Identification

Name
Pioglitazone
Accession Number
DB01132  (APRD00653)
Type
Small Molecule
Groups
Approved, Investigational
Description

Pioglitazone is an antihyperglycemic used as an adjunct to diet, exercise, and other antidiabetic medications to manage type 2 diabetes mellitus.4,5,6,7 It is administered as a racemic mixture, though there is no pharmacologic difference between the enantiomers and they appear to interconvert in vivo with little consequence.4 The thiazolidinedione class of medications, which also includes rosiglitazone and troglitazone, exerts its pharmacological effect primarily by promoting insulin sensitivity and the improved uptake of blood glucose4 via agonism at the peroxisome proliferator-activated receptor-gamma (PPARγ).1 PPARs are ligand-activated transcription factors that are involved in the expression of more than 100 genes and affect numerous metabolic processes, most notably lipid and glucose homeostasis.2

Thiazolidinediones, including pioglitazone, have fallen out of favor in recent years due to the presence of multiple adverse effects and warnings regarding their use (e.g. congestive heart failure, bladder cancer) and the availability of safer and more effective alternatives for patients with type 2 diabetes mellitus.9

Structure
Thumb
Synonyms
  • (±)-5-((4-(2-(5-ethyl-2-pyridinyl)ethoxy)phenyl)methyl)-2,4-thiazolidinedione
  • 5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione
  • Pioglitazona
  • Pioglitazone
  • Pioglitazonum
External IDs
AD-4833 / U 72107A / U-72107A / U72107A
Product Ingredients
IngredientUNIICASInChI Key
Pioglitazone hydrochlorideJQT35NPK6C112529-15-4GHUUBYQTCDQWRA-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act PioglitazoneTabletOralTEVA Canada Limited2007-12-05Not applicableCanada
Act PioglitazoneTabletOralTEVA Canada Limited2007-12-05Not applicableCanada
Act PioglitazoneTabletOralTEVA Canada Limited2007-12-05Not applicableCanada
ActosTablet15 mgOralTakeda Pharma A/S2000-10-13Not applicableEu
ActosTablet30 mgOralTakeda Pharma A/S2000-10-13Not applicableEu
ActosTablet15 mg/1OralTakeda Pharmaceuticals America, Inc.1999-07-15Not applicableUs
ActosTablet15 mg/1OralMed Pharma Co., Ltd.2012-01-132012-04-05Us
ActosTablet15 mgOralTakeda Pharma A/S2000-10-13Not applicableEu
ActosTablet30 mgOralTakeda Pharma A/S2000-10-13Not applicableEu
ActosTablet45 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2012-02-172014-12-31Us
Additional Data Available
  • Application Number
    Application Number

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Accel PioglitazoneTabletOralAccel Pharma Inc2009-06-022020-03-20Canada
Accel PioglitazoneTabletOralAccel Pharma Inc2009-06-022020-03-20Canada
Accel PioglitazoneTabletOralAccel Pharma Inc2009-06-022020-03-20Canada
Ach-pioglitazoneTabletOralAccord Healthcare Inc2012-10-12Not applicableCanada
Ach-pioglitazoneTabletOralAccord Healthcare Inc2010-06-11Not applicableCanada
Ach-pioglitazoneTabletOralAccord Healthcare Inc2010-06-11Not applicableCanada
Ag-pioglitazoneTabletOralAngita Pharma Inc.Not applicableNot applicableCanada
Ag-pioglitazoneTabletOralAngita Pharma Inc.Not applicableNot applicableCanada
Apo-pioglitazoneTabletOralApotex Corporation2007-12-05Not applicableCanada
Apo-pioglitazoneTabletOralApotex Corporation2007-12-05Not applicableCanada
Additional Data Available
  • Application Number
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  • Product Code
    Product Code

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Actoplus MetPioglitazone hydrochloride (15 mg/1) + Metformin hydrochloride (850 mg/1)Tablet, film coatedOralTakeda Pharmaceuticals America, Inc.2005-08-29Not applicableUs
Actoplus MetPioglitazone hydrochloride (15 mg/1) + Metformin hydrochloride (500 mg/1)Tablet, film coatedOralTakeda Pharmaceuticals America, Inc.2005-08-29Not applicableUs
Actoplus MetPioglitazone hydrochloride (15 mg/1) + Metformin hydrochloride (850 mg/1)Tablet, film coatedOralCardinal Health2005-08-292014-05-31Us
Actoplus MetPioglitazone hydrochloride (15 mg/1) + Metformin hydrochloride (850 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2006-03-21Not applicableUs
Actoplus MetPioglitazone hydrochloride (15 mg/1) + Metformin hydrochloride (500 mg/1)Tablet, film coatedOralPhysicians Total Care, Inc.2006-01-04Not applicableUs
Actoplus Met XRPioglitazone hydrochloride (30 mg/1) + Metformin hydrochloride (1000 mg/1)Tablet, film coated, extended releaseOralTakeda Pharmaceuticals America, Inc.2010-06-112022-09-30Us
Actoplus Met XRPioglitazone hydrochloride (15 mg/1) + Metformin hydrochloride (1000 mg/1)Tablet, film coated, extended releaseOralTakeda Pharmaceuticals America, Inc.2010-06-112022-09-30Us
Alogliptin and PioglitazonePioglitazone hydrochloride (15 mg/1) + Alogliptin benzoate (12.5 mg/1)Tablet, film coatedOralPerrigo New York Inc2016-04-08Not applicableUs
Alogliptin and PioglitazonePioglitazone hydrochloride (30 mg/1) + Alogliptin benzoate (25 mg/1)Tablet, film coatedOralPerrigo New York Inc2016-04-08Not applicableUs
Alogliptin and PioglitazonePioglitazone hydrochloride (45 mg/1) + Alogliptin benzoate (25 mg/1)Tablet, film coatedOralPerrigo New York Inc2016-04-08Not applicableUs
International/Other Brands
Actost
Categories
UNII
X4OV71U42S
CAS number
111025-46-8
Weight
Average: 356.439
Monoisotopic: 356.119463206
Chemical Formula
C19H20N2O3S
InChI Key
HYAFETHFCAUJAY-UHFFFAOYSA-N
InChI
InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)
IUPAC Name
5-({4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}methyl)-1,3-thiazolidine-2,4-dione
SMILES
CCC1=CN=C(CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1

Pharmacology

Indication

Pioglitazone is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus.4 It is also available in combination with metformin,5 glimepiride,6 or alogliptin7 for the same indication.

