NAV

Lobeglitazone

Identification

Generic Name
Lobeglitazone
DrugBank Accession Number
DB09198
Background

Lobeglitazone is an antidiabetic medication from the thiazolidinedione class of drugs. It primarily functions as an insulin sensitizer by binding and activating Peroxisome Proliferator-Activated Receptors (PPAR) gamma within fat cells. By activating PPAR-gamma and promoting the binding of insulin at fat cells, lobeglitazone thereby has been shown to reduce blood sugar levels, lower hemoglobain A1C (HbA1C) levels, and improve lipid and liver profiles 1. Unlike Pioglitazone, which is a dual PPAR agonist at PPAR-alpha and PPAR-gamma, Lobeglitazone is a pure PPAR-alpha agonist.

Lobeglitazone was approved by the Ministry of Food and Drug Safety (South Korea) in 2013, and is being monitored by postmarketing surveillance until 2019. Lobeglitazone is not approved for use by either the Food and Drug Administration (USA), Health Canada, or by the European Medicines Agency for use in the management of diabetes.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 480.54
Monoisotopic: 480.146741063
Chemical Formula
C24H24N4O5S
Synonyms
  • Lobeglitazone
External IDs
  • CKD 501
  • CKD-501
  • CKD501
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Pharmacology

Indication

Lobeglitazone was approved by the Ministry of Food and Drug Safety (South Korea) in 2013, and is being monitored by postmarketing surveillance until 2019. Lobeglitazone is not approved for use by either the Food and Drug Administration (USA), Health Canada, or by the European Medicines Agency for use in the management of diabetes.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Lobeglitazone acts as an insulin sensitizer by binding and activating Peroxisome Proliferator-Activated Receptors (PPAR) gamma within fat cells. By promoting the binding of insulin at fat cells, lobeglitazone has been shown to reduce blood sugar levels, lower hemoglobain A1C (HbA1C) levels, and improve lipid and liver profiles 1. Unlike Pioglitazone, which is a dual PPAR agonist at PPAR-alpha and PPAR-gamma, Lobeglitazone is a pure PPAR-alpha agonist.

TargetActionsOrganism
APeroxisome proliferator-activated receptor gamma
activator
Humans
Absorption

In rat studies, the AUC for the doses 0.5, 1, and 2 mg/kg, AUC values were determined to be 459, 514, and 481 ug min/mL respectively. Absoprtion occurs rapidly after administration, with Tmax of 67.5 and 48.8 min and a Cmax of 0.962 and 0.4.94 ug/mL following doses of 0.5 and 2 mg/kg, respectively. Absolute bioavailability after oral administration was nearly complete and apparently not affected by the dosage; 92.1% following a 0.5 mg/kg dose and 99.0% following a 2 mg/kg dose. Furthermore, the extent of LB remaining in the GI tract at 24 h was found to be negligible, with values less than 0.2% of the oral dose, suggesting that the intestinal absorption is complete in rats at the dose range studied 2.

Volume of distribution

The steady state volume of distribution (Vss) of lobeglitazone was found to be 189–276 mL/kg. Vss was not found to vary statistically with the dose, suggesting that lobeglitazone follows linear kinetics 2.

Protein binding

Lobeglitazone was found to bind extensively to plasma proteins (i.e., up to 99.9%) with no appreciable concentration dependency on the unbound fraction 2.

Metabolism

Rat studies with lobeglitazone have suggested that it is primarily metabolized by cytochrome P450 (CYP) isozymes 2, however the exact enzymes involved in its metabolism have yet to be elucidated. The structure of Lobeglitazone's five major metabolites have been characterized along with their pharmacokinetic parameters, and can be seen in the metabolism section below. In rat studies, demethylation and hydroxylation appear to be the primary metabolic pathways. The most abundant metabolite found in these studies was confirmed in vivo as M1, a demethylated derivative of lobeglitazone; its rate of formation was found to be approximately 0.216 ∼ 0.252 mL/min/kg, representing approximately 9.76% of the total lobeglitazone elimination in vivo in rats 5.

