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Identification
NameTroglitazone
Accession NumberDB00197  (APRD00488)
TypeSmall Molecule
GroupsWithdrawn
DescriptionTroglitazone was withdrawn in 2000 due to risk of hepatotoxicity. It was superseded by pioglitazone and rosiglitazone.
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NoscalNot Available
ResulinNot Available
RezulinNot Available
RomozinNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIII66ZZ0ZN0E
CAS number97322-87-7
WeightAverage: 441.54
Monoisotopic: 441.160993669
Chemical FormulaC24H27NO5S
InChI KeyGXPHKUHSUJUWKP-UHFFFAOYSA-N
InChI
InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,9-12H2,1-4H3,(H,25,27,28)
IUPAC Name
5-({4-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl)methoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
SMILES
CC1=C(C)C2=C(CCC(C)(COC3=CC=C(CC4SC(=O)NC4=O)C=C3)O2)C(C)=C1O
Pharmacology
IndicationFor the treatment of Type II diabetes mellitus. It is used alone or in combination with a sulfonylurea, metformin, or insulin as an adjunct to diet and exercise.
Structured Indications Not Available
PharmacodynamicsTroglitazone is an oral antihyperglycemic agent which acts primarily by decreasing insulin resistance. Troglitazone is used in the management of type II diabetes (noninsulin-dependent diabetes mellitus (NIDDM) also known as adult-onset diabetes). It improves sensitivity to insulin in muscle and adipose tissue and inhibits hepatic gluconeogenesis. Troglitazone is not chemically or functionally related to either the sulfonylureas, the biguanides, or the g-glucosidase inhibitors. Troglitazone may be used concomitantly with a sulfonylurea or insulin to improve glycemic control.
Mechanism of actionTroglitazone is a thiazolidinedione antidiabetic agent that lowers blood glucose by improving target cell response to insulin. It has a unique mechanism of action that is dependent on the presence of insulin for activity. Troglitazone decreases hepatic glucose output and increases insulin dependent glucose disposal in skeletal muscle. Its mechanism of action is thought to involve binding to nuclear receptors (PPAR) that regulate the transcription of a number of insulin responsive genes critical for the control of glucose and lipid metabolism. Troglitazone is a ligand to both PPARα and PPARγ, with a highter affinity for PPARγ. The drug also contains an α-tocopheroyl moiety, potentially giving it vitamin E-like activity. Troglitazone has been shown to reduce inflammation, and is associated with a decrase in nuclear factor kappa-B (NF-κB) and a concomitant increase in its inhibitor (IκB). NF-κB is an important cellular transcription regulator for the immune response. Unlike sulfonylureas, troglitazone is not an insulin secretagogue.
TargetKindPharmacological actionActionsOrganismUniProt ID
Peroxisome proliferator-activated receptor gammaProteinyes
agonist
HumanP37231 details
Long-chain-fatty-acid--CoA ligase 4Proteinno
inhibitor
HumanO60488 details
Plasminogen activator inhibitor 1Proteinunknown
antagonist
HumanP05121 details
Equilibrative nucleoside transporter 1Proteinno
inhibitor
HumanQ99808 details
Estrogen-related receptor gammaProteinno
inverse agonist
HumanP62508 details
Steroid hormone receptor ERR1Proteinno
inverse agonist
HumanP11474 details
Related Articles
AbsorptionAbsorbed rapidly. Food increases the extent of absorption by 30% to 85%.
Volume of distributionNot Available
Protein binding> 99% (primarily to serum albumin)
Metabolism

A sulfate conjugate metabolite (Metabolite 1) and a quinone metabolite (Metabolite 3) have been detected in the plasma of healthy males. A glucuronide conjugate (Metabolite 2) has been detected in the urine and also in negligible amounts in the plasma. In healthy volunteers and in patients with type 2 diabetes, the steady-state concentration of Metabolite 1 is six to seven times that of troglitazone and Metabolite 3. In in vivo drug interaction studies, troglitazone has been shown to induce cytochrome P450 CYP3A4 at clinically relevant doses.