Associated Conditions
Pharmacodynamics

Pioglitazone enhances cellular responsiveness to insulin, increases insulin-dependent glucose disposal, and improves impaired glucose homeostasis.1 In patients with type 2 diabetes mellitus, these effects result in lower plasma glucose concentrations, lower plasma insulin concentrations, and lower HbA1c values.1

Significant fluid retention leading to the development/exacerbation of congestive heart failure has been reported with pioglitazone - avoid its use in patients in heart failure or at risk of developing heart failure.4 There is some evidence that pioglitazone may be associated with an increased risk of developing bladder cancer. Pioglitazone should not be used in patients with active bladder cancer and should be used with caution in patients with a history of bladder cancer.4

Mechanism of action

Pioglitazone is a selective agonist at peroxisome proliferator-activated receptor-gamma (PPARγ) in target tissues for insulin action such as adipose tissue, skeletal muscle, and liver.4,2 Activation of PPARγ increases the transcription of insulin-responsive genes involved in the control of glucose and lipid production, transport, and utilization.2 Through this mechanism, pioglitazone both enhances tissue sensitivity to insulin and reduces the hepatic production of glucose (i.e. gluconeogenesis) - insulin resistance associated with type 2 diabetes mellitus is therefore improved without an increase in insulin secretion by pancreatic beta cells.4,2

TargetActionsOrganism
APeroxisome proliferator-activated receptor gamma
agonist
Humans
UAmine oxidase [flavin-containing] B
inhibitor
Humans
Additional Data Available
Adverse Effects

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Contraindications

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Blackbox Warnings

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Absorption

Following oral administration of pioglitazone, peak serum concentrations are observed within 2 hours (Tmax) - food slightly delays the time to peak serum concentration, increasing Tmax to approximately 3-4 hours, but does not alter the extent of absorption.4 Steady-state concentrations of both parent drug and its primary active metabolites are achieved after 7 days of once-daily administration of pioglitazone.4 Cmax and AUC increase proportionately to administered doses.4

Volume of distribution

The average apparent volume of distribution of pioglitazone is 0.63 ± 0.41 L/kg.4

Protein binding

Pioglitazone is >99% protein-bound in human plasma - binding is primarily to albumin, although pioglitazone has been shown to bind other serum proteins with a lower affinity.4 The M-III and M-IV metabolites of pioglitazone are >98% protein-bound (also primarily to albumin).4

Metabolism

Pioglitazone is extensively metabolized by both hydroxylation and oxidation - the resulting metabolites are also partly converted to glucuronide or sulfate conjugates.4 The pharmacologically active M-IV and M-III metabolites are the main metabolites found in human serum and their circulating concentrations are equal to, or greater than, those of the parent drug.3 The specific CYP isoenzymes involved in the metabolism of pioglitazone are CYP2C8 and, to a lesser degree, CYP3A4. There is also some evidence to suggest a contribution by extrahepatic CYP1A1.4

Route of elimination

Approximately 15-30% of orally administered pioglitazone is recovered in the urine. The bulk of its elimination, then, is presumed to be through the excretion of unchanged drug in the bile or as metabolites in the feces.4

Half life

The mean serum half-life of pioglitazone and its metabolites (M-III and M-IV) range from 3-7 hours and 16-24 hours, respectively.4

Clearance

The apparent clearance of orally administered pioglitazone is 5-7 L/h.4

Toxicity

The oral TDLo observed in mice is 24 mg/kg for 4 days and for rats is 3 mg/kg for 6 days.8

One instance of overdose was reported during clinical trials with pioglitazone in which a patient took an oral dose of 120mg daily for four days, followed by 180mg daily for seven days4 - this patient did not report any adverse clinical symptoms during this time. In the event of overdosage, employ symptomatic and supportive measures according to the patient's clinical status.4

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Pioglitazone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Pioglitazone.
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Pioglitazone is combined with 2,4-thiazolidinedione.
5-(2-methylpiperazine-1-sulfonyl)isoquinolineThe therapeutic efficacy of Pioglitazone can be increased when used in combination with 5-(2-methylpiperazine-1-sulfonyl)isoquinoline.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypoglycemic activities of Pioglitazone.
AbataceptThe metabolism of Pioglitazone can be increased when combined with Abatacept.
AbirateroneThe metabolism of Pioglitazone can be decreased when combined with Abiraterone.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Pioglitazone.
AcebutololThe therapeutic efficacy of Pioglitazone can be increased when used in combination with Acebutolol.
AcetazolamideThe therapeutic efficacy of Pioglitazone can be increased when used in combination with Acetazolamide.
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Food Interactions
  • Take with or without food. Food delays drug absorption, but not to a clinically significant extent.

References

Synthesis Reference

Chandra Khanduri, Yatendra Kumar, Atulya Panda, Suchitra Chakraborty, Mukesh Sharma, "Process for the preparation of pioglitazone." U.S. Patent US20070078170, issued April 05, 2007.

