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Details

Stereochemistry EPIMERIC
Molecular Formula C18H19N3O3S.C4H6O6
Molecular Weight 507.514
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Rosiglitazone tartrate

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C3=NC=CC=C3

InChI

InChIKey=ADQQXOGMNHWLRB-LREBCSMRSA-N
InChI=1S/C18H19N3O3S.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1

HIDE SMILES / InChI
Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C18H19N3O3S
Molecular Weight 357.427
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/mtm/rosiglitazone.html http://www.rxlist.com/avandia-drug.htm http://www.wikidoc.org/index.php/Rosiglitazone

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

1999
175
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 40.0 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
AVANDIA

Approved Use

After consultation with a healthcare professional who has considered and advised the patient of the risks and benefits of rosiglitazone, AVANDAMET® is indicated as an adjunct to diet and exercise to improve glycemic control when treatment with both rosiglitazone and metformin is appropriate in adults with type 2 diabetes mellitus who either are: already taking rosiglitazone, or not already taking rosiglitazone and unable to achieve glycemic control on other diabetes medications and, in consultation with their healthcare provider, have decided not to take pioglitazone (ACTOS®) or pioglitazone-containing products (ACTOPLUS MET®, ACTOPLUS MET XR®, DUETACT®) for medical reasons. Other Important Limitations of Use: Due to its mechanism of action, rosiglitazone is active only in the presence of endogenous insulin. Therefore, AVANDAMET should not be used in patients with type 1 diabetes. Coadministration of AVANDAMET with insulin is not recommended [see Warnings and Precautions (5.2, 5.3)

Launch Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
598 ng/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
432 ng/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2971 ng × h/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
2890 ng × h/mL
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.37 h
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FASTED
3.59 h
DRUG LABEL
https://www.fda.gov/media/75754/download
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ROSIGLITAZONE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: FED
Doses

Doses

DosePopulationAdverse events​
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
unhealthy, 53.1
Health Status: unhealthy
Age Group: 53.1
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
DLT: Headache, Malaise...
Disc. AE: Pain in leg...
Dose limiting toxicities:
Headache (3.1%)
Malaise (3.1%)
Oedema legs (9.4%)
AEs leading to
discontinuation/dose reduction:
Pain in leg (3.1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
unhealthy, 60
Health Status: unhealthy
Age Group: 60
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
Disc. AE: Macular edema...
AEs leading to
discontinuation/dose reduction:
Macular edema
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Disc. AE: Congestive heart failure, Myocardial ischemia...
AEs leading to
discontinuation/dose reduction:
Congestive heart failure
Myocardial ischemia (2%)
Fluid retention
Edema
Weight gain
Anemia
Macular edema
Fracture bone
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Headache 3.1%
DLT
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
unhealthy, 53.1
Health Status: unhealthy
Age Group: 53.1
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Malaise 3.1%
DLT
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
unhealthy, 53.1
Health Status: unhealthy
Age Group: 53.1
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Pain in leg 3.1%
Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
unhealthy, 53.1
Health Status: unhealthy
Age Group: 53.1
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Oedema legs 9.4%
DLT
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
unhealthy, 53.1
Health Status: unhealthy
Age Group: 53.1
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/18503774
Macular edema Disc. AE
20 mg single, oral
Overdose
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
unhealthy, 60
Health Status: unhealthy
Age Group: 60
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/25390127
Myocardial ischemia 2%
Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Anemia Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Congestive heart failure Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Edema Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Fluid retention Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Fracture bone Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Macular edema Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
Weight gain Disc. AE
8 mg 1 times / day multiple, oral
Recommended
Dose: 8 mg, 1 times / day
Route: oral
Route: multiple
Dose: 8 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
unhealthy
Health Status: unhealthy
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021071s031lbl.pdf
PubMed