Route of eliminationNot Available
Half life16-34 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Troglitazone can be increased when it is combined with Abiraterone.Approved
AcetohexamideTroglitazone may increase the hypoglycemic activities of Acetohexamide.Withdrawn
AmiodaroneThe metabolism of Troglitazone can be decreased when combined with Amiodarone.Approved, Investigational
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Troglitazone.Approved
AprepitantThe serum concentration of Troglitazone can be increased when it is combined with Aprepitant.Approved, Investigational
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Troglitazone.Approved, Investigational
ArmodafinilThe metabolism of Troglitazone can be decreased when combined with Armodafinil.Approved, Investigational
Arsenic trioxideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Arsenic trioxide.Approved, Investigational
ArticaineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Articaine.Approved
AsenapineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Asenapine.Approved
AtazanavirThe metabolism of Troglitazone can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Troglitazone can be decreased when combined with Atomoxetine.Approved
BendroflumethiazideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Bendroflumethiazide.Approved
BetamethasoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Betamethasone.Approved, Vet Approved
BexaroteneThe serum concentration of Troglitazone can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Troglitazone can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Troglitazone can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Troglitazone can be decreased when it is combined with Bosentan.Approved, Investigational
BrexpiprazoleThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Brexpiprazole.Approved
BumetanideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Bumetanide.Approved
BuserelinThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Buserelin.Approved
CapecitabineThe metabolism of Troglitazone can be decreased when combined with Capecitabine.Approved, Investigational
CarbamazepineThe metabolism of Troglitazone can be increased when combined with Carbamazepine.Approved, Investigational
CelecoxibThe metabolism of Troglitazone can be decreased when combined with Celecoxib.Approved, Investigational
CeritinibThe serum concentration of Troglitazone can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Troglitazone can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChlorothiazideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Chlorothiazide.Approved, Vet Approved
ChlorpropamideTroglitazone may increase the hypoglycemic activities of Chlorpropamide.Approved
ChlorthalidoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Chlorthalidone.Approved
CholecalciferolThe metabolism of Troglitazone can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
Cholic AcidTroglitazone may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Troglitazone.Approved
CimetidineThe metabolism of Troglitazone can be decreased when combined with Cimetidine.Approved
CitalopramThe metabolism of Troglitazone can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Troglitazone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Troglitazone can be decreased when combined with Clemastine.Approved
ClopidogrelThe metabolism of Troglitazone can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClotrimazoleThe metabolism of Troglitazone can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Clozapine.Approved
CobicistatThe metabolism of Troglitazone can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Troglitazone can be increased when it is combined with Conivaptan.Approved, Investigational
CorticotropinThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Corticotropin.Approved, Vet Approved
Cortisone acetateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Cortisone acetate.Approved
CrizotinibThe metabolism of Troglitazone can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Troglitazone can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Troglitazone can be decreased when it is combined with Dabrafenib.Approved
DanazolThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Danazol.Approved
DarunavirThe metabolism of Troglitazone can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Troglitazone can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Troglitazone can be decreased when it is combined with Deferasirox.Approved, Investigational
DeferiproneThe serum concentration of Deferiprone can be increased when it is combined with Troglitazone.Approved
DelavirdineThe metabolism of Troglitazone can be decreased when combined with Delavirdine.Approved
DesogestrelThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Desogestrel.Approved
DexamethasoneThe serum concentration of Troglitazone can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DiazoxideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Diazoxide.Approved
DienogestThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Dienogest.Approved
DihydroergotamineThe metabolism of Troglitazone can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Troglitazone can be decreased when combined with Diltiazem.Approved
DisopyramideTroglitazone may increase the hypoglycemic activities of Disopyramide.Approved
DoxycyclineThe metabolism of Troglitazone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Troglitazone can be decreased when combined with Dronedarone.Approved
DrospirenoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Drospirenone.Approved
EfavirenzThe serum concentration of Troglitazone can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Troglitazone can be decreased when it is combined with Enzalutamide.Approved
EpinephrineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Epinephrine.Approved, Vet Approved