US20070078170
General References
  1. Al-Majed A, Bakheit AH, Abdel Aziz HA, Alharbi H, Al-Jenoobi FI: Pioglitazone. Profiles Drug Subst Excip Relat Methodol. 2016;41:379-438. doi: 10.1016/bs.podrm.2015.11.002. Epub 2016 Feb 2. [PubMed:26940171]
  2. Janani C, Ranjitha Kumari BD: PPAR gamma gene--a review. Diabetes Metab Syndr. 2015 Jan-Mar;9(1):46-50. doi: 10.1016/j.dsx.2014.09.015. Epub 2014 Oct 13. [PubMed:25450819]
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  4. FDA Approved Drug Products: Actos (pioglitazone) oral tablets [Link]
  5. FDA Approved Drug Products: Actoplus Met (pioglitazone/metformin) oral tablets [Link]
  6. FDA Approved Drug Products: Duetact (pioglitazone/glimepiride) oral tablets [Link]
  7. FDA Approved Drug Products: Oseni (pioglitazone/alogliptin) oral tablets [Link]
  8. CaymanChem: Pioglitazone MSDS [Link]
  9. Diabetes Canada: Clinical Practice Guidelines for Diabetes 2018 [Link]
External Links
Human Metabolome Database
HMDB0015264
KEGG Drug
D08378
KEGG Compound
C07675
PubChem Compound
4829
PubChem Substance
46507136
ChemSpider
4663
BindingDB
50103521
RxNav
33738
ChEBI
8228
ChEMBL
CHEMBL595
Therapeutic Targets Database
DAP000272
PharmGKB
PA450970
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pioglitazone
ATC Codes
A10BD09 — Pioglitazone and alogliptinA10BG03 — PioglitazoneA10BD05 — Metformin and pioglitazoneA10BD06 — Glimepiride and pioglitazoneA10BD12 — Pioglitazone and sitagliptin
AHFS Codes
  • 68:20.28 — Thiazolidinediones
FDA label
Download (61.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Active Not RecruitingTreatmentPioglitazone1
0CompletedBasic ScienceBMI >30 kg/m2 / Female Infertility1
0CompletedBasic ScienceLung Inflammation1
0CompletedBasic ScienceMetabolic Syndromes / Obese1
0CompletedBasic SciencePeripheral Arterial Disease (PAD)1
0CompletedTreatmentInfertility / Polycystic Ovaries Syndrome2
0CompletedTreatmentPolycystic Ovarian Syndrome1
0CompletedTreatmentPolycystic Ovaries Syndrome1
0RecruitingBasic ScienceBMI >30 kg/m21
0RecruitingTreatmentGastroparesis1
1Active Not RecruitingBasic ScienceInclusion Body Myositis (IBM) / Muscle Inflammation / Muscular Diseases / Musculoskeletal Disorders / Nervous System Diseases / Neuromuscular Diseases1
1Active Not RecruitingTreatmentProstatic Neoplasms, Castration-Resistant1
1CompletedNot AvailableBMI >30 kg/m2 / Insulin Resistance / Metabolic Syndromes1
1CompletedNot AvailableHealthy Volunteers6
1CompletedNot AvailableHealthy Volunteers / Pharmacokinetics of ASP19411
1CompletedBasic ScienceAmount of Pioglitazone in Blood / Drug Drug Interaction (DDI) / Healthy Volunteers / Pharmacokinetics / Pioglitazone / Rheumatoid Arthritis1
1CompletedBasic ScienceAutoimmune Pulmonary Alveolar Proteinosis1
1CompletedBasic ScienceHealthy Volunteers4
1CompletedOtherHealthy Volunteers2
1CompletedPreventionDiabetes1
1CompletedSupportive CareAnaplastic Astrocytoma (AA) / Brain Neoplasms, Benign / Brain Neoplasms, Malignant / Glioblastoma Multiforme (GBM) / Meningiomas malignant1
1CompletedTreatmentAdvanced Solid Tumors / Metastatic Solid Tumors1
1CompletedTreatmentAnemias1
1CompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m2 / Healthy Volunteers1
1CompletedTreatmentCastration Resistant Prostate Cancer (CRPC) / Castration-Resistant Prostate Cancer (CRPC) / Pharmacokinetics of MDV31001
1CompletedTreatmentCrohn's Disease (CD)1
1CompletedTreatmentCystic Fibrosis (CF)1
1CompletedTreatmentHealthy Volunteers8
1CompletedTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD)1
1CompletedTreatmentObese1
1CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
1CompletedTreatmentType 1 Diabetes Mellitus1
1CompletedTreatmentType 2 Diabetes Mellitus3
1Not Yet RecruitingHealth Services ResearchType 2 Diabetes Mellitus1
1RecruitingTreatmentInsulin Resistance / Rheumatoid Arthritis1
1TerminatedTreatmentOpioid-Related Disorders1
1Unknown StatusTreatmentMalignant Neoplasm of Pancreas1
1WithdrawnNot AvailableType 2 Diabetes Mellitus1
1, 2Active Not RecruitingPreventionSystemic Lupus Erythematosus (SLE)1
1, 2CompletedTreatmentAlcohol Use Disorder (AUD) / Cocaine Use Disorders1
1, 2CompletedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
1, 2CompletedTreatmentSevere Sepsis / Shock, Septic1
1, 2CompletedTreatmentType 2 Diabetes Mellitus1
1, 2Not Yet RecruitingTreatmentDiabetes / Hyperglycemia / Stroke, Acute1
1, 2RecruitingTreatmentAlcohol Use Disorder (AUD)1
1, 2RecruitingTreatmentDisseminated Sclerosis1
1, 2RecruitingTreatmentLeukemia, Myeloid, Chronic-Phase1
1, 2TerminatedBasic ScienceHeroin Dependence / Nicotine Dependence1
1, 2TerminatedTreatmentChronic Granulomatous Disease (CGD)1
1, 2Unknown StatusTreatmentAdvanced Melanoma1
1, 2Unknown StatusTreatmentMultiple Myeloma (MM)1
2Active Not RecruitingOtherChronic Myeloid Leukemia (CML)1
2Active Not RecruitingTreatmentPolycystic Kidney Diseases1
2CompletedDiagnosticDiabetes / Healthy Volunteers / Platelet Function1
2CompletedPreventionEndobronchial Dysplasia / Lung Cancers1
2CompletedPreventionHead and Neck Carcinoma / Oral Leukoplakia1
2CompletedPreventionMild Cognitive Impairment (MCI)1
2CompletedTreatmentAdrenomyeloneuropathy / X-Linked Adrenoleukodystrophy1
