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Details

Stereochemistry RACEMIC
Molecular Formula C18H19N3O3S
Molecular Weight 357.427
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ROSIGLITAZONE

SMILES

CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C3=CC=CC=N3

InChI

InChIKey=YASAKCUCGLMORW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C18H19N3O3S
Molecular Weight 357.427
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Rosiglitazone acts as a highly selective and potent agonist at peroxisome proliferator activated receptors (PPAR) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver. It is FDA approved for the treatment of as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus. Inhibitors of CYP2C8 (e.g., gemfibrozil) may increase rosiglitazone levels; inducers of CYP2C8 (e.g., rifampin) may decrease rosiglitazone levels. Common adverse reactions include edema, weight gain, and headache.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
40.0 nM [Kd]
Conditions
PubMed

PubMed

TitleDatePubMed
Expression of phosphoenolpyruvate carboxykinase gene in human adipose tissue: induction by rosiglitazone and genetic analyses of the adipocyte-specific region of the promoter in type 2 diabetes.
2003 Dec
Reduction in the evolution of murine type II collagen-induced arthritis by treatment with rosiglitazone, a ligand of the peroxisome proliferator-activated receptor gamma.
2003 Dec
Resistin and type 2 diabetes: regulation of resistin expression by insulin and rosiglitazone and the effects of recombinant resistin on lipid and glucose metabolism in human differentiated adipocytes.
2003 Dec
Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity.
2004 Apr
Rosiglitazone prevents the impairment of human islet function induced by fatty acids: evidence for a role of PPARgamma2 in the modulation of insulin secretion.
2004 Apr
Effects of rosiglitazone and metformin on liver fat content, hepatic insulin resistance, insulin clearance, and gene expression in adipose tissue in patients with type 2 diabetes.
2004 Aug
The PPARgamma ligands PGJ2 and rosiglitazone show a differential ability to inhibit proliferation and to induce apoptosis and differentiation of human glioblastoma cell lines.
2004 Aug
Decreased expression of peroxisome proliferator activated receptor gamma in cftr-/- mice.
2004 Aug
[Anti-hypertensive effect of rosiglitazone in non-diabetic essential hypertension].
2004 Dec
Effect of peroxisome proliferator-activated receptor gamma agonist, rosiglitazone, on dedifferentiated thyroid cancers.
2004 Dec
Peroxisome proliferator-activated receptor gamma ligands suppress liver carcinogenesis induced by diethylnitrosamine in rats.
2004 Dec 1
A yeast two-hybrid technology-based system for the discovery of PPARgamma agonist and antagonist.
2004 Dec 15
Rosiglitazone, a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation.
2004 Jan 1
Reduction of intracellular cholesterol accumulation in THP-1 macrophages by a combination of rosiglitazone and atorvastatin.
2004 Jul 1
Evidence for a potent antiinflammatory effect of rosiglitazone.
2004 Jun
Rosiglitazone induction of Insig-1 in white adipose tissue reveals a novel interplay of peroxisome proliferator-activated receptor gamma and sterol regulatory element-binding protein in the regulation of adipogenesis.
2004 Jun 4
PPAR(gamma) agonist rosiglitazone improves vascular function and lowers blood pressure in hypertensive transgenic mice.
2004 Mar
Rosiglitazone facilitates angiogenic progenitor cell differentiation toward endothelial lineage: a new paradigm in glitazone pleiotropy.
2004 Mar 23
Rosiglitazone improves insulin sensitivity, glucose tolerance and ambulatory blood pressure in subjects with impaired glucose tolerance.
2004 May
Transactivation of the PPAR-responsive enhancer module in chemopreventive glutathione S-transferase gene by the peroxisome proliferator-activated receptor-gamma and retinoid X receptor heterodimer.
2004 May 15
Mitochondrial remodeling in adipose tissue associated with obesity and treatment with rosiglitazone.
2004 Nov
Hepatic lipase mRNA, protein, and plasma enzyme activity is increased in the insulin-resistant, fructose-fed Syrian golden hamster and is partially normalized by the insulin sensitizer rosiglitazone.
2004 Nov
Rosiglitazone upregulates caveolin-1 expression in THP-1 cells through a PPAR-dependent mechanism.
2004 Nov
Chronic heart failure-related interventions after starting rosiglitazone in patients receiving insulin.
2004 Oct
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
Comparison of the effects of pioglitazone and rosiglitazone on macrophage foam cell formation.
2004 Oct 22
Rosiglitazone treatment improves insulin regulation and dyslipidemia in type 2 diabetic cynomolgus monkeys.
2004 Sep
Altered adipokine response in murine 3T3-F442A adipocytes treated with protease inhibitors and nucleoside reverse transcriptase inhibitors.
2005
The antidiabetic agent rosiglitazone upregulates SERCA2 and enhances TNF-alpha- and LPS-induced NF-kappaB-dependent transcription and TNF-alpha-induced IL-6 secretion in ventricular myocytes.
2005
Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.
2005 Aug
Rosiglitazone, PPAR-gamma receptor ligand, decreases the viability of rat prolactin-secreting pituitary tumor cells in vitro.
2005 Feb
Effect of rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 on bleomycin-induced lung injury.
2005 Feb
Chaperone proteins involved in troglitazone-induced toxicity in human hepatoma cell lines.
2005 Feb
The effects of rosiglitazone on fatty acid and triglyceride metabolism in type 2 diabetes.
2005 Jan
Rosiglitazone up-regulates lipoprotein lipase, hormone-sensitive lipase and uncoupling protein-1, and down-regulates insulin-induced fatty acid synthase gene expression in brown adipocytes of Wistar rats.
2005 Jun