ErythromycinThe metabolism of Troglitazone can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Troglitazone can be decreased when it is combined with Eslicarbazepine acetate.Approved
EsomeprazoleThe metabolism of Troglitazone can be decreased when combined with Esomeprazole.Approved, Investigational
EstradiolThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Estradiol.Approved, Investigational, Vet Approved
Estrone sulfateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Estrone sulfate.Approved
Etacrynic acidThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Etacrynic acid.Approved
Ethinyl EstradiolThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Ethinyl Estradiol.Approved
Ethynodiol diacetateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Ethynodiol diacetate.Approved
EtonogestrelThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Etonogestrel.Approved, Investigational
EtravirineThe serum concentration of Troglitazone can be decreased when it is combined with Etravirine.Approved
EverolimusThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Everolimus.Approved
FelodipineThe metabolism of Troglitazone can be decreased when combined with Felodipine.Approved, Investigational
FloxuridineThe metabolism of Troglitazone can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Troglitazone can be decreased when combined with Fluconazole.Approved
FludrocortisoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Fludrocortisone.Approved
FluorouracilThe metabolism of Troglitazone can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Troglitazone can be decreased when combined with Fluoxetine.Approved, Vet Approved
FluvastatinThe metabolism of Troglitazone can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Troglitazone can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Troglitazone can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Troglitazone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Troglitazone can be increased when combined with Fosphenytoin.Approved
FurosemideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Furosemide.Approved, Vet Approved
Fusidic AcidThe serum concentration of Troglitazone can be increased when it is combined with Fusidic Acid.Approved
GemfibrozilThe metabolism of Troglitazone can be decreased when combined with Gemfibrozil.Approved
GlibornurideTroglitazone may increase the hypoglycemic activities of Glibornuride.Withdrawn
GliclazideTroglitazone may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideTroglitazone may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideTroglitazone may increase the hypoglycemic activities of Glipizide.Approved
GliquidoneTroglitazone may increase the hypoglycemic activities of Gliquidone.Approved
GlisoxepideTroglitazone may increase the hypoglycemic activities of Glisoxepide.Approved
GlyburideTroglitazone may increase the hypoglycemic activities of Glyburide.Approved
GoserelinThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Goserelin.Approved
HistrelinThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Histrelin.Approved
HydrochlorothiazideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Hydrochlorothiazide.Approved, Vet Approved
HydrocortisoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Hydrocortisone.Approved, Vet Approved
HydroflumethiazideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Hydroflumethiazide.Approved
Hydroxyprogesterone caproateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Hydroxyprogesterone caproate.Approved
IdelalisibThe serum concentration of Troglitazone can be increased when it is combined with Idelalisib.Approved
IloperidoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Iloperidone.Approved
ImatinibThe metabolism of Troglitazone can be decreased when combined with Imatinib.Approved
IndapamideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Indapamide.Approved
IndinavirThe metabolism of Troglitazone can be decreased when combined with Indinavir.Approved
Insulin AspartTroglitazone may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirTroglitazone may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineTroglitazone may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineTroglitazone may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanTroglitazone may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproTroglitazone may increase the hypoglycemic activities of Insulin Lispro.Approved
IrbesartanThe metabolism of Troglitazone can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Troglitazone can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoniazidThe metabolism of Troglitazone can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Troglitazone can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Troglitazone can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Troglitazone can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Troglitazone can be decreased when combined with Ketoconazole.Approved, Investigational
LanreotideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Lanreotide.Approved
LapatinibThe metabolism of Troglitazone can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe metabolism of Troglitazone can be decreased when combined with Leflunomide.Approved, Investigational
LeuprolideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Leuprolide.Approved, Investigational
LevonorgestrelThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Levonorgestrel.Approved, Investigational
Lipoic AcidLipoic Acid may increase the hypoglycemic activities of Troglitazone.Approved, Nutraceutical
LopinavirThe metabolism of Troglitazone can be decreased when combined with Lopinavir.Approved
LosartanThe metabolism of Troglitazone can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Troglitazone can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Troglitazone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Troglitazone can be increased when it is combined with Lumacaftor.Approved
LurasidoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Lurasidone.Approved
MecaserminTroglitazone may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
Medroxyprogesterone acetateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Medroxyprogesterone acetate.Approved, Investigational
Megestrol acetateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Megestrol acetate.Approved, Vet Approved
MestranolThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Mestranol.Approved
MethotrimeprazineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Methotrimeprazine.Approved
MethyclothiazideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Methyclothiazide.Approved
MethylprednisoloneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Methylprednisolone.Approved, Vet Approved
MetolazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Metolazone.Approved
MifepristoneThe serum concentration of Troglitazone can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Troglitazone can be decreased when it is combined with Mitotane.Approved
MoclobemideThe metabolism of Troglitazone can be decreased when combined with Moclobemide.Approved
ModafinilThe serum concentration of Troglitazone can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Troglitazone can be decreased when it is combined with Nafcillin.Approved
NateglinideTroglitazone may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NefazodoneThe metabolism of Troglitazone can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Troglitazone can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Troglitazone can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Troglitazone can be increased when combined with Nevirapine.Approved
NiacinThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Niacin.Approved, Investigational, Nutraceutical
NicardipineThe metabolism of Troglitazone can be decreased when combined with Nicardipine.Approved
NilotinibThe metabolism of Troglitazone can be decreased when combined with Nilotinib.Approved, Investigational
NorethisteroneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Norethisterone.Approved
NorgestimateThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Norgestimate.Approved
OctreotideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Octreotide.Approved, Investigational
OlanzapineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Olanzapine.Approved, Investigational
OlaparibThe metabolism of Troglitazone can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Troglitazone can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Troglitazone can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Troglitazone can be increased when it is combined with Palbociclib.Approved
PaliperidoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Paliperidone.Approved
PantoprazoleThe metabolism of Troglitazone can be decreased when combined with Pantoprazole.Approved
PasireotideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Pasireotide.Approved
PentamidineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Pentamidine.Approved
PentobarbitalThe metabolism of Troglitazone can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Troglitazone can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Troglitazone can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneThe metabolism of Troglitazone can be decreased when combined with Pioglitazone.Approved, Investigational
PiperazineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Piperazine.Approved, Vet Approved
PipotiazineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Pipotiazine.Approved
PolythiazideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Polythiazide.Approved
PosaconazoleThe metabolism of Troglitazone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PrednisoloneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Prednisolone.Approved, Vet Approved
PrednisoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Prednisone.Approved, Vet Approved
PregabalinPregabalin may increase the fluid retaining activities of Troglitazone.Approved, Illicit, Investigational
PrimidoneThe metabolism of Troglitazone can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Progesterone.Approved, Vet Approved
PyrimethamineThe metabolism of Troglitazone can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuetiapineThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Quetiapine.Approved
QuinethazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Quinethazone.Approved
QuinineThe metabolism of Troglitazone can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Troglitazone can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe metabolism of Troglitazone can be decreased when combined with Ranolazine.Approved, Investigational
RepaglinideTroglitazone may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RifabutinThe metabolism of Troglitazone can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Troglitazone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Troglitazone can be increased when combined with Rifapentine.Approved
RisperidoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Risperidone.Approved, Investigational
RitonavirThe metabolism of Troglitazone can be decreased when combined with Ritonavir.Approved, Investigational
RosiglitazoneThe metabolism of Troglitazone can be decreased when combined with Rosiglitazone.Approved, Investigational
SaquinavirThe metabolism of Troglitazone can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Troglitazone.Approved
SecobarbitalThe metabolism of Troglitazone can be increased when combined with Secobarbital.Approved, Vet Approved
SertralineThe metabolism of Troglitazone can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Troglitazone can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Troglitazone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Troglitazone can be increased when it is combined with Simeprevir.Approved
SirolimusThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Sirolimus.Approved, Investigational
SorafenibThe metabolism of Troglitazone can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Troglitazone can be decreased when it is combined with St. John's Wort.Nutraceutical
StiripentolThe serum concentration of Troglitazone can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Troglitazone can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Troglitazone can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Troglitazone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SunitinibTroglitazone may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TacrolimusThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Tacrolimus.Approved, Investigational
TamoxifenThe metabolism of Troglitazone can be decreased when combined with Tamoxifen.Approved
TelaprevirThe metabolism of Troglitazone can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Troglitazone can be decreased when combined with Telithromycin.Approved
TemsirolimusThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Temsirolimus.Approved
TeriflunomideThe metabolism of Troglitazone can be decreased when combined with Teriflunomide.Approved
TicagrelorThe metabolism of Troglitazone can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Troglitazone can be decreased when combined with Ticlopidine.Approved
TipranavirThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Tipranavir.Approved, Investigational
TocilizumabThe serum concentration of Troglitazone can be decreased when it is combined with Tocilizumab.Approved
TolazamideTroglitazone may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideTroglitazone may increase the hypoglycemic activities of Tolbutamide.Approved
TopiramateThe metabolism of Troglitazone can be decreased when combined with Topiramate.Approved
TorasemideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Torasemide.Approved
TranylcypromineThe metabolism of Troglitazone can be decreased when combined with Tranylcypromine.Approved
TriamcinoloneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Triamcinolone.Approved, Vet Approved
TrichlormethiazideThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Trichlormethiazide.Approved, Vet Approved
TrimethoprimThe metabolism of Troglitazone can be decreased when combined with Trimethoprim.Approved, Vet Approved
TriptorelinThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Triptorelin.Approved, Vet Approved
Valproic AcidThe metabolism of Troglitazone can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Troglitazone can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe metabolism of Troglitazone can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Troglitazone can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Troglitazone can be decreased when combined with Voriconazole.Approved, Investigational
VorinostatThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Vorinostat.Approved, Investigational
ZafirlukastThe metabolism of Troglitazone can be decreased when combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe metabolism of Troglitazone can be decreased when combined with Ziprasidone.Approved
Food InteractionsNot Available
References
Synthesis Reference

Krishnamurthi Vyas, Chebiyyam Prabhakar, Sreenivas Dharmaraja Rao, Mamillapalli Ramabadhra Sarma, Om Gaddam Reddy, Rajagopalan Ramanujam, Ranjan Chakrabarti, “Polymorphic forms of troglitazone having enhanced anti-diabetic activity and a process for their preparation.” U.S. Patent US5700820, issued June, 1992.

US5700820
General References
  1. Aljada A, Garg R, Ghanim H, Mohanty P, Hamouda W, Assian E, Dandona P: Nuclear factor-kappaB suppressive and inhibitor-kappaB stimulatory effects of troglitazone in obese patients with type 2 diabetes: evidence of an antiinflammatory action? J Clin Endocrinol Metab. 2001 Jul;86(7):3250-6. [PubMed:11443197 ]
External Links
ATC CodesA10BG01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (501 KB)
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.868
Blood Brain Barrier+0.8183
Caco-2 permeable-0.6915
P-glycoprotein substrateSubstrate0.7514
P-glycoprotein inhibitor INon-inhibitor0.7854
P-glycoprotein inhibitor IINon-inhibitor0.7015
Renal organic cation transporterNon-inhibitor0.861
CYP450 2C9 substrateNon-substrate0.8329
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7408
CYP450 1A2 substrateNon-inhibitor0.5726
CYP450 2C9 inhibitorNon-inhibitor0.6843
CYP450 2D6 inhibitorNon-inhibitor0.9266
CYP450 2C19 inhibitorNon-inhibitor0.6359
CYP450 3A4 inhibitorNon-inhibitor0.5517
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5121
Ames testNon AMES toxic0.584
CarcinogenicityNon-carcinogens0.9211
BiodegradationNot ready biodegradable0.9881
Rat acute toxicity1.9768 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9911
hERG inhibition (predictor II)Non-inhibitor0.6643
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Sankyo usa corp
  • Pfizer pharmaceuticals ltd
Packagers
Dosage formsNot Available
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5602133 No1993-09-152013-09-15Us
US5859037 No1997-11-132017-11-13Us
US6011049 No1997-11-132017-11-13Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point184-186 °CNot Available
logP3.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00121 mg/mLALOGPS
logP4.16ALOGPS
logP5.5ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)6.61ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area84.86 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity120.99 m3·mol-1ChemAxon
Polarizability47.08 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct Parent1-benzopyrans
Alternative Parents
Substituents
  • 1-benzopyran
  • Phenol ether
  • Thiazolidinedione
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Thiazolidine
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Thioether
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation...