2CompletedTreatmentAirway Inflammation / Airway Obstruction / Severe, Refractory Asthma1
2CompletedTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentAsthma1
2CompletedTreatmentAutism Spectrum Conditions/Disorders1
2CompletedTreatmentBMI >30 kg/m21
2CompletedTreatmentCancer of the Pancreas1
2CompletedTreatmentCardiac Allograft Vasculopathy / Cardiac Transplant1
2CompletedTreatmentCardiovascular Heart Disease1
2CompletedTreatmentCerebral Hemorrhage1
2CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
2CompletedTreatmentCoronary Artery Disease / Oxidative Stress / Type 2 Diabetes Mellitus1
2CompletedTreatmentDiabetes Mellitus3
2CompletedTreatmentDiabetes Mellitus / Glucose Metabolism Disorders / Type 2 Diabetes Mellitus1
2CompletedTreatmentDiabetes Mellitus / Insulin Resistance1
2CompletedTreatmentESRD1
2CompletedTreatmentFatty Liver / Nonalcoholic Steatohepatitis1
2CompletedTreatmentHIV Lipodystrophy1
2CompletedTreatmentHIV-1 and Hepatitis C Co-Infection1
2CompletedTreatmentHepatic Steatosis / Human Immunodeficiency Virus (HIV) Infections / Insulin Resistance1
2CompletedTreatmentHepatitis1
2CompletedTreatmentHigh Blood Pressure (Hypertension) / Inflammatory Reaction1
2CompletedTreatmentImpaired Glucose Tolerance / Transplantation, Kidney1
2CompletedTreatmentInsulin Resistance / Metabolic Syndromes / Type 2 Diabetes Mellitus1
2CompletedTreatmentInsulin Resistance / Normal or Mildly Abnormal Stool Fat Levels / Normal Stool Fat Levels / Pancreatitis, Chronic1
2CompletedTreatmentLeukemia, Myeloid, Chronic-Phase1
2CompletedTreatmentMajor Depressive Disorder (MDD) / Metabolic Syndromes1
2CompletedTreatmentNonalcoholic Fatty Liver Disease1
2CompletedTreatmentOpioid Abuse1
2CompletedTreatmentParkinson's Disease (PD)1
2CompletedTreatmentPolycystic Ovarian Syndrome1
2CompletedTreatmentProstate Cancer1
2CompletedTreatmentPsoriasis1
2CompletedTreatmentThyroid Cancers That Contain the PAX8-PPARgamma Fusion Gene1
2CompletedTreatmentType 2 Diabetes Mellitus16
2Enrolling by InvitationPreventionSquamous Cell Carcinoma of the Skin1
2Not Yet RecruitingTreatmentLeukemia, Myelogenous, Chronic, BCR-ABL Positive1
2RecruitingTreatmentAlcohol Dependence1
2RecruitingTreatmentChronic Myeloid Leukemia (CML)1
2RecruitingTreatmentDiabetes Mellitus Type 2 With Hyperglycemia1
2RecruitingTreatmentHepatitis1
2RecruitingTreatmentLeukemia Acute Myeloid Leukemia (AML)1
2RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC) / Non-squamous Cell Lung Cancer / Squamous Cell Carcinoma of Lung1
2TerminatedNot AvailableType 2 Diabetes Mellitus1
2TerminatedPreventionNeoplasms, Oropharyngeal / Oral Cavity Neoplasm / Stage 0 Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage 0 Oropharyngeal Squamous Cell Carcinoma AJCC v6 and v7 / Stage I Oral Cavity Squamous Cell Carcinoma / Stage I Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage I Oropharyngeal Squamous Cell Carcinoma / Stage I Oropharyngeal Squamous Cell Carcinoma AJCC v6 and v7 / Stage II Oral Cavity Squamous Cell Carcinoma / Stage II Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage II Oropharyngeal Squamous Cell Carcinoma / Stage II Oropharyngeal Squamous Cell Carcinoma AJCC v6 and v7 / Stage III Oral Cavity Squamous Cell Carcinoma / Stage III Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage III Oropharyngeal Squamous Cell Carcinoma / Stage III Oropharyngeal Squamous Cell Carcinoma AJCC v7 / Stage IV Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage IV Oropharyngeal Squamous Cell Carcinoma AJCC v7 / Stage IVA Oral Cavity Squamous Cell Carcinoma / Stage IVA Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage IVA Oropharyngeal Squamous Cell Carcinoma / Stage IVA Oropharyngeal Squamous Cell Carcinoma AJCC v7 / Stage IVB Oral Cavity Squamous Cell Carcinoma / Stage IVB Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage IVB Oropharyngeal Squamous Cell Carcinoma / Stage IVB Oropharyngeal Squamous Cell Carcinoma AJCC v7 / Stage IVC Oral Cavity Squamous Cell Carcinoma / Stage IVC Oral Cavity Squamous Cell Carcinoma AJCC v6 and v7 / Stage IVC Oropharyngeal Squamous Cell Carcinoma / Stage IVC Oropharyngeal Squamous Cell Carcinoma AJCC v71
2TerminatedTreatmentAlcohol Dependence / Alcohol Drinking / Alcohol-Related Disorders / Stress1
2TerminatedTreatmentAmyotrophic Lateral Sclerosis (ALS)1
2TerminatedTreatmentAsthma / BMI >30 kg/m21
2TerminatedTreatmentChronic Kidney Disease (CKD)1
2TerminatedTreatmentChronic Myelogenous Leukemia, BCR-ABL1 Positive / Recurrent Chronic Myelogenous Leukemia, BCR-ABL1 Positive1
2TerminatedTreatmentDiabetes Mellitus1
2TerminatedTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2TerminatedTreatmentNonalcoholic Steatohapatitis1
2TerminatedTreatmentOral Leukoplakia1
2TerminatedTreatmentStage IA Non-Small Cell Lung Carcinoma / Stage IB Non-Small Cell Lung Carcinoma / Stage IIA Non-Small Cell Lung Carcinoma / Stage IIB Non-Small Cell Lung Carcinoma / Stage IIIA Non-Small Cell Lung Cancer1
2TerminatedTreatmentStroke1
2TerminatedTreatmentType 2 Diabetes Mellitus2
2WithdrawnOtherHepatitis C Viral Infection1
2WithdrawnTreatmentAirway Hyperactivity / Airway Inflammation / Airway Obstruction / Asthma1
2WithdrawnTreatmentPressure Ulcers / Spinal Cord Injuries (SCI)1
