This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
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
Structure for Tesaglitazar (DB06536)
- 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.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Target Actions Organism APeroxisome proliferator-activated receptor gamma modulatorHumans APeroxisome proliferator-activated receptor alpha modulatorHumans - 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 outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
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- 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
- 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]
- 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]
- External Links
- PubChem Compound
- 208901
- ChemSpider
- 180999
- BindingDB
- 28798
- ChEMBL
- CHEMBL282686
- ZINC
- ZINC000001550769
- PDBe Ligand
- AZ2
- Wikipedia
- Tesaglitazar
- PDB Entries
- 1i7g / 1i7i
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Terminated Treatment Type 2 Diabetes Mellitus 13 somestatus stop reason just information to hide 2 Completed Treatment Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide 2 Terminated Not Available Type 2 Diabetes Mellitus 1 somestatus stop reason just information to hide 2 Terminated Treatment Type 2 Diabetes Mellitus 2 somestatus stop reason just information to hide
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
Property Value Source Water Solubility 0.00351 mg/mL ALOGPS logP 3.18 ALOGPS logP 3.14 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 3.73 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 99.13 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 103.52 m3·mol-1 Chemaxon Polarizability 42.56 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9156 Blood Brain Barrier + 0.8918 Caco-2 permeable - 0.6095 P-glycoprotein substrate Non-substrate 0.5288 P-glycoprotein inhibitor I Inhibitor 0.5859 P-glycoprotein inhibitor II Non-inhibitor 0.9059 Renal organic cation transporter Non-inhibitor 0.7945 CYP450 2C9 substrate Non-substrate 0.813 CYP450 2D6 substrate Non-substrate 0.8296 CYP450 3A4 substrate Substrate 0.598 CYP450 1A2 substrate Non-inhibitor 0.7271 CYP450 2C9 inhibitor Non-inhibitor 0.7522 CYP450 2D6 inhibitor Non-inhibitor 0.8978 CYP450 2C19 inhibitor Non-inhibitor 0.6884 CYP450 3A4 inhibitor Non-inhibitor 0.9581 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8034 Ames test AMES toxic 0.5309 Carcinogenicity Carcinogens 0.5139 Biodegradation Not ready biodegradable 0.6566 Rat acute toxicity 2.1971 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7874 hERG inhibition (predictor II) Inhibitor 0.5843
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-02t9-0009000000-90a0926a095e689b747f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9006000000-45bb2db476f183737343 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014j-0129000000-fd580e63eeeca87b90fd Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-067l-9005000000-bd6e748863ee68ae9b98 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05r0-9016100000-4d6dd7d6eb9d0ac216fe Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0hn0-0987100000-73f4d65788a6b5cead38 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 188.10562 predictedDeepCCS 1.0 (2019) [M+H]+ 190.46362 predictedDeepCCS 1.0 (2019) [M+Na]+ 197.96971 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General 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) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated pro-inflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of BMAL1 in the blood vessels (By similarity)
- Specific Function
- alpha-actinin binding
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 Da
References
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General 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 oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as a transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2
- Specific Function
- DNA binding
- Gene Name
- PPARA
- Uniprot ID
- Q07869
- Uniprot Name
- Peroxisome proliferator-activated receptor alpha
- Molecular Weight
- 52224.595 Da
References
- 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at March 19, 2008 16:36 / Updated at August 26, 2024 19:23