NAV

Tesaglitazar

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

Identification

Generic Name
Tesaglitazar
DrugBank Accession Number
DB06536
Background

Tesaglitazar is a dual peroxisome proliferator-activated receptor alpha/gamma agonist which improves apolipoprotein levels in non-diabetic subjects with insulin resistance. Tesaglitazar is a proposed treatment for type 2 diabetes and has completed several phase III clinical trials, however in May 2006 AstraZeneca announced that they had discontinued further development.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 408.465
Monoisotopic: 408.124273812
Chemical Formula
C20H24O7S
Synonyms
  • Tesaglitazar
External IDs
  • AR-H-039242
  • AR-H039242XX
  • AZ-242
  • BR-44608

Pharmacology

Indication

Investigated for use/treatment in diabetes mellitus type 2.

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Treatment with tesaglitazar lowered fasting plasma glucose, improved glucose tolerance, substantially reduced fasting and postload insulin levels, and markedly lowered fasting TG and improved lipid tolerance.

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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
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

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Galida (AstraZeneca)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Phenylpropanoic acids
Sub Class
Not Available
Direct Parent
Phenylpropanoic acids
Alternative Parents
Tyrosols and derivatives / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Sulfonic acid esters / Organosulfonic acid esters / Sulfonyls / Methanesulfonates / Monocarboxylic acids and derivatives / Dialkyl ethers
show 4 more
Substituents
3-phenylpropanoic-acid / Alkyl aryl ether / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Ether / Hydrocarbon derivative
show 15 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6734037O3L
CAS number
251565-85-2
InChI Key
CXGTZJYQWSUFET-IBGZPJMESA-N
InChI
InChI=1S/C20H24O7S/c1-3-25-19(20(21)22)14-16-6-8-17(9-7-16)26-13-12-15-4-10-18(11-5-15)27-28(2,23)24/h4-11,19H,3,12-14H2,1-2H3,(H,21,22)/t19-/m0/s1
IUPAC Name
(2S)-2-ethoxy-3-(4-{2-[4-(methanesulfonyloxy)phenyl]ethoxy}phenyl)propanoic acid
SMILES
CCO[C@@H](CC1=CC=C(OCCC2=CC=C(OS(C)(=O)=O)C=C2)C=C1)C(O)=O

References

General References
  1. Oakes ND, Thalen P, Hultstrand T, Jacinto S, Camejo G, Wallin B, Ljung B: Tesaglitazar, a dual PPAR{alpha}/{gamma} agonist, ameliorates glucose and lipid intolerance in obese Zucker rats. Am J Physiol Regul Integr Comp Physiol. 2005 Oct;289(4):R938-46. [Article]
  2. Schuster H, Fagerberg B, Edwards S, Halmos T, Lopatynski J, Stender S, Birketvedt GS, Tonstad S, Gause-Nilsson I, Halldorsdottir S, Ohman KP: Tesaglitazar, a dual peroxisome proliferator-activated receptor alpha/gamma agonist, improves apolipoprotein levels in non-diabetic subjects with insulin resistance. Atherosclerosis. 2008 Mar;197(1):355-62. Epub 2007 Jul 13. [Article]
PubChem Compound
208901
ChemSpider
180999
BindingDB
28798
ChEMBL
CHEMBL282686
ZINC
ZINC000001550769
PDBe Ligand
AZ2
Wikipedia
Tesaglitazar
PDB Entries
1i7g / 1i7i

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentType 2 Diabetes Mellitus13
2CompletedTreatmentType 2 Diabetes Mellitus1
2TerminatedNot AvailableType 2 Diabetes Mellitus1
2TerminatedTreatmentType 2 Diabetes Mellitus2

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 Solubility0.00351 mg/mLALOGPS
logP3.18ALOGPS
logP3.14Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.73Chemaxon
pKa (Strongest Basic)-4.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area99.13 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity103.52 m3·mol-1Chemaxon
Polarizability42.56 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.8918
Caco-2 permeable-0.6095
P-glycoprotein substrateNon-substrate0.5288
P-glycoprotein inhibitor IInhibitor0.5859
P-glycoprotein inhibitor IINon-inhibitor0.9059
Renal organic cation transporterNon-inhibitor0.7945
CYP450 2C9 substrateNon-substrate0.813
CYP450 2D6 substrateNon-substrate0.8296
CYP450 3A4 substrateSubstrate0.598
CYP450 1A2 substrateNon-inhibitor0.7271
CYP450 2C9 inhibitorNon-inhibitor0.7522
CYP450 2D6 inhibitorNon-inhibitor0.8978
CYP450 2C19 inhibitorNon-inhibitor0.6884
CYP450 3A4 inhibitorNon-inhibitor0.9581
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8034
Ames testAMES toxic0.5309
CarcinogenicityCarcinogens 0.5139
BiodegradationNot ready biodegradable0.6566
Rat acute toxicity2.1971 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7874
hERG inhibition (predictor II)Inhibitor0.5843
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 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

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
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
References
  1. Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [Article]
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
References
  1. Tenenbaum A, Motro M, Fisman EZ: Dual and pan-peroxisome proliferator-activated receptors (PPAR) co-agonism: the bezafibrate lessons. Cardiovasc Diabetol. 2005 Sep 16;4:14. [Article]

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