Drug Details

General Information of the Drug (ID: DR8032)
Name
Rosiglitazone
Synonyms
Avandia; 5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)benzyl)thiazolidine-2,4-dione; Brl-49653; Rosiglizole; Brl 49653; rosiglitazone (Avandia); BRL49653; Avandaryl; TDZ 01; Avandamet; C18H19N3O3S; CHEBI:50122; MFCD00871760; Rosigilitazone; 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioate; 2,4-Thiazolidinedione, 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-; 2,4-thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]-; NCGC00095124-01; BRL 49653C; 5-[4-[2-[Methyl(2-pyridyl)amino]ethoxy]benzyl]thiazolidine-2,4-dione; 5-(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzyl)-1,3-thiazolidine-2,4-dione; DSSTox_CID_17131; DSSTox_RID_79303; DSSTox_GSID_37131; Rosiglitazone [INN:BAN]; 5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione; CAS-122320-73-4; SR-01000763023; rosiglitazona; rosiglitazonum; Rezult; Rosi; HSDB 7555; Rosiglitazone base; 5-((4-(2-(methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione; 5-[4-[2-[N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione; Gaudil (TN); Rosiglitazone (INN); 1132641-22-5; Spectrum_001703; 1217260-35-9; Spectrum2_001241; Spectrum3_000997; Spectrum4_001125; Spectrum5_001464; SCHEMBL5169; Dioxopromethazinehydrochloride; BSPBio_002693; KBioGR_001609; KBioSS_002183; SPECTRUM1504263; SPBio_001142; GTPL1056; TDZ-01; DTXSID7037131; SCHEMBL14383595; KBio2_002183; KBio2_004751; KBio2_007319; KBio3_001913; Rosiglitazone, >=98% (HPLC); HMS1922J11; HMS2094O13; HMS3649G08; HMS3656K16; HMS3744M11; HMS3871L03; HMS3884N08; Pharmakon1600-01504263; ACT04332; BCP03047; Tox21_111434; ANW-44906; BBL029079; BDBM50030474; CCG-39102; NSC758698; STL350047; AKOS015894872; Tox21_111434_1; AC-3459; BCP9000017; CS-1088; DB00412; MCULE-8293284864; MP-0331; NSC-758698; SB17326; VA11695; 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]-phenyl]methyl]-2,4-thiazolidine-dione; NCGC00095124-02; NCGC00095124-03; NCGC00095124-04; NCGC00095124-05; NCGC00095124-06; NCGC00095124-08; AK-72839; HY-17386; SY031184; BCP0726000232; AB0011992; FT-0602578; R0106; S2556; SW197573-6; 20R734; 6P-065; D08491; J10213; S00306; AB00698473-15; AB00698473-17; AB00698473-18; AB00698473-19; AB00698473_20; AB00698473_21; AB00698473_22; AB00698473_23; Q424771; Q-201681; SR-01000763023-5; SR-01000763023-6; BRD-A97437073-001-02-3; BRD-A97437073-001-03-1; BRD-A97437073-001-04-9; SR-01000763023-12; (RS)-5-{4-[2-(Methyl-2-pyridylamino)ethoxy]benzyl}-2,4-thiazolidinedion; 5-(4-(2-(Methyl(pyridin-2-yl)amino)ethoxy)-benzyl)thiazolidine-2,4-dione; 5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4dione; IDMB (1uM BRL49653, 1uM Dexamethasone, 0.5uM IBMX, 10ug/mL Insulin); (+/-)-5-[p-[2-(methyl-2-pyridylamino)ethoxy]benzyl]-2,4-thiazolidinedione; 2,4-Thiazolidinedione, 5-[[4-[2-(methyl-2-pyridinylamino)ethoxy]phenyl]methyl]- (9CI); 5-[[4-[2-(methyl-(2-pyridyl)amino)ethoxy]phenyl]methyl] thiazolidine-2,4-dione; 5-[[4-[2-(methyl-2-pyridinylamino) ethoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-[[4-[2-(Methyl-2-pyridinylamino)e thoxy]phenyl]methyl]-2,4-thiazolidinedione; 5-[[4-[2-(methyl-pyridin-2-ylamino)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione; 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl] thiazolidine-2,4-dione; 5-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]phenyl methyl]thiazolidine-2,4-dione
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Molecular Type
Small molecule
Disease Prostate cancer [ICD-11: 2C82] Phase 3 [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
99% of drug becomes completely available to its intended biological destination(s)
Clearance
The apparent oral clearance of drug is 3.03 +/- 0.87 L/h
Clearance
The drug present in the plasma can be removed from the body at the rate of 0.65 mL/min/kg
Elimination
0% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 3 - 4 hours
Half-life
The concentration or amount of drug in body reduced by one-half in 3.9 hours
Metabolism
The drug is metabolized via the hepatic
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.3721 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.002%
Vd
The volume of distribution (Vd) of drug is 17.6 L
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.2 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 0.04 mg/mL
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Formula
C18H19N3O3S
PubChem CID
77999
Canonical SMILES
CN(CCOC1=CC=C(C=C1)CC2C(=O)NC(=O)S2)C3=CC=CC=N3
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)
InChIKey
YASAKCUCGLMORW-UHFFFAOYSA-N
CAS Number
CAS 122320-73-4
DrugBank ID
DB00412
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Honokiol      Magnolia officinalis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Down-regulation Expression CCNE1  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Down-regulation Expression RB1  Molecule Info 
Pathway MAP
                    In-vitro Model Mahlavu CVCL_0405 Hepatocellular carcinoma Homo sapiens
SK-HEP-1 CVCL_0525 Hepatocellular carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Honokiol combined with rosiglitazone showed more effective growth inhibition in hepatoma cells mediated through the regulation of G0/G1 phase-related proteins p21, cyclin D1, cyclin E1, and Rb and cell cycle progression.
          Semaglutide      Heloderma suspectum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
Down-regulation Expression IL1B  Molecule Info 
Pathway MAP
Down-regulation Expression IL6  Molecule Info 
Pathway MAP
Down-regulation Expression mTOR  Molecule Info 
Pathway MAP
Down-regulation Expression PIK3CB  Molecule Info 
Pathway MAP
Down-regulation Expression TNF  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Increase ROS accumulation
                    In-vivo Model Fifty healthy male Sprague-Dawley (SD) rats with eight-week-old and body weight of 200.0 +/- 18.4 g were used in this study.
                    Experimental
                    Result(s)		 Combined semaglutide with RSG exhibited synergistically protective efficacies on retinal cells by decreasing the GFAP expression, inhibiting oxidative stress and PI3K/Akt/MTOR signaling-transduction in DR model rats.
References
Reference 1 ClinicalTrials.gov (NCT00182052) Rosiglitazone (Avandia) vs. Placebo for Androgen Dependent Prostate Cancer
Reference 2 Combined effect of honokiol and rosiglitazone on cell growth inhibition through enhanced G0/G1 phase arrest in hepatoma cells. J Chin Med Assoc. 2016 Aug;79(8):415-21.
Reference 3 Combination therapy with semaglutide and rosiglitazone as a synergistic treatment for diabetic retinopathy in rodent animals. Life Sci. 2021 Mar 15;269:119013.
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