PIOGLITAZONE

Search structure
Synonyms:
Status: Approved (1999)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A10BG03
UNII: X4OV71U42S

Structure
InChI Key HYAFETHFCAUJAY-UHFFFAOYSA-N
Smile CCc1ccc(CCOc2ccc(CC3SC(=O)NC3=O)cc2)nc1
InChI
InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H20N2O3S
Molecular Weight 356.45
AlogP 3.16
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 68.29
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 25.0

Pharmacology

Primary Target
Peroxisome proliferator-activated receptor-γ
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- - - - 38
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 61
Enzyme Hydrolase
- - - -
Enzyme Lyase
- 114 - - -
Enzyme Oxidoreductase
- 298-298 - 199.4-500 -
Enzyme Phosphatase Protein Phosphatase Tyrosine protein phosphatase
- 650-220000 - - 33.8-85
Enzyme Transferase
- - - - 10.3
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Free fatty acid receptor
812830.52 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 1
6680-100000 1150 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 2
43000 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 3
88-17700 720-22000 871 62-1230.27 67.5-82.6
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 21.9-70
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 260-400 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 49500 - - -
Unclassified protein
- 1000 - 370 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Atherosclerosis 3 D050197 ClinicalTrials
Insulin Resistance 3 D007333 ClinicalTrials
Arthritis, Rheumatoid 3 D001172 ClinicalTrials
HIV Infections 3 D015658 ClinicalTrials
Friedreich Ataxia 3 D005621 ClinicalTrials
Non-alcoholic Fatty Liver Disease 3 D065626 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Fatty Liver 3 D005234 ClinicalTrials
HIV-Associated Lipodystrophy Syndrome 3 D039682 ClinicalTrials
Metabolic Syndrome 3 D024821 ClinicalTrials
Hypercholesterolemia 3 D006937 ClinicalTrials
Liver Diseases 3 D008107 ClinicalTrials
Non-alcoholic Fatty Liver Disease 3 D065626 ClinicalTrials
Renal Insufficiency, Chronic 2 D051436 ClinicalTrials
Hepatitis C, Chronic 2 D019698 ClinicalTrials
Opioid-Related Disorders 2 D009293 ClinicalTrials
Cerebral Hemorrhage 2 D002543 ClinicalTrials
Hypertension, Pulmonary 2 D006976 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Cardiovascular Diseases 2 D002318 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 2 D015464 ClinicalTrials
Infections 2 D007239 ClinicalTrials
Polycystic Ovary Syndrome 2 D011085 ClinicalTrials
Psoriasis 2 D011565 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Carcinoma, Squamous Cell 2 D002294 ClinicalTrials
Stroke 2 D020521 ClinicalTrials
Obesity 2 D009765 ClinicalTrials
Glucose Intolerance 2 D018149 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Hepatitis C 2 D006526 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Child Development Disorders, Pervasive 2 D002659 ClinicalTrials
Hepatitis 2 D006505 ClinicalTrials
Cognitive Dysfunction 2 D060825 ClinicalTrials
Polycystic Kidney Diseases 2 D007690 ClinicalTrials
Depressive Disorder, Major 2 D003865 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Liposarcoma, Myxoid 2 D018208 ClinicalTrials
Liposarcoma 2 D008080 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Amyotrophic Lateral Sclerosis 2 D000690 ClinicalTrials
Asthma 2 D001249 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Alcoholism 2 D000437 ClinicalTrials
Adrenoleukodystrophy 2 D000326 ClinicalTrials
Adrenoleukodystrophy 2 D000326 ClinicalTrials
Leukoplakia, Oral 2 D007972 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Pulmonary Alveolar Proteinosis 1 D011649 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Lupus Erythematosus, Systemic 1 D008180 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Peripheral Arterial Disease 1 D058729 ClinicalTrials
Diabetes Mellitus, Type 1 1 D003922 ClinicalTrials
Prostatic Neoplasms 1 D011471 ClinicalTrials
Inflammation 1 D007249 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 1 D020529 ClinicalTrials
Astrocytoma 1 D001254 ClinicalTrials
Gastroparesis 1 D018589 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Multiple Sclerosis 1 D009103 ClinicalTrials
Brain Neoplasms 1 D001932 ClinicalTrials
Cystic Fibrosis 1 D003550 ClinicalTrials
Meningioma 1 D008579 ClinicalTrials
Granulomatous Disease, Chronic 1 D006105 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials

Related Entries

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 111025-46-8
ChEBI 8228
ChEMBL CHEMBL595
DrugBank DB01132
DrugCentral 2179
EPA CompTox DTXSID3037129
FDA SRS X4OV71U42S
Human Metabolome Database HMDB15264
Guide to Pharmacology 2694
KEGG C07675
PharmGKB PA450970
PubChem 4829
SureChEMBL SCHEMBL4121
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