2, 3CompletedTreatmentArterial Occlusive Diseases / Insulin Resistance / Intermittent Claudication1
2, 3CompletedTreatmentCoronary Artery Disease / Type 2 Diabetes Mellitus1
2, 3CompletedTreatmentMajor Depressive Disorder (MDD)1
2, 3CompletedTreatmentType 2 Diabetes Mellitus4
2, 3Not Yet RecruitingOtherInsulin Sensitivity1
2, 3Not Yet RecruitingTreatmentNewly Diagnosed Type 2 Diabetes1
2, 3WithdrawnDiagnosticEndometriosis1
3CompletedBasic ScienceType 2 Diabetes Mellitus1
3CompletedPreventionAtherosclerosis / Cardiovascular Heart Disease / Coronary Heart Disease (CHD) / Diabetes Mellitus / High Blood Pressure (Hypertension) / High Cholesterol / Type 2 Diabetes Mellitus1
3CompletedPreventionImpaired Glucose Tolerance / Type 2 Diabetes Mellitus1
3CompletedTreatmentDiabetes1
3CompletedTreatmentDiabetes Mellitus12
3CompletedTreatmentDiabetes Mellitus / Dyslipidemia1
3CompletedTreatmentDiabetes Mellitus / Proteinuria / Transplantation, Kidney1
3CompletedTreatmentDiabetes / Myocardial Infarction / Stroke1
3CompletedTreatmentDiabetes / Type 2 Diabetes Mellitus2
3CompletedTreatmentFriedreich's Ataxia1
3CompletedTreatmentHigh Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
3CompletedTreatmentLiver Diseases1
3CompletedTreatmentRheumatoid Arthritis1
3CompletedTreatmentType 2 Diabetes Mellitus40
3Not Yet RecruitingHealth Services ResearchRisk Reduction1
3TerminatedTreatmentChronic Hepatitis C Virus (HCV) Infection / Insulin Resistance1
3TerminatedTreatmentDiabetes Mellitus1
3TerminatedTreatmentDiabetes / Type 2 Diabetes Mellitus1
3TerminatedTreatmentHIV-Associated Lipodystrophy Syndrome / Human Immunodeficiency Virus (HIV) Infections1
3TerminatedTreatmentMild Cognitive Impairment Due to Alzheimer's Disease2
3TerminatedTreatmentType 2 Diabetes Mellitus4
3Unknown StatusTreatmentCoronary Artery Atherosclerosis / Coronary Artery Restenosis / Diabetes1
3Unknown StatusTreatmentFatty Liver1
3Unknown StatusTreatmentMetabolic Syndromes1
4Active Not RecruitingTreatmentCardiovascular Heart Disease / Type 2 Diabetes Mellitus1
4Active Not RecruitingTreatmentDiabetes1
4Active Not RecruitingTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD) / Type2 Diabetes Mellitus1
4CompletedNot AvailableDiabetes Mellitus1
4CompletedNot AvailableDiabetic Nephropathies / Dyslipidemia / High Blood Pressure (Hypertension) / Type 2 Diabetes Mellitus1
4CompletedNot AvailableType 2 Diabetes Mellitus1
4CompletedBasic ScienceDiabetes1
4CompletedBasic ScienceDiabetes / Glucose Metabolism Disorders1
4CompletedBasic ScienceInsulin Resistance / Metabolic Syndromes / Pre-Diabetic1
4CompletedBasic ScienceType 2 Diabetes Mellitus2
4CompletedPreventionAdverse Effects / Coronary Artery Atherosclerosis / Insulin resistance syndrome1
4CompletedPreventionAngina Pectoris / Coronary Artery Disease / Percutaneous Coronary Intervention (PCI) / Type 2 Diabetes Mellitus1
4CompletedPreventionDiabetes1
4CompletedTreatmentAscites / Liver Cirrhosis / Portal Hypertension1
4CompletedTreatmentAtaxia Telangiectasia (AT) / Ataxia-Telangiectasia1
4CompletedTreatmentAtherosclerosis / Coronary Artery Disease1
4CompletedTreatmentBMI >30 kg/m2 / Impaired Glucose Tolerance / Metabolic Syndromes1
4CompletedTreatmentBMI >30 kg/m2 / Overweight With Indications for Weight Loss1
4CompletedTreatmentBone Metabolism1
4CompletedTreatmentCardiovascular Heart Disease / Type 2 Diabetes Mellitus1
4CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection2
4CompletedTreatmentCognitive Impairments / Diabetes / Insulin Resistance / Schizophrenia1
4CompletedTreatmentCoronary Artery Stenosis / Diabetes Mellitus1
4CompletedTreatmentCoronary Heart Disease (CHD) / Type 2 Diabetes Mellitus1
4CompletedTreatmentDepression, Bipolar / Insulin Resistance / Metabolic Syndromes1
4CompletedTreatmentDiabetes Mellitus5
4CompletedTreatmentDiabetes Mellitus / Livers1
4CompletedTreatmentDiabetes / High Blood Pressure (Hypertension)1
4CompletedTreatmentDiabetic Stable Angina / Diabetic Unstable Angina1
4CompletedTreatmentEnd Stage Renal Disease (ESRD) / End-Stage Renal Disease (ESRD)1
4CompletedTreatmentEndothelial Function / LVM / Type 2 Diabetic Patients With IHD1
4CompletedTreatmentHealthy Volunteers / Impaired Glucose Tolerance / Type 2 Diabetes Mellitus1
4CompletedTreatmentHepatitis C Viral Infection1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Insulin Resistance1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedTreatmentInflammatory Reaction1
4CompletedTreatmentInsulin Resistance / Polycystic Ovaries Syndrome1
4CompletedTreatmentInsulin Resistance / Type 2 Diabetes Mellitus2
4CompletedTreatmentMetabolic Syndromes2
4CompletedTreatmentNonalcoholic Fatty Liver Disease / Nonalcoholic Steatohepatitis / Type 2 Diabetes Mellitus1
4CompletedTreatmentNonalcoholic Steatohepatitis2
4CompletedTreatmentPolycystic Ovaries Syndrome1
4CompletedTreatmentSecondary Drug Failure / Type 2 Diabetes Mellitus1
4CompletedTreatmentSystemic Lupus Erythematosus (SLE)1
4CompletedTreatmentType 2 Diabetes Mellitus16
4CompletedTreatmentType 2 Diabetes Mellitus / Vascular Diseases1
4CompletedTreatmentType 2 Diabetes With Non-alcoholic Fatty Liver (NAFLD)1
4CompletedTreatmentType2 Diabetes1
