ROSIGLITAZONE MALEATE

Search structure
Trade Names:
Synonyms:
Status: Approved (1999) Withdrawn (2010)
Entry Type: Small molecule
Molecule Category: Parent
UNII: KX2339DP44

Structure
InChI Key SUFUKZSWUHZXAV-BTJKTKAUSA-N
Smile CN(CCOc1ccc(CC2SC(=O)NC2=O)cc1)c1ccccn1.O=C(O)/C=C\C(=O)O
InChI
InChI=1S/C18H19N3O3S.C4H4O4/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;5-3(6)1-2-4(7)8/h2-9,15H,10-12H2,1H3,(H,20,22,23);1-2H,(H,5,6)(H,7,8)/b;2-1-

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H23N3O7S
Molecular Weight 473.51
AlogP 2.49
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 7.0
Polar Surface Area 71.53
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 25.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Peroxisome proliferator-activated receptor gamma agonist DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 3
- - - 10000 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group C Nuclear hormone receptor subfamily 1 group C member 3
730 - - 14-136 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 1
- - 15010 - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Diabetes Mellitus, Type 2 4 D003924 ClinicalTrials
Insulin Resistance 3 D007333 ClinicalTrials
Atherosclerosis 3 D050197 ClinicalTrials
Head and Neck Neoplasms 2 D006258 ClinicalTrials
Pituitary ACTH Hypersecretion 2 D047748 ClinicalTrials
Non-alcoholic Fatty Liver Disease 2 D065626 ClinicalTrials
Central Nervous System Neoplasms 2 D016543 ClinicalTrials
Leukoplakia, Oral 2 D007972 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Heart Failure 2 D006333 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials

Related Entries

MCS

Scaffolds

Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Diarrhoea 35.0
Nervous system disorders Headache 20.0
Gastrointestinal disorders Diarrhoea 15.6
Endocrine disorders Hypoglycaemia 13.0
Infections and infestations Sinusitis 12.0
Endocrine disorders Hyperglycaemia 10.0
Infections and infestations Upper respiratory tract infection 9.9
General disorders and administration site conditions Asthenia 9.0
Musculoskeletal and connective tissue disorders Back pain 9.0
General disorders and administration site conditions Fatigue 9.0
Nervous system disorders Headache 8.9
Infections and infestations Upper respiratory tract infection 8.9
Infections and infestations Upper respiratory tract infection
Endocrine disorders Hyperglycaemia 8.1
Infections and infestations Upper respiratory tract infection 7.3
Blood and lymphatic system disorders Anaemia 7.1
Infections and infestations Nasopharyngitis 6.9
Gastrointestinal disorders Diarrhoea 6.8
Infections and infestations Nasopharyngitis 6.6
Infections and infestations Nasopharyngitis 6.3
Vascular disorders Hypertension 6.1
Vascular disorders Hypertension 6.0
Nervous system disorders Headache 5.9
Endocrine disorders Hypoglycaemia 5.9
Endocrine disorders Hyperglycaemia
Nervous system disorders Headache 5.4
Musculoskeletal and connective tissue disorders Back pain 5.3
Infections and infestations Sinusitis 5.3
Musculoskeletal and connective tissue disorders Back pain 5.1
Musculoskeletal and connective tissue disorders Arthralgia 5.0
General disorders and administration site conditions Asthenia
Musculoskeletal and connective tissue disorders Back pain 5.0
General disorders and administration site conditions Fatigue
Nervous system disorders Headache
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 5.0
Infections and infestations Upper respiratory tract infection 5.0
Musculoskeletal and connective tissue disorders Back pain 4.9
Musculoskeletal and connective tissue disorders Arthralgia 4.8
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.8
Infections and infestations Upper respiratory tract infection 4.7
Infections and infestations Sinusitis
Endocrine disorders Hyperglycaemia 4.4
Vascular disorders Hypertension 4.4
Infections and infestations Upper respiratory tract infection 4.3
Musculoskeletal and connective tissue disorders Arthralgia 4.2
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 4.2
General disorders and administration site conditions Asthenia 4.0
Musculoskeletal and connective tissue disorders Back pain 4.0
General disorders and administration site conditions Fatigue 4.0
Endocrine disorders Hyperglycaemia 3.9
Musculoskeletal and connective tissue disorders Back pain
General disorders and administration site conditions Asthenia 3.6
General disorders and administration site conditions Fatigue 3.6
Endocrine disorders Hypoglycaemia 3.4
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 3.2
Infections and infestations Sinusitis 3.2
Gastrointestinal disorders Diarrhoea 3.0
Endocrine disorders Hypoglycaemia 3.0
Infections and infestations Sinusitis 3.0
Endocrine disorders Hypoglycaemia 2.9
Gastrointestinal disorders Diarrhoea 2.5
Gastrointestinal disorders Diarrhoea 2.3
General disorders and administration site conditions Asthenia 1.9
General disorders and administration site conditions Fatigue 1.9
Endocrine disorders Hypoglycaemia 1.3
Endocrine disorders Hypoglycaemia 1.0
Endocrine disorders Hypoglycaemia 0.6
Endocrine disorders Hypoglycaemia

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Cardiac disorders
42.52
Vascular disorders
36.91
Nervous system disorders
9.79
Surgical and medical procedures
3.96
Respiratory, thoracic and mediastinal disorders
2.06

Cross References

Resources Reference
ChEBI 8892
ChEMBL CHEMBL843
EPA CompTox DTXSID2023569
FDA SRS KX2339DP44
PubChem 5281055
SureChEMBL SCHEMBL19023
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