ROSIGLITAZONE

Search structure
Synonyms:
Status: Approved (1999) Withdrawn (2010)
Entry Type: Small molecule
Molecule Category: Parent
ATC: A10BG02
UNII: 05V02F2KDG

Structure
InChI Key YASAKCUCGLMORW-UHFFFAOYSA-N
Smile CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1
InChI
InChI=1S/C18H19N3O3S/c1-21(16-4-2-3-9-19-16)10-11-24-14-7-5-13(6-8-14)12-15-17(22)20-18(23)25-15/h2-9,15H,10-12H2,1H3,(H,20,22,23)

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H19N3O3S
Molecular Weight 357.44
AlogP 2.49
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 71.53
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 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- - - - 56
Enzyme Ligase
- - - - 9
Enzyme Oxidoreductase
- 832 - 27600 -
Enzyme Phosphatase Protein Phosphatase Tyrosine protein phosphatase
- - - - 25-25
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M4 family
- - - - 7
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 29500 - - 9-58
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Angiotensin receptor
- - - 0 -
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
11482 - - - -
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
4-10580 80 - - 3-45
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
1600 - - - 0
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
2-43710 8-22000 1-4980 6-440 46-77
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC10 family of sodium-bile acid co-transporters
- 5100 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 10
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 2800-6400 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 21000 - - -
Unclassified protein
- 1100 - 31 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Alzheimer Disease 3 D000544 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Diabetes Mellitus, Type 2 3 D003924 ClinicalTrials
Prostatic Neoplasms 3 D011471 ClinicalTrials
Diabetic Neuropathies 3 D003929 ClinicalTrials
Lipid Metabolism Disorders 3 D052439 ClinicalTrials
Metabolic Syndrome 3 D024821 ClinicalTrials
Multiple Organ Failure 3 D009102 ClinicalTrials
Hypertension 3 D006973 ClinicalTrials
Metabolic Diseases 3 D008659 ClinicalTrials
Glucose Intolerance 3 D018149 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Glucose Intolerance 3 D018149 ClinicalTrials
Hypercholesterolemia 3 D006937 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
Prediabetic State 2 D011236 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Insulin Resistance 2 D007333 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Sezary Syndrome 2 D012751 ClinicalTrials
Asthma 2 D001249 ClinicalTrials
Endometriosis 2 D004715 ClinicalTrials
Cognitive Dysfunction 2 D060825 ClinicalTrials
Mycosis Fungoides 2 D009182 ClinicalTrials
Erectile Dysfunction 1 D007172 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Malaria 1 D008288 ClinicalTrials
Anemia 1 D000740 ClinicalTrials
Nausea 1 D009325 ClinicalTrials
Glomerulosclerosis, Focal Segmental 1 D005923 ClinicalTrials
Breast Neoplasms 1 D001943 ClinicalTrials
Malaria, Falciparum 1 D016778 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials

Related Entries

MCS

Scaffolds

Cross References

Resources Reference
CAS NUMBER 122320-73-4
ChEBI 50122
ChEMBL CHEMBL121
DrugBank DB00412
DrugCentral 2405
EPA CompTox DTXSID7037131
FDA SRS 05V02F2KDG
Human Metabolome Database HMDB0005031
Guide to Pharmacology 1056
PharmGKB PA451283
PubChem 77999
SureChEMBL SCHEMBL5169
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