Enhanced insulin-stimulated glycogen synthesis in response to insulin, metformin or rosiglitazone is associated with increased mRNA expression of GLUT4 and peroxisomal proliferator activator receptor gamma co-activator 1.
2005 Jun
Rosiglitazone induces interleukin-1 receptor antagonist in interleukin-1beta-stimulated rat synovial fibroblasts via a peroxisome proliferator-activated receptor beta/delta-dependent mechanism.
2005 Mar
The peroxisome proliferator-activated receptor gamma ligand rosiglitazone delays the onset of inflammatory bowel disease in mice with interleukin 10 deficiency.
2005 Mar
Thiazolidinediones inhibit proliferation of microvascular and macrovascular cells by a PPARgamma-independent mechanism.
2005 Mar
Development of a complex scintillation proximity assay for high-throughput screening of PPARgamma modulators.
2005 Mar
Comparison of pioglitazone with other antidiabetic drugs for associated incidence of liver failure: no evidence of increased risk of liver failure with pioglitazone.
2005 Mar
Rosiglitazone causes bone loss in mice by suppressing osteoblast differentiation and bone formation.
2005 Mar
The influence of adiponectin gene polymorphism on the rosiglitazone response in patients with type 2 diabetes.
2005 May
Effects of metformin and rosiglitazone treatment on insulin signaling and glucose uptake in patients with newly diagnosed type 2 diabetes: a randomized controlled study.
2005 May
Rosiglitazone increases indexes of stearoyl-CoA desaturase activity in humans: link to insulin sensitization and the role of dominant-negative mutation in peroxisome proliferator-activated receptor-gamma.
2005 May
Mechanism of the anti-inflammatory effect of thiazolidinediones: relationship with the glucocorticoid pathway.
2005 May
Selective activation of PPARgamma in breast, colon, and lung cancer cell lines.
2005 May 12
Fatty acids and expression of adipokines.
2005 May 30
Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions.
2005 Oct
Peroxisome proliferator-activated receptor-gamma ligands suppress fibronectin gene expression in human lung carcinoma cells: involvement of both CRE and Sp1.
2005 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Start at 4 mg daily in single or divided doses; do not exceed 8 mg daily.
Route of Administration: Oral
In Vitro Use Guide
Rosiglitazone treatment (5 uM) prevents NO and prostacyclin overproduction by inhibiting microparticles-induced iNOS and COX-2 expression.
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:08:26 UTC 2019
Edited
by admin
on Tue Oct 22 00:08:26 UTC 2019
Record UNII
05V02F2KDG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ROSIGLITAZONE
EMA EPAR   HSDB   INN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
ROSIGLIZOLE
Brand Name English
BRL-49653
Code English
ROSIGLITAZONE [WHO-DD]
Common Name English
ROSIGLITAZONE [MI]
Common Name English
ROSIGLITAZONE [INN]
Common Name English
ROSIGLITAZONE [EMA EPAR]
Common Name English
REZULT
Brand Name English
TDZ-01
Code English
ROSIGLITAZONE [VANDF]
Common Name English
2,4-THIAZOLIDINEDIONE, 5-((4-(2-(METHYL-2-PYRIDINYLAMINO)ETHOXY)PHENYL)METHYL)-
Systematic Name English
ROSIGLITAZONE [MART.]
Common Name English
ROSIGLITAZONE [IARC]
Common Name English
ROSVEL
Brand Name English
GAUDIL
Brand Name English
5-((4-(2-(METHYL-2-PYRIDINYLAMINO)ETHOXY)PHENYL)METHYL)-2,4-THIAZOLIDINEDIONE
Systematic Name English
ROSIGLITAZONE [HSDB]
Common Name English
5-(4-(2-(N-METHYL-N-(2-PYRIDINYL)AMINO)ETHOXY)BENZYL)-2,4-THIAZOLIDINEDIONE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C98241
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000011272
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
WHO-ATC A10BD03
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
LIVERTOX 863
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000180190
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
WHO-ATC A10BD04
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
WHO-VATC QA10BG02
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000175374
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NCI_THESAURUS C1934
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
WHO-VATC QA10BD04
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
WHO-ATC A10BG02
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000170119
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000011272
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
WHO-VATC QA10BD03
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000180186
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000170119
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
NDF-RT N0000011272
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
Code System Code Type Description
EVMPD
SUB10388MIG
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
INN
7662
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
PUBCHEM
77999
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
HSDB
122320-73-4
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
DRUG BANK
DB00412
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
WIKIPEDIA
ROSIGLITAZONE
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
IUPHAR
1056
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
MESH
C089730
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
NCI_THESAURUS
C62076
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
EPA CompTox
122320-73-4
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
MERCK INDEX
M9666
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY Merck Index
CAS
122320-73-4
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
ChEMBL
CHEMBL121
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
LactMed
122320-73-4
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY
RXCUI
84108
Created by admin on Tue Oct 22 00:08:26 UTC 2019 , Edited by admin on Tue Oct 22 00:08:26 UTC 2019
PRIMARY RxNorm
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