TROGLITAZONE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC A10BG01
UNII I66ZZ0ZN0E
EPA CompTox DTXSID8023719

Structure

InChI Key GXPHKUHSUJUWKP-UHFFFAOYSA-N
Smiles Cc1c(C)c2c(c(C)c1O)CCC(C)(COc1ccc(CC3SC(=O)NC3=O)cc1)O2
InChI
InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H27NO5S
Molecular Weight 441.55
AlogP 4.37
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 5.0
Polar Surface Area 84.86
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 31.0

Bioactivity

Mechanism of Action Action Reference
Peroxisome proliferator-activated receptor gamma agonist AGONIST PubMed Wikipedia
Protein: Peroxisome proliferator-activated receptor gamma
Description: Peroxisome proliferator-activated receptor gamma
Organism : Homo sapiens
P37231 ENSG00000132170
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- - - - 84
Enzyme Oxidoreductase
- 20000 - 10500 -
Enzyme Phosphatase Protein Phosphatase Tyrosine protein phosphatase
- 55000 - - 29
Enzyme Transferase
- - - 20000 -
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 800 - - -
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
- - - - 23
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
215-2600 300-2600 - 302-3800 96
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
6900-31600 - - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 48
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 2700-6900 - - -
Transporter Primary active transporter ATP-binding cassette ABCC subfamily
- 31000 - - -
Unclassified protein
- - - 52 -
Assay Description Organism Bioactivity Reference
Effective concentration for 50% enhancement of insulin-induced triglyceride accumulation in 3T3-L1 cells Mus musculus 130.0 nM Effective concentration for 50% enhancement of insulin-induced triglyceride accumulation in 3T3-L1 cells Mus musculus 130.0 nM
Agonist activity for Human PPAR gamma receptor in transcriptional activation assay Homo sapiens 550.0 nM
The compound was tested in vivo(ob/ob mouse) for intestinal absorption against insulin, at a concentration of 200 mg/kg/day. Mus musculus 15.0 %
The compound was tested in vivo(ob/ob mouse) for intestinal absorption against plasma glucose at a concentration of 200 mg/kg/day. Mus musculus 34.0 %
Agonist activity for murine PPAR gamma receptor in transcriptional activation assay Mus musculus 780.0 nM
Activation of peroxisome proliferator activated receptor gamma measured by induction of 50% of maximum alkaline phosphatase activity, transfection assay in CV-1 cells None 537.03 nM
Inhibition of PTPase activity in rat hepatic membrane at a concentration of 250 uM using pNPP as the substrate None 29.0 %
Transcriptional activation of peroxisome proliferator activated receptor gamma Homo sapiens 537.03 nM
Binding affinity against Peroxisome proliferator activated receptor gamma (PPAR gamma) None 302.0 nM
In vitro binding to peroxisome proliferator activated receptor gamma (PPAR gamma) using [3H]-BRL 49653 as radioligand in scintillation proximity assay (SPA) None 302.0 nM
In vitro inhibitory activity against rat microsomal lipid peroxidation (m-LPO) Rattus norvegicus 0.1 ug.mL-1
In vitro transactivation using receptor transactivation assay against hPPAR gamma None 980.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 48.2 %
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: [3H] Lysergic acid diethylamide) None 835.0 nM
DRUGMATRIX: Carbonic Anhydrase II enzyme inhibition (substrate: 4-Nitrophenyl acetate (4-NPA)) Homo sapiens 970.0 nM
Agonist activity at human PPARgamma expressed in CHO cells co-transfected with pGL3-PPRE3-TK-luc assessed as transactivation after 24 hrs by firefly luciferase reporter gene assay Homo sapiens 440.0 nM
Transactivation of GAL4-fused PPARgamma LBD expressed in HepG2 cells after 20 hrs by luminescence assay None 730.0 nM
Transactivation of human PPARgamma expressed in african green monkey CV1 cells by luciferase reporter gene assay Homo sapiens 400.0 nM
Binding affinity to GST-tagged human PPARgamma by TR-FRET analysis Homo sapiens 300.0 nM
Agonist activity at human recombinant PPARgamma expressed in CHO cells cotransfected with pGL3-PPRE3-TK-luc reporter assessed as beta-galactosidase activity at after 24 hrs by luciferase based transactivation assay Homo sapiens 440.0 nM
TP_TRANSPORTER: inhibition of estrone-3-sulfate uptake (Estrone-3-sulfate: 9.2 nM) by Troglitazone at a concentration of 10uM in OATP-C-expressing Xenopus oocytes Xenopus laevis 35.0 %
Activation of PPARgamma transfected in HEK293 cells after 18 hrs by firefly luciferase reporter gene-based luminescence assay relative to control Homo sapiens 400.0 nM
Transactivation of GAL4-fused PPARgamma ligand binding domain transfected in human HepG2 cells after 20 hrs by luciferase reporter gene assay Homo sapiens 720.0 nM
Inhibition of mouse Tdo2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 100 uM after 45 mins by spectrophotometric analysis relative to control Mus musculus 20.0 %
Inhibition of mouse Ido2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 20 uM after 45 mins by spectrophotometric analysis relative to control Mus musculus 55.0 %
Agonist activity at PPARgamma (unknown origin) Homo sapiens 340.0 nM
Inhibition of Cav1.2 calcium current measured using whole cell patch clamp in guinea pig ventricular myocytes Cavia porcellus 800.0 nM
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 53.2 nM
Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARgamma LBD at 10 uM by TR-FRET assay relative to control Homo sapiens 96.2 %
Displacement of Fluormone-Pan-PPAR Green from human GST-tagged PPARdelta LBD at 10 uM by TR-FRET assay relative to control Homo sapiens 23.4 %
Displacement of fluormone Pan-PPAR Green from human GST-tagged PPARgamma-LBD by TR-FRET assay Homo sapiens 380.0 nM
Competitive displacement of fluorescently labelled PPAR tracer ligand from GST-tagged human PPARgamma ligand binding domain after 1 hr in dark by TR-FRET competitive binding assay Homo sapiens 370.0 nM
Inhibition of recombinant human CYP2C19 expressed in insect cell microsomes at 10 uM using Luciferin-H EGE as substrate preincubated for 20 mins followed by NADPH addition measured after 30 mins by luminometric method Homo sapiens 84.0 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens 34.92 %
Agonist activity at PPARgamma (unknown origin) incubated for 3 to 16 hrs by pathhunter nuclear hormone receptor assay Homo sapiens 215.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 18.06 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.08 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.08 %
Binding affinity to human recombinant PPARgamma by Cheng-Prusoff equation based competitive binding TR-FRET assay Homo sapiens 400.0 nM
Induction of adipogenesis in human AT-MSC assessed as adiponectin secretion in IDX medium incubated for 5 days by ELISA Homo sapiens 860.0 nM
Downregulation of FOXM1 expression in human MDA-MB-231 cells at 40 uM after 48 hrs by Western blot analysis relative to control Homo sapiens 80.0 %
Binding affinity to recombinant FOXM1 DBD (unknown origin) expressed in Escherichia coli BL21 (DE3) assessed as disruption of FOXM1-DNA complex preincubated for 1.5 hrs followed by DNA addition measured after 20 mins by EMSA Homo sapiens 51.97 nM

Cross References

Resources Reference
ChEBI 9753
ChEMBL CHEMBL408
DrugBank DB00197
DrugCentral 2767
FDA SRS I66ZZ0ZN0E
Guide to Pharmacology 2693
KEGG D00395
PDB TDZ
PharmGKB PA451799
PubChem 5591
SureChEMBL SCHEMBL4959
ZINC ZINC00968279
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