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Route of elimination

It has been reported that the combined extent of the excretion of lobeglitazone to the bile, urine and intestine is low (less than 10% of total dose), suggesting that the major route of elimination for the drug involves its metabolism 2.

Half-life

Following an intravenous dosage of 1 mg/kg, the half life was found to be 110 min 2.

Clearance

In rat studies, systemic clearance was found to be between 1.95 and 2.19 mL/min/kg regardless of dosage 2.

Adverse Effects
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Toxicity

Lobeglitazone showed a similar adverse effect profile to pioglitazone, another thiazolidinedione medication from the same class. The most concerning side effects found were edema and weight gain, with no severe adverse effects. Notably, there were no observable changes to patients with heart failure, which is a concern associated with other medications of the same class 3.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
Integrate drug-drug
interactions in your software
AbametapirThe serum concentration of Lobeglitazone can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Lobeglitazone can be increased when combined with Abatacept.
AbirateroneThe metabolism of Lobeglitazone can be decreased when combined with Abiraterone.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Lobeglitazone.
AcarboseThe risk or severity of hypoglycemia can be increased when Acarbose is combined with Lobeglitazone.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
lobeglitazone sulfate95C712E83PNot AvailableNot applicable
International/Other Brands
Duvie (Chong Kun Dang)

Categories

ATC Codes
A10BG04 — LobeglitazoneA10BD26 — Metformin and lobeglitazone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Diarylethers
Alternative Parents
Phenoxy compounds / Methoxybenzenes / Anisoles / Dialkylarylamines / Thiazolidinediones / Alkyl aryl ethers / Aminopyrimidines and derivatives / Imidolactams / Heteroaromatic compounds / Dicarboximides
show 7 more
Substituents
Alkyl aryl ether / Aminopyrimidine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dialkylarylamine
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
MY89F08K5D
CAS number
607723-33-1
InChI Key
CHHXEZSCHQVSRE-UHFFFAOYSA-N
InChI
InChI=1S/C24H24N4O5S/c1-28(21-14-22(26-15-25-21)33-19-9-7-17(31-2)8-10-19)11-12-32-18-5-3-16(4-6-18)13-20-23(29)27-24(30)34-20/h3-10,14-15,20H,11-13H2,1-2H3,(H,27,29,30)
IUPAC Name
5-{[4-(2-{[6-(4-methoxyphenoxy)pyrimidin-4-yl](methyl)amino}ethoxy)phenyl]methyl}-1,3-thiazolidine-2,4-dione
SMILES
COC1=CC=C(OC2=NC=NC(=C2)N(C)CCOC2=CC=C(CC3SC(=O)NC3=O)C=C2)C=C1

References

Synthesis Reference

Kim BY, Ahn JB, Lee HW, Kang SK, Lee JH, Shin JS, Ahn SK, Hong CI, Yoon SS: Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione. Eur J Med Chem. 2004 May;39(5):433-47.

General References
  1. Lee YH, Kim JH, Kim SR, Jin HY, Rhee EJ, Cho YM, Lee BW: Lobeglitazone, a Novel Thiazolidinedione, Improves Non-Alcoholic Fatty Liver Disease in Type 2 Diabetes: Its Efficacy and Predictive Factors Related to Responsiveness. J Korean Med Sci. 2017 Jan;32(1):60-69. doi: 10.3346/jkms.2017.32.1.60. [Article]
  2. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]
  3. Jin SM, Park CY, Cho YM, Ku BJ, Ahn CW, Cha BS, Min KW, Sung YA, Baik SH, Lee KW, Yoon KH, Lee MK, Park SW: Lobeglitazone and pioglitazone as add-ons to metformin for patients with type 2 diabetes: a 24-week, multicentre, randomized, double-blind, parallel-group, active-controlled, phase III clinical trial with a 28-week extension. Diabetes Obes Metab. 2015 Jun;17(6):599-602. doi: 10.1111/dom.12435. Epub 2015 Feb 8. [Article]
  4. Kim BY, Ahn JB, Lee HW, Kang SK, Lee JH, Shin JS, Ahn SK, Hong CI, Yoon SS: Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione. Eur J Med Chem. 2004 May;39(5):433-47. [Article]
  5. Lee JH, Ahn SH, Maeng HJ, Lee W, Kim DD, Chung SJ: The identification of lobeglitazone metabolites in rat liver microsomes and the kinetics of the in vivo formation of the major metabolite M1 in rats. J Pharm Biomed Anal. 2015 Nov 10;115:375-82. doi: 10.1016/j.jpba.2015.07.040. Epub 2015 Jul 30. [Article]
PubChem Compound
9826451
PubChem Substance
310265106
ChemSpider
8002194
ChEBI
136052
ChEMBL
CHEMBL3585580
Wikipedia
Lobeglitazone