PubMed

TitleDatePubMed
Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions.
2005-10
Peroxisome proliferator-activated receptor-gamma ligands suppress fibronectin gene expression in human lung carcinoma cells: involvement of both CRE and Sp1.
2005-09
Automated screening with confirmation of mechanism-based inactivation of CYP3A4, CYP2C9, CYP2C19, CYP2D6, and CYP1A2 in pooled human liver microsomes.
2005-08
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.
2005-06
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.
2005-06
Fatty acids and expression of adipokines.
2005-05-30
Selective activation of PPARgamma in breast, colon, and lung cancer cell lines.
2005-05-12
The influence of adiponectin gene polymorphism on the rosiglitazone response in patients with type 2 diabetes.
2005-05
Effects of metformin and rosiglitazone treatment on insulin signaling and glucose uptake in patients with newly diagnosed type 2 diabetes: a randomized controlled study.
2005-05
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.
2005-05
Mechanism of the anti-inflammatory effect of thiazolidinediones: relationship with the glucocorticoid pathway.
2005-05
Rosiglitazone induces interleukin-1 receptor antagonist in interleukin-1beta-stimulated rat synovial fibroblasts via a peroxisome proliferator-activated receptor beta/delta-dependent mechanism.
2005-03
The peroxisome proliferator-activated receptor gamma ligand rosiglitazone delays the onset of inflammatory bowel disease in mice with interleukin 10 deficiency.
2005-03
Thiazolidinediones inhibit proliferation of microvascular and macrovascular cells by a PPARgamma-independent mechanism.
2005-03
Development of a complex scintillation proximity assay for high-throughput screening of PPARgamma modulators.
2005-03
Comparison of pioglitazone with other antidiabetic drugs for associated incidence of liver failure: no evidence of increased risk of liver failure with pioglitazone.
2005-03
Rosiglitazone causes bone loss in mice by suppressing osteoblast differentiation and bone formation.
2005-03
Rosiglitazone, PPAR-gamma receptor ligand, decreases the viability of rat prolactin-secreting pituitary tumor cells in vitro.
2005-02
Effect of rosiglitazone and 15-deoxy-Delta12,14-prostaglandin J2 on bleomycin-induced lung injury.
2005-02
Chaperone proteins involved in troglitazone-induced toxicity in human hepatoma cell lines.
2005-02
The effects of rosiglitazone on fatty acid and triglyceride metabolism in type 2 diabetes.
2005-01
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
A yeast two-hybrid technology-based system for the discovery of PPARgamma agonist and antagonist.
2004-12-15
Peroxisome proliferator-activated receptor gamma ligands suppress liver carcinogenesis induced by diethylnitrosamine in rats.
2004-12-01
[Anti-hypertensive effect of rosiglitazone in non-diabetic essential hypertension].
2004-12
Effect of peroxisome proliferator-activated receptor gamma agonist, rosiglitazone, on dedifferentiated thyroid cancers.
2004-12
Mitochondrial remodeling in adipose tissue associated with obesity and treatment with rosiglitazone.
2004-11
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.
2004-11
Rosiglitazone upregulates caveolin-1 expression in THP-1 cells through a PPAR-dependent mechanism.
2004-11
Comparison of the effects of pioglitazone and rosiglitazone on macrophage foam cell formation.
2004-10-22
Chronic heart failure-related interventions after starting rosiglitazone in patients receiving insulin.
2004-10
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004-10
Rosiglitazone treatment improves insulin regulation and dyslipidemia in type 2 diabetic cynomolgus monkeys.
2004-09
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.
2004-08
The PPARgamma ligands PGJ2 and rosiglitazone show a differential ability to inhibit proliferation and to induce apoptosis and differentiation of human glioblastoma cell lines.
2004-08
Decreased expression of peroxisome proliferator activated receptor gamma in cftr-/- mice.
2004-08
Reduction of intracellular cholesterol accumulation in THP-1 macrophages by a combination of rosiglitazone and atorvastatin.
2004-07-01
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.
2004-06-04
Evidence for a potent antiinflammatory effect of rosiglitazone.
2004-06
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.
2004-05-15
Rosiglitazone improves insulin sensitivity, glucose tolerance and ambulatory blood pressure in subjects with impaired glucose tolerance.
2004-05
Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity.
2004-04
Rosiglitazone prevents the impairment of human islet function induced by fatty acids: evidence for a role of PPARgamma2 in the modulation of insulin secretion.
2004-04
Rosiglitazone facilitates angiogenic progenitor cell differentiation toward endothelial lineage: a new paradigm in glitazone pleiotropy.
2004-03-23
PPAR(gamma) agonist rosiglitazone improves vascular function and lowers blood pressure in hypertensive transgenic mice.
2004-03
Rosiglitazone, a ligand of the peroxisome proliferator-activated receptor-gamma, reduces acute inflammation.
2004-01-01
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.
2003-12
Reduction in the evolution of murine type II collagen-induced arthritis by treatment with rosiglitazone, a ligand of the peroxisome proliferator-activated receptor gamma.
2003-12
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.
2003-12
Patents

Patents

06515132
8
JP2002543077A
8
JP2004536047A
26
JP2008195625A
8
JP2011252007A
8
JP4365554B2
24
JP4741458B2
8

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 Wed Apr 02 15:35:07 GMT 2025
Edited
by admin
on Wed Apr 02 15:35:07 GMT 2025
Record UNII
3DQ9JH6CDA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Rosiglitazone tartrate [WHO-DD]
Preferred Name English
Rosiglitazone tartrate
Common Name English
2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-, (2R,3R)-2,3-dihydroxybutanedioate (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
3DQ9JH6CDA
Created by admin on Wed Apr 02 15:35:07 GMT 2025 , Edited by admin on Wed Apr 02 15:35:07 GMT 2025
PRIMARY
PUBCHEM
9849118
Created by admin on Wed Apr 02 15:35:07 GMT 2025 , Edited by admin on Wed Apr 02 15:35:07 GMT 2025
PRIMARY
CAS
397263-86-4
Created by admin on Wed Apr 02 15:35:07 GMT 2025 , Edited by admin on Wed Apr 02 15:35:07 GMT 2025
PRIMARY
SMS_ID
300000047319
Created by admin on Wed Apr 02 15:35:07 GMT 2025 , Edited by admin on Wed Apr 02 15:35:07 GMT 2025
PRIMARY
Related Record Type Details
Structure of Tartaric Acid
PARENT -> SALT/SOLVATE
Structure of ROSIGLITAZONE
PARENT -> SALT/SOLVATE
NIH
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