D0026 | Ciglitazone

Molecular Formula C18H23NO3S
Molecular Weight 333.4
State solid
Description prototypical compound for the thiazolidinedione class; PPARgamma ligand; anti-hyperglycemic

Toxicity Dose Time Species Model Method Action Positive criterion Reference
TRANSMEMBRANE POTENTIAL 10–50 μM 3min male CD-1 mice isolated liver mitochondria The electrical transmembrane potential of mitochondria was monitored spectrophotometrically with the cationic dye, rhodamine 123, and monitored at the 505/535 nm. decrease p < 0.05, significantly different from the control 331
OPENING OF PERMEABILITY TRANSITION PORE (PTP) 10–75 μM male CD-1 mice isolated liver mitochondria Mitochondrial swelling as the indicator of mitochondrial permeability transition (MPT) was estimated from the decrease in absorbance at 540 nm. induce 331
MEMBRANE POTENTIAL 8.22±1.60 human qHTS-HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 14.13 human HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 9.92±4.25 rat hepatocytes MMP assay decrease IC50 163
OXYGEN CONSUMPTION RATE (OCR) > 100 μM 2 minutes human HepG2 Measurement of ECAR decrease EC50 7
OXYGEN CONSUMPTION RATE (OCR) > 100 μM 2 minutes feline cardiomyocytes Measurement of OCR decrease EC50 7
ECAR > 100 μM 2 minutes human HepG2 Measurement of ECAR increase EC50 7
ECAR 10 μM 2 minutes feline cardiomyocytes Measurement of ECAR increase EC50 7
ACCUMULATION OF CALCIUM 50 μM male CD-1 mice isolated liver mitochondria Assessment of mitochondrial Ca2+ efflux with arsenazo III at 675/685 nm. decrease 331

Pictogram Signal Statements Precautionary Statement Codes

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P201, P202, P281, P308+P313, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

  • (+-)-5-(p-((1-Methylcyclohexyl)methoxy)benzyl)-2,4-thiazolidinedione (+/-)-5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione 2,4-Thiazolidinedione, 5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-
    2,4-Thiazolidinedione, 5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-, (+-)- 2,4-Thiazolidinedione, 5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]- 5-((4-((1-methylcyclohexyl)methoxy)phenyl)methyl)-4-thiazolidinedione
    5-(4-((1-methylcyclohexyl)methoxy)benzyl)thiazolidine-2,4-dione 5-(4-(1-methylcyclohexylmethoxy)benzyl)thiazolidine-2,4-dione 5-({4-[(methylcyclohexyl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
    5-[4-(1-methylcyclohexylmethyloxy)benzyl]thiazolidine-2,4-dione 5-[[4-[(1-Methylcyclohexyl)methoxy]phenyl]methyl]-2,4-thiazolidinedione 5-[[4-[(1-methylcyclohexyl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
    5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione 74772-77-3 ACMC-20emv7
    ADD 3878 ADD-3878 AKOS000278268
    AKOS024257650 API0002009 AS-56269
    BCBcMAP01_000122 BDBM50103636 BML2-F01
    BRD-A93000692-001-02-4 BRD-A93000692-001-03-2 BSPBio_001575
    Bio1_000144 Bio1_000633 Bio1_001122
    Bio2_000295 Bio2_000775 C-20127
    C18H23NO3S CAS-74772-77-3 CBiol_001858
    CC-25778 CHEBI:64227 CTK7H5565
    Ciglitazona Ciglitazona [Spanish] Ciglitazone (USAN/INN)
    Ciglitazone [USAN:INN] Ciglitazonum Ciglitazonum [Latin]
    Ciglitizone Ciglitizone, >=98% (HPLC) D03493
    DB-055908 DB09201 DSSTox_CID_20757
    DSSTox_GSID_40757 DSSTox_RID_79589 DTXSID0040757
    FT-0602959 GL8018 GTPL2711
    HMS1361O17 HMS1791O17 HMS1989O17
    HMS3267N05 HMS3402O17 HMS3412E22
    HMS3649G06 HMS3676E22 IDI1_034045
    KBio2_000295 KBio2_002863 KBio2_005431
    KBio3_000589 KBio3_000590 KBioGR_000295
    KBioSS_000295 KS-0000008X LO4
    LS-151334 MCULE-4419123362 MFCD00865499
    NCGC00025104-02 NCGC00025104-03 NCGC00025104-04
    NCGC00025104-05 NCGC00025104-07 NCGC00025104-08
    NCGC00025104-09 NCGC00164446-01 Q5119890
    SC-50312 SCHEMBL38185 SR-01000597400
    SR-01000597400-1 SR-01000597400-3 SR-01000597400-4
    ST079285 Spectrum5_001949 TRA0078629
    TX-017480 Tox21 112120 Tox21_112120
    Tox21_112120_1 U 63287 U-63287
    UPCMLD-DP145 UPCMLD-DP145:001 UPCMLD-DP145:002

    DrugBank Name Ciglitazone
    DrugBank DB09201
    CAS Number 74772-77-3, 85010-66-8
    PubChem Compound 2750
    KEGG Drug D03493
    PubChem.Substance 310265109
    ChEBI 64227
    ChemSpider 2648
    BindingDB 50103636.0
    Wikipedia Ciglitazone

    1. Chan et al. (2005)