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedTreatmentFatty Liver, Non-alcoholic Fatty Liver Disease, NAFLD / Type 2 Diabetes Mellitus1
4CompletedTreatmentInadequate Glucose Control / Type 2 Diabetes Mellitus1
4CompletedTreatmentType 2 Diabetes Mellitus2
4RecruitingTreatmentType 2 Diabetes Mellitus2
3CompletedTreatmentType 2 Diabetes Mellitus3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0181 mg/mLALOGPS
logP3.84ALOGPS
logP4.31Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.61Chemaxon
pKa (Strongest Basic)3.96Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area102.88 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity129.63 m3·mol-1Chemaxon
Polarizability49.64 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0051900000-ffee035c5dfdeb3c25e5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fmi-0090200000-02fb1119ae0abd06715d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-08gi-0124900000-b849a6c9589c41ba993b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kmi-1329800000-4a3900af0279550b7bfe
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001u-0970600000-4b49926d92b5c0a8b38f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxr-3923300000-2a732dc35d78c8e0a6a3
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.29224
predicted
DeepCCS 1.0 (2019)
[M+H]+207.65245
predicted
DeepCCS 1.0 (2019)
[M+Na]+213.74336
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Peroxisome proliferator-activated receptor gamma
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
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. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]

Enzymes

Details1. Cytochrome P450 1A2
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]
  2. Jung JA, Lee SY, Kim TE, Kim JR, Kim C, Huh W, Ko JW: Lack of the effect of lobeglitazone, a peroxisome proliferator-activated receptor-gamma agonist, on the pharmacokinetics and pharmacodynamics of warfarin. Drug Des Devel Ther. 2015 Mar 2;9:737-43. doi: 10.2147/DDDT.S76591. eCollection 2015. [Article]
Details2. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]
Details3. Cytochrome P450 2C19
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
Curator comments
Data supporting this enzyme inhibition is limited.
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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]
Details4. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
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, Backman JT, Neuvonen M, Neuvonen PJ: Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14. doi: 10.1016/j.clpt.2004.12.266. [Article]
Details5. Cytochrome P450 2C8
Kind
Protein
Organism
Humans
Pharmacological action
No
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. Jaakkola T, Backman JT, Neuvonen M, Neuvonen PJ: Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14. doi: 10.1016/j.clpt.2004.12.266. [Article]
  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. [Article]

Transporters

Details1. Solute carrier organic anion transporter family member 1B1
Kind
Protein
Organism
Humans
Pharmacological action
No
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. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]
Details2. Solute carrier organic anion transporter family member 3A1
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as estrone-3-sulfate (PubMed:10873595). Mediates transport of prostaglandins (PG) E1 and E2, thyroxine (T4), deltorphin II, BQ-123 an...
Gene Name
SLCO3A1
Uniprot ID
Q9UIG8
Uniprot Name
Solute carrier organic anion transporter family member 3A1
Molecular Weight
76552.135 Da
References
  1. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]
Details3. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
No
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Lee JH, Noh CK, Yim CS, Jeong YS, Ahn SH, Lee W, Kim DD, Chung SJ: Kinetics of the Absorption, Distribution, Metabolism, and Excretion of Lobeglitazone, a Novel Activator of Peroxisome Proliferator-Activated Receptor Gamma in Rats. J Pharm Sci. 2015 Sep;104(9):3049-59. doi: 10.1002/jps.24378. Epub 2015 Feb 3. [Article]

Drug created at October 16, 2015 22:12 / Updated at February 21, 2021 18:52