4Enrolling by InvitationTreatmentNon-Alcoholic Fatty Liver Disease (NAFLD) / Type2 Diabetes1
4Enrolling by InvitationTreatmentType 2 Diabetes Mellitus1
4Not Yet RecruitingTreatmentDiabetes Mellitus / Osteoporosis1
4Not Yet RecruitingTreatmentNAFLD - Nonalcoholic Fatty Liver Disease / Type2 Diabetes1
4Not Yet RecruitingTreatmentNon-Alcoholic Steatohepatitis / Type2 Diabetes1
4Not Yet RecruitingTreatmentType2 Diabetes Mellitus1
4RecruitingBasic ScienceChronic Kidney Disease (CKD)1
4RecruitingTreatmentType 1 Diabetes Mellitus1
4RecruitingTreatmentType 2 Diabetes Mellitus6
4TerminatedPreventionDiabetes Mellitus / Myocardial Infarction1
4TerminatedTreatmentAsthma1
4TerminatedTreatmentBipolar Disorder (BD) / Insulin Resistance1
4TerminatedTreatmentFatty Liver / Hepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections / Liver Diseases / Steatosis1
4TerminatedTreatmentNonalcoholic Fatty Liver / Type 2 Diabetes Mellitus1
4TerminatedTreatmentOSAS (Obstructive Sleep Apneas Syndrome) / Polycystic Ovaries Syndrome1
4TerminatedTreatmentPulmonary Hypertension (PH)1
4TerminatedTreatmentType 2 Diabetes Mellitus3
4Unknown StatusBasic ScienceType 2 Diabetes Mellitus1
4Unknown StatusTreatmentChronic Hepatitis C Virus (HCV) Infection1
4Unknown StatusTreatmentCoronary Artery Atherosclerosis / Coronary Heart Disease (CHD) / Inflammatory Reaction1
4Unknown StatusTreatmentDiabetes1
4Unknown StatusTreatmentDiabetes Mellitus / Oxidative Stress1
4Unknown StatusTreatmentESRD1
4Unknown StatusTreatmentInsulin Resistance / Major Depressive Disorder (MDD)1
4Unknown StatusTreatmentType 2 Diabetes Mellitus2
4WithdrawnHealth Services ResearchType 2 Diabetes Mellitus1
4WithdrawnTreatmentBMI >30 kg/m2 / Insulin Resistance1
4WithdrawnTreatmentGlucose Metabolism Disorders1
4WithdrawnTreatmentType 2 Diabetes Mellitus1
Not AvailableCompletedNot AvailableAdipocytes / Adiponectin / Bone Density / Mesenchymal Stem Cells / Osteoblast / Osteocalcin1
Not AvailableCompletedNot AvailableCancer, Bladder / Diabetes1
Not AvailableCompletedNot AvailableChronic Hepatitis C Virus (HCV) Infection1
Not AvailableCompletedNot AvailableCongenital Adrenal Hyperplasia (CAH)1
Not AvailableCompletedNot AvailableDiabetes Mellitus, Type 2, Cancer1
Not AvailableCompletedNot AvailableDiabetic Ketoacidosis / Ketosis Prone Diabetes / Severe Hyperglycemia1
Not AvailableCompletedNot AvailableType 2 Diabetes Mellitus12
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Insulin Resistance1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Metabolic Syndromes1
Not AvailableCompletedBasic ScienceBMI >30 kg/m2 / Sarcopenia1
Not AvailableCompletedBasic ScienceMetabolic Syndromes / Prediabetic State1
Not AvailableCompletedBasic SciencePolycystic Ovaries Syndrome1
Not AvailableCompletedBasic ScienceRheumatoid Arthritis1
Not AvailableCompletedBasic ScienceType 2 Diabetes Mellitus5
Not AvailableCompletedDiagnosticCardiovascular Heart Disease / HIV Lipodystrophy / Human Immunodeficiency Virus (HIV) Infections / Insulin Resistance / The Metabolic Syndrome1
Not AvailableCompletedOtherAnti Inflammatory Non-Steroidal / Cystic Fibrosis (CF) / Neutrophils1
Not AvailableCompletedOtherHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedPreventionAtherosclerosis / Insulin Resistance / Transplantation, Kidney1
Not AvailableCompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / BMI >30 kg/m2 / Cardiovascular Heart Disease / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentAtherosclerosis / Impaired Glucose Tolerance / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentBMI >30 kg/m2 / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedTreatmentDiabetes / Endstage Renal Disease1
Not AvailableCompletedTreatmentDiabetic Nephropathies / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentEnd Stage Renal Disease (ESRD) / Hemodialysis Treatment1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentHuman Growth Hormone Deficiency1
Not AvailableCompletedTreatmentHypertriglyceridemias / Inflammatory Reaction / Insulin Resistance / Peritoneal dialysis therapy / Pioglitazone1
Not AvailableCompletedTreatmentNewly Diagnosed / Type 2 Diabetes Mellitus1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus3
Not AvailableRecruitingNot AvailableCancer, Bladder1
Not AvailableRecruitingBasic ScienceUric Acid Kidney Stone Disease1
Not AvailableRecruitingOtherType 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentImpaired Fasting Glucose (IFG) / Impaired Glucose Tolerance / Type 2 Diabetes Mellitus1
Not AvailableRecruitingTreatmentType 2 Diabetes Mellitus1
Not AvailableTerminatedNot AvailableDiabetes / Hypogonadism / Inflammatory Reaction / Metabolic Syndromes1
Not AvailableTerminatedNot AvailableType 2 Diabetes Mellitus1
Not AvailableTerminatedBasic ScienceFatty Liver1
Not AvailableTerminatedHealth Services ResearchPolycystic Ovaries Syndrome1
Not AvailableTerminatedPreventionPrediabetic State1
Not AvailableTerminatedTreatmentChronic Kidney Disease (CKD)1
Not AvailableTerminatedTreatmentType 2 Diabetes Mellitus1
Not AvailableUnknown StatusNot AvailableInsulin Sensitivity / OSAS (Obstructive Sleep Apneas Syndrome)1
Not AvailableUnknown StatusBasic ScienceBMI >30 kg/m2 / Cardiovascular Heart Disease / Type 2 Diabetes Mellitus1
