Ragaglitazar

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Ragaglitazar
DrugBank Accession Number
DB06533
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
Weight
Average: 419.477
Monoisotopic: 419.173272909
Chemical Formula
C25H25NO5
Synonyms
  • Ragaglitazar
External IDs
  • NN 622

Pharmacology

Indication

Investigated for use/treatment in diabetes mellitus type 2.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-substituted phenoxazines. These are phenoxyazines where the nitrogen atom is linked to an atom other than the hydrogen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzoxazines
Sub Class
Phenoxazines
Direct Parent
N-substituted phenoxazines
Alternative Parents
Alkyldiarylamines / Phenylpropanoic acids / Diarylethers / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Amino acids / Oxacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers
show 6 more
Substituents
3-phenylpropanoic-acid / Alkyl aryl ether / Alkyldiarylamine / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Q5ELR5A7Y5
CAS number
222834-30-2
InChI Key
WMUIIGVAWPWQAW-XMMPIXPASA-N
InChI
InChI=1S/C25H25NO5/c1-2-29-24(25(27)28)17-18-11-13-19(14-12-18)30-16-15-26-20-7-3-5-9-22(20)31-23-10-6-4-8-21(23)26/h3-14,24H,2,15-17H2,1H3,(H,27,28)/t24-/m1/s1
IUPAC Name
(2R)-2-ethoxy-3-{4-[2-(10H-phenoxazin-10-yl)ethoxy]phenyl}propanoic acid
SMILES
CCO[C@H](CC1=CC=C(OCCN2C3=CC=CC=C3OC3=C2C=CC=C3)C=C1)C(O)=O

References

General References
  1. Ye JM, Iglesias MA, Watson DG, Ellis B, Wood L, Jensen PB, Sorensen RV, Larsen PJ, Cooney GJ, Wassermann K, Kraegen EW: PPARalpha /gamma ragaglitazar eliminates fatty liver and enhances insulin action in fat-fed rats in the absence of hepatomegaly. Am J Physiol Endocrinol Metab. 2003 Mar;284(3):E531-40. [Article]
ChemSpider
114149
BindingDB
50126701
ChEMBL
CHEMBL24683

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 Solubility0.00985 mg/mLALOGPS
logP4.77ALOGPS
logP5.02Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.73Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area68.23 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity117.08 m3·mol-1Chemaxon
Polarizability44.88 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
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/MSsplash10-00fr-0009100000-05cfe55ecabd8065705d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9805000000-1a027625967818fdb390
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-0209000000-c0402d4efc88473e1da0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-055f-9105000000-4f45f76ed1401bea7059
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-0977100000-77f693734c4f7e6b16d8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003r-3903000000-9e6925c738af5f4239c1
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]-194.96425
predicted
DeepCCS 1.0 (2019)
[M+H]+197.32224
predicted
DeepCCS 1.0 (2019)
[M+Na]+203.94652
predicted
DeepCCS 1.0 (2019)

Targets

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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
References
  1. Chakrabarti R, Vikramadithyan RK, Misra P, Hiriyan J, Raichur S, Damarla RK, Gershome C, Suresh J, Rajagopalan R: Ragaglitazar: a novel PPAR alpha PPAR gamma agonist with potent lipid-lowering and insulin-sensitizing efficacy in animal models. Br J Pharmacol. 2003 Oct;140(3):527-37. Epub 2003 Sep 1. [Article]
  2. Egerod FL, Nielsen HS, Iversen L, Thorup I, Storgaard T, Oleksiewicz MB: Biomarkers for early effects of carcinogenic dual-acting PPAR agonists in rat urinary bladder urothelium in vivo. Biomarkers. 2005 Jul-Aug;10(4):295-309. [Article]
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
References
  1. Chakrabarti R, Vikramadithyan RK, Misra P, Hiriyan J, Raichur S, Damarla RK, Gershome C, Suresh J, Rajagopalan R: Ragaglitazar: a novel PPAR alpha PPAR gamma agonist with potent lipid-lowering and insulin-sensitizing efficacy in animal models. Br J Pharmacol. 2003 Oct;140(3):527-37. Epub 2003 Sep 1. [Article]
  2. Egerod FL, Nielsen HS, Iversen L, Thorup I, Storgaard T, Oleksiewicz MB: Biomarkers for early effects of carcinogenic dual-acting PPAR agonists in rat urinary bladder urothelium in vivo. Biomarkers. 2005 Jul-Aug;10(4):295-309. [Article]

Drug created at March 19, 2008 16:36 / Updated at February 21, 2021 18:52