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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
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

Primary TargetPharmacologyConditionPotency
40.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AVANDIA

Cmax

ValueDoseCo-administeredAnalytePopulation
432 ng/mL
8 mg single, oral
ROSIGLITAZONE plasma
Homo sapiens
598 ng/mL
8 mg single, oral
ROSIGLITAZONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2890 ng × h/mL
8 mg single, oral
ROSIGLITAZONE plasma
Homo sapiens
2971 ng × h/mL
8 mg single, oral
ROSIGLITAZONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.59 h
8 mg single, oral
ROSIGLITAZONE plasma
Homo sapiens
3.37 h
8 mg single, oral
ROSIGLITAZONE plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
05V02F2KDG
Record Status Validated (UNII)
Record Version