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular Weight:
57619.58 Da
References
  1. Kitamura S, Miyazaki Y, Shinomura Y, Kondo S, Kanayama S, Matsuzawa Y: Peroxisome proliferator-activated receptor gamma induces growth arrest and differentiation markers of human colon cancer cells. Jpn J Cancer Res. 1999 Jan;90(1):75-80. [PubMed:10076568 ]
  2. Demetri GD, Fletcher CD, Mueller E, Sarraf P, Naujoks R, Campbell N, Spiegelman BM, Singer S: Induction of solid tumor differentiation by the peroxisome proliferator-activated receptor-gamma ligand troglitazone in patients with liposarcoma. Proc Natl Acad Sci U S A. 1999 Mar 30;96(7):3951-6. [PubMed:10097144 ]
  3. Petrova TV, Akama KT, Van Eldik LJ: Cyclopentenone prostaglandins suppress activation of microglia: down-regulation of inducible nitric-oxide synthase by 15-deoxy-Delta12,14-prostaglandin J2. Proc Natl Acad Sci U S A. 1999 Apr 13;96(8):4668-73. [PubMed:10200320 ]
  4. Camp HS, Whitton AL, Tafuri SR: PPARgamma activators down-regulate the expression of PPARgamma in 3T3-L1 adipocytes. FEBS Lett. 1999 Mar 26;447(2-3):186-90. [PubMed:10214942 ]
  5. Satoh T, Furuta K, Suzuki M, Watanabe Y: Prostaglandin J2 and its metabolites promote neurite outgrowth induced by nerve growth factor in PC12 cells. Biochem Biophys Res Commun. 1999 Apr 29;258(1):50-3. [PubMed:10222233 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  7. Baek SJ, Wilson LC, Hsi LC, Eling TE: Troglitazone, a peroxisome proliferator-activated receptor gamma (PPAR gamma ) ligand, selectively induces the early growth response-1 gene independently of PPAR gamma. A novel mechanism for its anti-tumorigenic activity. J Biol Chem. 2003 Feb 21;278(8):5845-53. Epub 2002 Dec 9. [PubMed:12475986 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inhibitor
General Function:
Very long-chain fatty acid-coa ligase activity
Specific Function:
Activation of long-chain fatty acids for both synthesis of cellular lipids, and degradation via beta-oxidation. Preferentially uses arachidonate and eicosapentaenoate as substrates.
Gene Name:
ACSL4
Uniprot ID:
O60488
Molecular Weight:
79187.38 Da
References
  1. Kim JH, Lewin TM, Coleman RA: Expression and characterization of recombinant rat Acyl-CoA synthetases 1, 4, and 5. Selective inhibition by triacsin C and thiazolidinediones. J Biol Chem. 2001 Jul 6;276(27):24667-73. Epub 2001 Apr 23. [PubMed:11319222 ]
  2. Lewin TM, Van Horn CG, Krisans SK, Coleman RA: Rat liver acyl-CoA synthetase 4 is a peripheral-membrane protein located in two distinct subcellular organelles, peroxisomes, and mitochondrial-associated membrane. Arch Biochem Biophys. 2002 Aug 15;404(2):263-70. [PubMed:12147264 ]
  3. Lewin TM, Kim JH, Granger DA, Vance JE, Coleman RA: Acyl-CoA synthetase isoforms 1, 4, and 5 are present in different subcellular membranes in rat liver and can be inhibited independently. J Biol Chem. 2001 Jul 6;276(27):24674-9. Epub 2001 Apr 23. [PubMed:11319232 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Serine-type endopeptidase inhibitor activity
Specific Function:
Serine protease inhibitor. This inhibitor acts as 'bait' for tissue plasminogen activator, urokinase, protein C and matriptase-3/TMPRSS7. Its rapid interaction with PLAT may function as a major control point in the regulation of fibrinolysis.
