NAV

Reglitazar

Identification

Generic Name
Reglitazar
DrugBank Accession Number
DB04971
Background

Reglitazar, an isoxazolidine-3,5-dione derivative, is being developed by Pfizer for the treatment of diabetes. It is the first non-thiazolidenedione to enter clinical trials.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 392.411
Monoisotopic: 392.137221752
Chemical Formula
C22H20N2O5
Synonyms
  • Reglitazar
  • Reglixane
External IDs
  • JTT 501
  • JTT 501beta
  • JTT-501
  • PNU 182716
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Pharmacology

Indication

For the treatment of diabetes mellitus type 1 and 2.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Reglixane shows a hypoglycemic effect and also a stronger triglyceride-lowering effect than the thiazolidine-2,4-diones. In preclinical studies, reglixane has been shown to prevent several diabetic complications, such as cataract, nephropathy, and neuropathy.

Mechanism of action

Reglixane is an agonist of peroxisome proliferator-activated receptor (PPAR) gamma and alpha.

TargetActionsOrganism
UPeroxisome proliferator-activated receptor alphaNot AvailableHumans
UPeroxisome proliferator-activated receptor gammaNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxazoles
Direct Parent
Phenyl-1,3-oxazoles
Alternative Parents
Phenoxy compounds / Phenol ethers / 2,4,5-trisubstituted oxazoles / Oxazolidinediones / Alkyl aryl ethers / 1,3-dicarbonyl compounds / Heteroaromatic compounds / Isoxazolidines / Carboxylic acid salts / Oxacyclic compounds
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Substituents
1,3-dicarbonyl compound / 2,4,5-trisubstituted 1,3-oxazole / Alkyl aryl ether / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid salt / Ether
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
P9UTN18JVV
CAS number
170861-63-9
InChI Key
QBQLYIISSRXYKL-UHFFFAOYSA-N
InChI
InChI=1S/C22H20N2O5/c1-14-19(23-21(28-14)16-5-3-2-4-6-16)11-12-27-17-9-7-15(8-10-17)13-18-20(25)24-29-22(18)26/h2-10,18H,11-13H2,1H3,(H,24,25)
IUPAC Name
4-({4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl}methyl)-1,2-oxazolidine-3,5-dione
SMILES
CC1=C(CCOC2=CC=C(CC3C(=O)NOC3=O)C=C2)N=C(O1)C1=CC=CC=C1

References

General References
Not Available
PubChem Substance
347909866
ChemSpider
135728
ChEMBL
CHEMBL293526

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.0244 mg/mLALOGPS
logP3.85ALOGPS
logP3.4Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.65Chemaxon
pKa (Strongest Basic)0.93Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area90.66 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity114.57 m3·mol-1Chemaxon
Polarizability41.32 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
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/MSsplash10-0006-0009000000-1d7e11b72f4cfce6cd71
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0229000000-8b63cba1315f8c48e0e1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-1493000000-8f8dd2368dfb0b6a51f9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bta-0946000000-527f57b2a4c7d9276bcb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9833000000-a1822a284cfd81c3033d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06ur-4911000000-48065af0a440589d33b5
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]-188.5835
predicted
DeepCCS 1.0 (2019)
[M+H]+190.94148
predicted
DeepCCS 1.0 (2019)
[M+Na]+198.45
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peroxisome proliferator-activated receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
Details2. Peroxisome proliferator-activated receptor gamma
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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

Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51