1.6-490 - 2.323-5.012 113
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 3
- 650-4000 - 217.2 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
- 48-670 - 39.4 -
Transcription factor
3300 1.6-490 - 2.323-5.012 113
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - -34.2-103.5
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 82.8-93.9
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 18600 - - 27
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 23600 - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Muscular Dystrophy, Duchenne 3 D020388 ClinicalTrials
Heart Failure, Diastolic 3 D054144 ClinicalTrials
Acne Vulgaris 3 D000152 ClinicalTrials
Acute Kidney Injury 3 D058186 ClinicalTrials
ST Elevation Myocardial Infarction 3 D000072657 ClinicalTrials
Polycystic Kidney, Autosomal Dominant 3 D016891 ClinicalTrials
Atrial Fibrillation 3 D001281 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Non-ST Elevated Myocardial Infarction 3 D000072658 ClinicalTrials
Aortic Valve Stenosis 3 D001024 ClinicalTrials
Arthritis, Rheumatoid 3 D001172 ClinicalTrials
Macular Degeneration 2 D008268 ClinicalTrials
Cerebral Hemorrhage 2 D002543 ClinicalTrials
Cardiomyopathies 2 D009202 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Fatty Liver 2 D005234 ClinicalTrials
Arrhythmogenic Right Ventricular Dysplasia 2 D019571 ClinicalTrials
Polycystic Ovary Syndrome 2 D011085 ClinicalTrials
Hypertension, Pulmonary 2 D006976 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Puberty, Precocious 2 D011629 ClinicalTrials
Diabetes Mellitus 1 D003920 ClinicalTrials
Diabetic Nephropathies 1 D003928 ClinicalTrials
Leukemia, Myeloid, Acute 1 D015470 ClinicalTrials
Leukemia 1 D007938 ClinicalTrials
Melanosis 1 D008548 ClinicalTrials
Non-alcoholic Fatty Liver Disease 1 D065626 ClinicalTrials
Chorioretinitis 1 D002825 ClinicalTrials
Alcoholism 1 D000437 ClinicalTrials
Dry Eye Syndromes 1 D015352 ClinicalTrials

Related Entries

Scaffolds

Mixture

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.37
Metabolism and nutrition disorders
8.85
Nervous system disorders
8.57
Cardiac disorders
7.65
Vascular disorders
6.71
Gastrointestinal disorders
6.2
Renal and urinary disorders
5.49
Investigations
5.3
Skin and subcutaneous tissue disorders
5.13
Injury, poisoning and procedural complications
5.0
Respiratory, thoracic and mediastinal disorders
4.63
Psychiatric disorders
4.28
Musculoskeletal and connective tissue disorders
3.81
Immune system disorders
3.71
Reproductive system and breast disorders
2.39

Cross References

Resources Reference
CAS NUMBER 52-01-7
ChEBI 9241
ChEMBL CHEMBL1393
DrugBank DB00421
DrugCentral 2475
EPA CompTox DTXSID6034186
FDA SRS 27O7W4T232
Human Metabolome Database HMDB14565
Guide to Pharmacology 2875
KEGG C07310
PDB SNL
PharmGKB PA451483
PubChem 5833
SureChEMBL SCHEMBL20939
ZINC ZINC000003861599
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