Gene Name:
SERPINE1
Uniprot ID:
P05121
Molecular Weight:
45059.695 Da
References
  1. Sobel BE: Insulin resistance and thrombosis: a cardiologist's view. Am J Cardiol. 1999 Jul 8;84(1A):37J-41J. [PubMed:10418858 ]
  2. Gottschling-Zeller H, Rohrig K, Hauner H: Troglitazone reduces plasminogen activator inhibitor-1 expression and secretion in cultured human adipocytes. Diabetologia. 2000 Mar;43(3):377-83. [PubMed:10768100 ]
  3. Nordt TK, Peter K, Bode C, Sobel BE: Differential regulation by troglitazone of plasminogen activator inhibitor type 1 in human hepatic and vascular cells. J Clin Endocrinol Metab. 2000 Apr;85(4):1563-8. [PubMed:10770198 ]
  4. Kato K, Yamada D, Midorikawa S, Sato W, Watanabe T: Improvement by the insulin-sensitizing agent, troglitazone, of abnormal fibrinolysis in type 2 diabetes mellitus. Metabolism. 2000 May;49(5):662-5. [PubMed:10831180 ]
  5. Kruszynska YT, Yu JG, Olefsky JM, Sobel BE: Effects of troglitazone on blood concentrations of plasminogen activator inhibitor 1 in patients with type 2 diabetes and in lean and obese normal subjects. Diabetes. 2000 Apr;49(4):633-9. [PubMed:10871202 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inhibitor
General Function:
Nucleoside transmembrane transporter activity
Specific Function:
Mediates both influx and efflux of nucleosides across the membrane (equilibrative transporter). It is sensitive (ES) to low concentrations of the inhibitor nitrobenzylmercaptopurine riboside (NBMPR) and is sodium-independent. It has a higher affinity for adenosine. Inhibited by dipyridamole and dilazep (anticancer chemotherapeutics drugs).
Gene Name:
SLC29A1
Uniprot ID:
Q99808
Molecular Weight:
50218.805 Da
References
  1. Leung GP, Man RY, Tse CM: Effect of thiazolidinediones on equilibrative nucleoside transporter-1 in human aortic smooth muscle cells. Biochem Pharmacol. 2005 Aug 1;70(3):355-62. [PubMed:15963471 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inverse agonist
General Function:
Zinc ion binding
Specific Function:
Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response elements (By similarity). Induces the expression of PERM1 in the skeletal muscle.
Gene Name:
ESRRG
Uniprot ID:
P62508
Molecular Weight:
51305.485 Da
References
  1. Wang Y, Fang F, Wong CW: Troglitazone is an estrogen-related receptor alpha and gamma inverse agonist. Biochem Pharmacol. 2010 Jul 1;80(1):80-5. doi: 10.1016/j.bcp.2010.03.013. Epub 2010 Mar 16. [PubMed:20298676 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
inverse agonist
General Function:
Zinc ion binding
Specific Function:
Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and may act as an important regulator of MCAD promoter. Binds to the C1 region of the lactoferrin gene promoter. Requires dimerization and the coactivator, PGC-1A, for full activity. The ERRalpha/PGC1alp...
Gene Name:
ESRRA
Uniprot ID:
P11474
Molecular Weight:
45509.11 Da
References
  1. Wang Y, Fang F, Wong CW: Troglitazone is an estrogen-related receptor alpha and gamma inverse agonist. Biochem Pharmacol. 2010 Jul 1;80(1):80-5. doi: 10.1016/j.bcp.2010.03.013. Epub 2010 Mar 16. [PubMed:20298676 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitorinducer
General Function:
Vitamin d3 25-hydroxylase 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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naph...