Not AvailableUnknown StatusTreatmentMetabolic Parameters and Liver Histology1
Not AvailableUnknown StatusTreatmentTo Evaluate the Effect of Pioglitazone on Glucose Metabolism of Fat Tissue by Using FDG-PET/CT Imaging1
Not AvailableUnknown StatusTreatmentType 2 Diabetes Mellitus1
Not AvailableWithdrawnTreatmentAtopic Dermatitis (AD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • DispenseXpress Inc.
  • Diversified Healthcare Services Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmacy Service Center
  • Physician Partners Ltd.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Quality Care
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Southwood Pharmaceuticals
  • Takeda Pharmaceutical Co. Ltd.
  • Vangard Labs Inc.
Dosage forms
FormRouteStrength
Tablet, film coated, extended releaseOral
TabletOcclusive dressing technique15 mg/1
TabletOral15 mg/1
TabletOral30 mg/1
TabletOral45 mg/1
TabletOral15 mg
TabletOral30 mg
TabletOral45 mg
Tablet, film coatedOral
TabletOral
TabletOral
Prices
Unit descriptionCostUnit
Actos 30 mg tablet12.48USD tablet
Actos 45 mg tablet11.22USD tablet
Actos 15 mg tablet6.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4687777No1987-08-182011-01-17Us
CA2179584No2007-04-242016-06-20Canada
CA2531834No2006-12-052016-06-20Canada
US6150383No2000-11-212016-06-19Us
US6211205No2001-04-032016-06-19Us
US6303640No2001-10-162016-08-09Us
US6329404No2001-12-112016-06-19Us
US8071130No2011-12-062028-06-08Us
US7538125No2009-05-262016-06-19Us
US7700128No2010-04-202027-01-30Us
US5965584No1999-10-122016-06-19Us
US6166042No2000-12-262016-06-19Us
US6166043No2000-12-262016-06-19Us
US6172090No2001-01-092016-06-19Us
US6790459No2004-09-142021-03-17Us
US7919116No2011-04-052018-03-20Us
US8475841No2013-07-022018-03-20Us
US6099859No2000-08-082018-03-20Us
US6866866No2005-03-152021-03-17Us
US7785627No2010-08-312026-07-31Us
US7959946No2011-06-142026-07-31Us
US8470368No2013-06-252023-09-19Us
US8668931No2014-03-112023-09-19Us
US9060941No2015-06-232023-09-19Us
US6495162No2002-12-172018-03-20Us
US6150384No2000-11-212016-06-19Us
US6271243No2001-08-072016-06-19Us
US9101660No2015-08-112027-01-22Us
US6303661No2001-10-162017-04-24Us
US6890898No2005-05-102019-02-02Us
US7078381No2006-07-182019-02-02Us
US7459428No2008-12-022019-02-02Us
US7807689No2010-10-052028-06-27Us
US8173663No2012-05-082025-03-15Us
US8288539No2012-10-162025-03-15Us
US8637079No2014-01-282029-06-04Us
US9320714No2016-04-262029-02-03Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)193-194CAl-Majed, A. et. al.
water solubilityPractically insolubleFDA Label
pKa5.19Al-Majed, A. et. al.
Predicted Properties
PropertyValueSource
Water Solubility0.00442 mg/mLALOGPS
logP3.17ALOGPS
logP3.33ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)6.66ChemAxon
pKa (Strongest Basic)5.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area68.29 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity97.39 m3·mol-1ChemAxon
Polarizability37.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9952
Blood Brain Barrier+0.8753
Caco-2 permeable-0.5659
P-glycoprotein substrateNon-substrate0.6358
P-glycoprotein inhibitor INon-inhibitor0.5708
P-glycoprotein inhibitor IINon-inhibitor0.9673
Renal organic cation transporterNon-inhibitor0.6018
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.5267
CYP450 1A2 substrateInhibitor0.8384
CYP450 2C9 inhibitorInhibitor0.6353
CYP450 2D6 inhibitorNon-inhibitor0.8085
CYP450 2C19 inhibitorInhibitor0.6967
CYP450 3A4 inhibitorNon-inhibitor0.6035
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8864
Ames testNon AMES toxic0.7303
CarcinogenicityNon-carcinogens0.9171
BiodegradationNot ready biodegradable0.7884
Rat acute toxicity2.0115 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9341
hERG inhibition (predictor II)Non-inhibitor0.8498
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0009000000-070cf69939743719671d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0bt9-0209000000-d9d34be41f49a9ffbdef
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-ef25b6f93ae4fcee23c3
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0udi-0900000000-3011f00e839bfc06d89d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0gba-0900000000-b0488e0d155d1587bbb5
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014j-0900000000-b32570ad6af58a4a6c72
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0a4i-0009000000-c67370f6cb2ad36cab3e
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a59-0908000000-aab2ee9addb1334a7064
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-0009000000-fd4bc4d9d4bb45e91295
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0a4i-0409000000-115c6889c4e9205b3028
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-a2e878da4d2f6a4bb717
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-031fa259cd3b26217dad
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lr-0900000000-e2cd3c294a2e53e1a17e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0159-1900000000-aacbd8dce006b5ef5938
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-1619000000-4b248e31af7f50e87108
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-053r-0906000000-a73152b364036b45dfeb

