ROSIGLITAZONE MALEATE

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Search structure


Trade Names	AVANDIA ROSIGLITAZONE ROSIGLITAZONE MALEATE
Synonyms	Avandia BRL-49653 BRL-49653-C BRL-49653C NSC-717764 Rosiglitazone maleate Rosiglitzazone maleate
Status
Molecule Category	Mixture
UNII	KX2339DP44
EPA CompTox	DTXSID2023569


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	SUFUKZSWUHZXAV-BTJKTKAUSA-N
Smiles	CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1.O=C(O)/C=C\C(=O)O
InChI	InChI=1S/C18H19N3O3S.C4H4O4/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;5-3(6)1-2-4(7)8/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1-

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C22H23N3O7S
Molecular Weight	473.51
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

Bioactivity

Mechanism of Action	Action	Reference
Peroxisome proliferator-activated receptor gamma agonist	AGONIST	DailyMed


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(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 3	-	-	-	10000	-
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	730	-	-	14-136	-
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 1	-	-	15010	-	-

Assay Description	Organism	Bioactivity	Reference
Peroxisome proliferator activated receptor gamma agonistic activity in HepG2 cells.	None	730.0 nM
Binding affinity towards human peroxisome proliferator activated receptor gamma (PPAR gamma) was determined by HTRF assay	None	14.0 nM
Binding affinity towards peroxisome proliferator activated receptor gamma (PPAR gamma)	None	136.0 nM
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	5.02 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	0.27 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	9.63 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	11.6 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	18.39 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	0.75 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-9.6 %
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	10.32 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.563 %
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	-0.18 %		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	-0.18 %

Cross References

Resources	Reference
ChEBI	8892
ChEMBL	CHEMBL843
FDA SRS	KX2339DP44
PubChem	5281055
SureChEMBL	SCHEMBL19023

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).