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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-17 09:52:37 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005031
Secondary Accession Numbers
  • HMDB05031
Metabolite Identification
Common NameRosiglitazone
DescriptionRosiglitazone is an anti-diabetic drug from the thiazolidinedione class. Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha-binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFκB) levels fall and inhibitor (IκB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes; Rosiglitazone is an anti-diabetic drug from the thiazolidinedione class. It is being marketed as Avandia by the pharmaceutical company GlaxoSmithKline, both as a standalone preparation and in combination with metformin (Avandamet). Another combination drug approved by the FDA is Avandaryl (with glimepiride); Like other thiazolidinediones, its mechanism of action is by activation of the intracellular receptor class of the peroxisome proliferator-activated receptors (PPARs), specifically PPAR-gamma. Rosiglitazone is a pure ligand of PPAR-gamma, and has no PPAR-alpha binding action. Apart from its effect on insulin resistance, it appears to have an anti-inflammatory effect: nuclear factor kappa-B (NFkB) levels fall and inhibitor (IkB) levels increase in patients on rosiglitazone (Mohanty et al). It increases glyceroneogenesis and reduces the release of free fatty acids from adipocytes.
Structure
Data?1582752341
Synonyms
ValueSource
5-((4-(2-(Methyl-2-pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedioneChEBI
BRL-49653ChEBI
RosiglitazonaChEBI
RosiglitazonumChEBI
GaudilKegg
AvandiaHMDB
Rosiglitazone maleateHMDB
RosiglizoleHMDB
5-((4-(2-Methyl-2-(pyridinylamino)ethoxy)phenyl)methyl)-2,4-thiazolidinedione-2-butenedioateHMDB
GlaxoSmithKline brand OF rosiglitazone maleateHMDB
SmithKline beecham brand OF rosiglitazone maleateHMDB
Glaxo wellcome brand OF rosiglitazone maleateHMDB
Chemical FormulaC18H19N3O3S
Average Molecular Weight357.427
Monoisotopic Molecular Weight357.114712179
IUPAC Name5-[(4-{2-[methyl(pyridin-2-yl)amino]ethoxy}phenyl)methyl]-1,3-thiazolidine-2,4-dione
Traditional Namerosiglitazone
CAS Registry Number122320-73-4
SMILES
CN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N1
InChI Identifier
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)
InChI KeyYASAKCUCGLMORW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aminopyridine
  • Monocyclic benzene moiety
  • Pyridine
  • Imidolactam
  • Heteroaromatic compound
  • Meta-thiazoline
  • Carbonic acid derivative
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available172.62http://allccs.zhulab.cn/database/detail?ID=AllCCS00000747
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.038 g/LALOGPS
logP2.95ALOGPS
logP2.45ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.84ChemAxon
pKa (Strongest Basic)6.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.53 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.79 m³·mol⁻¹ChemAxon
Polarizability37.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.44831661259
DarkChem[M-H]-178.78431661259
DeepCCS[M+H]+177.97530932474
DeepCCS[M-H]-175.61730932474
DeepCCS[M-2H]-208.50330932474
DeepCCS[M+Na]+184.06830932474
AllCCS[M+H]+185.832859911
AllCCS[M+H-H2O]+182.932859911
AllCCS[M+NH4]+188.532859911
AllCCS[M+Na]+189.332859911
AllCCS[M-H]-184.232859911
AllCCS[M+Na-2H]-184.132859911
AllCCS[M+HCOO]-184.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RosiglitazoneCN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N14277.8Standard polar33892256
RosiglitazoneCN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N13210.3Standard non polar33892256
RosiglitazoneCN(CCOC1=CC=C(CC2SC(=O)NC2=O)C=C1)C1=CC=CC=N13296.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rosiglitazone,1TMS,isomer #1CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=CC=CC=N13273.2Semi standard non polar33892256
Rosiglitazone,1TMS,isomer #1CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=CC=CC=N13068.8Standard non polar33892256
Rosiglitazone,1TMS,isomer #1CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C)C2=O)C=C1)C1=CC=CC=N14246.2Standard polar33892256
Rosiglitazone,1TBDMS,isomer #1CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=CC=CC=N13494.7Semi standard non polar33892256
Rosiglitazone,1TBDMS,isomer #1CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=CC=CC=N13285.6Standard non polar33892256
Rosiglitazone,1TBDMS,isomer #1CN(CCOC1=CC=C(CC2SC(=O)N([Si](C)(C)C(C)(C)C)C2=O)C=C1)C1=CC=CC=N14234.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rosiglitazone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-6931000000-a3ad698c8739c8f57e742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rosiglitazone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Rosiglitazone LC-ESI-qTof , Positive-QTOFsplash10-0a4i-0109000000-d527d5c2b5f1de3522642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rosiglitazone , positive-QTOFsplash10-0a4i-0109000000-d527d5c2b5f1de3522642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rosiglitazone , positive-QTOFsplash10-0a4r-1609000000-585d240b82e4a1918a292017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rosiglitazone , positive-QTOFsplash10-0a4i-0309000000-a9fa2307075b611cffcc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rosiglitazone 35V, Negative-QTOFsplash10-0a4i-1009000000-991ab6592f05f0e9b3b42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Rosiglitazone 35V, Positive-QTOFsplash10-052r-0906000000-d2389ebced7cec4a890e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 10V, Positive-QTOFsplash10-0a4i-0119000000-afcd19b8a0a922a55f1a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 20V, Positive-QTOFsplash10-052r-0941000000-369864aa78ee259dca922016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 40V, Positive-QTOFsplash10-0a4i-1910000000-f9a7e77fcdf7ededf79c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 10V, Negative-QTOFsplash10-0a4i-0439000000-ab505f9372d95dd2a7622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 20V, Negative-QTOFsplash10-0k9l-4792000000-bfe60ce181bc6c7314cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 40V, Negative-QTOFsplash10-0006-9500000000-9699ab9cf1188cacce3f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 10V, Negative-QTOFsplash10-0a4i-1159000000-cd81e0c7b3e3f06313362021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 20V, Negative-QTOFsplash10-0006-9242000000-b5f05b953b17b8f5dc012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 40V, Negative-QTOFsplash10-0006-9100000000-1495c41f9621c21b07f32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 10V, Positive-QTOFsplash10-000i-0902000000-914f8b56c690e9af074d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 20V, Positive-QTOFsplash10-052r-0579000000-0ae28d63488de9c942ee2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rosiglitazone 40V, Positive-QTOFsplash10-05g0-0910000000-de9d0cd74d041cf2fe822021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00412
Phenol Explorer Compound IDNot Available
FooDB IDFDB023598
KNApSAcK IDNot Available
Chemspider ID70383
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRosiglitazone
METLIN IDNot Available
PubChem Compound77999
PDB IDNot Available
ChEBI ID50122
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceManne Reddy, "Amorphous form of rosiglitazone maleate and process for preparation thereof." U.S. Patent US20040242658, issued December 02, 2004.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
General function:
Involved in DNA binding
Specific function:
Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular weight:
57619.6