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenol ethers
Sub Class
Not Available
Direct Parent
Phenol ethers
Alternative Parents
Phenoxy compounds / Thiazolidinediones / Alkyl aryl ethers / Pyridines and derivatives / Heteroaromatic compounds / Dicarboximides / Thiocarbamic acid derivatives / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Phenoxy compound / Phenol ether / Alkyl aryl ether / Thiazolidinedione / Monocyclic benzene moiety / Pyridine / Dicarboximide / Heteroaromatic compound / Thiazolidine / Carbonic acid derivative
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, pyridines, thiazolidenediones (CHEBI:8228)

Targets

Kind
Protein
Organism
Humans
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...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Sugii S, Olson P, Sears DD, Saberi M, Atkins AR, Barish GD, Hong SH, Castro GL, Yin YQ, Nelson MC, Hsiao G, Greaves DR, Downes M, Yu RT, Olefsky JM, Evans RM: PPARgamma activation in adipocytes is sufficient for systemic insulin sensitization. Proc Natl Acad Sci U S A. 2009 Dec 29;106(52):22504-9. doi: 10.1073/pnas.0912487106. Epub 2009 Dec 16. [PubMed:20018750]
  2. Miyazaki Y, Mahankali A, Wajcberg E, Bajaj M, Mandarino LJ, DeFronzo RA: Effect of pioglitazone on circulating adipocytokine levels and insulin sensitivity in type 2 diabetic patients. J Clin Endocrinol Metab. 2004 Sep;89(9):4312-9. [PubMed:15356026]
  3. Spiegelman BM: PPAR-gamma: adipogenic regulator and thiazolidinedione receptor. Diabetes. 1998 Apr;47(4):507-14. [PubMed:9568680]
  4. Willson TM, Cobb JE, Cowan DJ, Wiethe RW, Correa ID, Prakash SR, Beck KD, Moore LB, Kliewer SA, Lehmann JM: The structure-activity relationship between peroxisome proliferator-activated receptor gamma agonism and the antihyperglycemic activity of thiazolidinediones. J Med Chem. 1996 Feb 2;39(3):665-8. [PubMed:8576907]
  5. FDA Approved Drug Products: Actos (pioglitazone) oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Binda C, Aldeco M, Geldenhuys WJ, Tortorici M, Mattevi A, Edmondson DE: Molecular Insights into Human Monoamine Oxidase B Inhibition by the Glitazone Anti-Diabetes Drugs. ACS Med Chem Lett. 2011 Oct 15;3(1):39-42. [PubMed:22282722]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Muschler E, Lal J, Jetter A, Rattay A, Zanger U, Zadoyan G, Fuhr U, Kirchheiner J: The role of human CYP2C8 and CYP2C9 variants in pioglitazone metabolism in vitro. Basic Clin Pharmacol Toxicol. 2009 Dec;105(6):374-9. doi: 10.1111/j.1742-7843.2009.00457.x. Epub 2009 Jul 15. [PubMed:19614891]
  2. Jaakkola T, Laitila J, Neuvonen PJ, Backman JT: Pioglitazone is metabolised by CYP2C8 and CYP3A4 in vitro: potential for interactions with CYP2C8 inhibitors. Basic Clin Pharmacol Toxicol. 2006 Jul;99(1):44-51. doi: 10.1111/j.1742-7843.2006.pto_437.x. [PubMed:16867170]
  3. Sahi J, Black CB, Hamilton GA, Zheng X, Jolley S, Rose KA, Gilbert D, LeCluyse EL, Sinz MW: Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46. [PubMed:12642470]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  5. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
Curator comments
One study suggests that another thiazolidinedione, troglitazone, induces CYP3A4. Pioglitazone is a member of the same drug class, and likely has the same effect.
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Jaakkola T, Laitila J, Neuvonen PJ, Backman JT: Pioglitazone is metabolised by CYP2C8 and CYP3A4 in vitro: potential for interactions with CYP2C8 inhibitors. Basic Clin Pharmacol Toxicol. 2006 Jul;99(1):44-51. doi: 10.1111/j.1742-7843.2006.pto_437.x. [PubMed:16867170]
  2. Sahi J, Black CB, Hamilton GA, Zheng X, Jolley S, Rose KA, Gilbert D, LeCluyse EL, Sinz MW: Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition. Drug Metab Dispos. 2003 Apr;31(4):439-46. [PubMed:12642470]
  3. Nowak SN, Edwards DJ, Clarke A, Anderson GD, Jaber LA: Pioglitazone: effect on CYP3A4 activity. J Clin Pharmacol. 2002 Dec;42(12):1299-302. [PubMed:12463723]
  4. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. FDA Approved Drug Products: Actos (pioglitazone) oral tablets [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. FDA Approved Drug Products: Actos (pioglitazone) oral tablets [Link]

Transporters

Kind
Protein
Organism
Humans
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 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 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]
Kind
Protein
Organism
Humans
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, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
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]

Drug created on June 13, 2005 07:24 / Updated on April 03, 2020 10:31

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