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular Weight:
59590.91 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase 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...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Schoch GA, Yano JK, Sansen S, Dansette PM, Stout CD, Johnson EF: Determinants of cytochrome P450 2C8 substrate binding: structures of complexes with montelukast, troglitazone, felodipine, and 9-cis-retinoic acid. J Biol Chem. 2008 Jun 20;283(25):17227-37. doi: 10.1074/jbc.M802180200. Epub 2008 Apr 15. [PubMed:18413310 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxygen binding
Specific Function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular Weight:
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d 24-hydroxylase 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.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Steroid hydroxylase 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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase 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, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitorinducer
General Function:
Oxygen binding
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.
Gene Name:
CYP3A5
Uniprot ID:
P20815
Molecular Weight:
57108.065 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitorinducer
General Function:
Oxygen binding
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.
Gene Name:
CYP3A7
Uniprot ID:
P24462
Molecular Weight:
57525.03 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular Weight:
60337.835 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein homodimerization activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1 (By similarity).
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular Weight:
60024.535 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Protein homodimerization activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks transferase activity but acts as a negative regulator of isoform 1 (By similarity).
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular Weight:
60750.215 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
  2. Ito M, Yamamoto K, Sato H, Fujiyama Y, Bamba T: Inhibitory effect of troglitazone on glucuronidation catalyzed by human uridine diphosphate-glucuronosyltransferase 1A6. Eur J Clin Pharmacol. 2001 Mar;56(12):893-5. [PubMed:11317477 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A7
Uniprot ID:
Q9HAW7
Molecular Weight:
59818.315 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular Weight:
59741.035 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular Weight:
59940.495 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
  2. Barbier O, Villeneuve L, Bocher V, Fontaine C, Torra IP, Duhem C, Kosykh V, Fruchart JC, Guillemette C, Staels B: The UDP-glucuronosyltransferase 1A9 enzyme is a peroxisome proliferator-activated receptor alpha and gamma target gene. J Biol Chem. 2003 Apr 18;278(16):13975-83. Epub 2003 Feb 11. [PubMed:12582161 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Protein kinase c binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A10
Uniprot ID:
Q9HAW8
Molecular Weight:
59809.075 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol...
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular Weight:
60694.12 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Glucuronosyltransferase activity
Specific Function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidatio...
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular Weight:
61035.815 Da
References
  1. Watanabe Y, Nakajima M, Yokoi T: Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9. [PubMed:12433820 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Transporter activity
Specific Function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular Weight:
146405.83 Da
References
  1. Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
  2. Funk C, Pantze M, Jehle L, Ponelle C, Scheuermann G, Lazendic M, Gasser R: Troglitazone-induced intrahepatic cholestasis by an interference with the hepatobiliary export of bile acids in male and female rats. Correlation with the gender difference in troglitazone sulfate formation and the inhibition of the canalicular bile salt export pump (Bsep) by troglitazone and troglitazone sulfate. Toxicology. 2001 Oct 5;167(1):83-98. [PubMed:11557132 ]
  3. Saito H, Osumi M, Hirano H, Shin W, Nakamura R, Ishikawa T: Technical pitfalls and improvements for high-speed screening and QSAR analysis to predict inhibitors of the human bile salt export pump (ABCB11/BSEP). AAPS J. 2009 Sep;11(3):581-9. doi: 10.1208/s12248-009-9137-9. Epub 2009 Aug 18. [PubMed:19688600 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. Involved in the clearance of bile acids and organic anions from the liver.
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular Weight:
76447.99 Da
References
  1. Nozawa T, Sugiura S, Nakajima M, Goto A, Yokoi T, Nezu J, Tsuji A, Tamai I: Involvement of organic anion transporting polypeptides in the transport of troglitazone sulfate: implications for understanding troglitazone hepatotoxicity. Drug Metab Dispos. 2004 Mar;32(3):291-4. [PubMed:14977862 ]
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Drug created on June 13, 2005 07:24 / Updated on December 07, 2016 02:37