Identification
- Generic Name
- Elafibranor
- DrugBank Accession Number
- DB05187
- Background
Elafibranor (code name GFT505) is a multimodal and pluripotent medication for treatment of atherogenic dyslipidemia for an overweight patient with or without diabetes. It is an oral treatment that acts on the 3 sub-types of PPAR (PPARa, PPARg, PPARd) with a preferential action on PPARa. As of February 2016, elafibranor has completed 8 clinical trials and a phase III is in progress.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Elafibranor (DB05187)
- Weight
- Average: 384.49
Monoisotopic: 384.139530427 - Chemical Formula
- C22H24O4S
- Synonyms
- Elafibranor
- External IDs
- GFT-505
- GFT505
Pharmacology
- Indication
Investigated for use/treatment in atherosclerosis and diabetes mellitus type 2.
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Not Available
- Mechanism of action
GFT505 is an oral treatment that acts on the 3 sub-types of PPAR (PPARa, PPARg, PPARd) with a preferential action on PPARa. It has a sophisticated mechanism of action. It is able to differentially recruit cofactors to the nuclear receptor, which subsequently lead to differential regulation of genes and biological effect. Therefore, the ability to identify and profile the activity of selective nuclear receptor modulator (SNuRMs) is a powerful approach to select innovative drug candidates with improved efficacy and diminished side effects. These pluripotent and multimodal molecules have significant positive effects on obesity, insulin-resistance and diabetes, atherosclerosis, inflammation, and the lipid triad (increasing of HDL cholesterol, lowering of triglycerides and LDL cholesterol).
Target Actions Organism UPeroxisome proliferator-activated receptor alpha Not Available Humans UPeroxisome proliferator-activated receptor delta Not Available Humans UPeroxisome proliferator-activated receptor gamma Not Available Humans - 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 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.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 retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Linear 1,3-diarylpropanoids
- Sub Class
- Chalcones and dihydrochalcones
- Direct Parent
- Retrochalcones
- Alternative Parents
- Cinnamic acids and derivatives / Phenoxyacetic acid derivatives / Aryl ketones / Benzoyl derivatives / m-Xylenes / Phenol ethers / Phenoxy compounds / Thiophenol ethers / Styrenes / Alkyl aryl ethers show 8 more
- Substituents
- Acryloyl-group / Alkyl aryl ether / Alkylarylthioether / Alpha,beta-unsaturated ketone / Aromatic homomonocyclic compound / Aryl ketone / Aryl thioether / Benzenoid / Benzoyl / Carbonyl group show 23 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 2J3H5C81A5
- CAS number
- 923978-27-2
- InChI Key
- AFLFKFHDSCQHOL-IZZDOVSWSA-N
- InChI
- InChI=1S/C22H24O4S/c1-14-12-16(13-15(2)20(14)26-22(3,4)21(24)25)6-11-19(23)17-7-9-18(27-5)10-8-17/h6-13H,1-5H3,(H,24,25)/b11-6+
- IUPAC Name
- 2-{2,6-dimethyl-4-[(1E)-3-[4-(methylsulfanyl)phenyl]-3-oxoprop-1-en-1-yl]phenoxy}-2-methylpropanoic acid
- SMILES
- CSC1=CC=C(C=C1)C(=O)\C=C\C1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 9864881
- PubChem Substance
- 347827716
- ChemSpider
- 8040573
- ChEMBL
- CHEMBL3707395
- ZINC
- ZINC000114643710
- PDBe Ligand
- MUO
- Wikipedia
- Elafibranor
- PDB Entries
- 8huq
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Active Not Recruiting Treatment Primary Biliary Cholangitis 1 3 Recruiting Treatment Primary Biliary Cholangitis 1 3 Terminated Treatment Nonalcoholic Steatohepatitis (NASH) With Fibrosis 1 2 Completed Treatment Atherogenic Dyslipidemia / Obesity, Abdominal 1 2 Completed Treatment Impaired Glucose Tolerance / Obesity, Abdominal 1
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 0.000228 mg/mL ALOGPS logP 4.6 ALOGPS logP 5.87 Chemaxon logS -6.2 ALOGPS pKa (Strongest Acidic) 4 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 63.6 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 111.47 m3·mol-1 Chemaxon Polarizability 43.14 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-7179000000-d443aeafa71832b02712 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6t-0090000000-b92649bf44b475172401 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0592-4592000000-fa14fb12f087ae87efc9 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-003r-1890000000-264993b76eef063e7a48 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0pb9-1930000000-11000462d9978f9a7f32 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-000t-3291000000-76334ceb4b30aaf5f080 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Not Available
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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Ligand-activated transcription factor. Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Has a preference for poly-unsaturated fatty acids, such as gamma-lin...
- Gene Name
- PPARD
- Uniprot ID
- Q03181
- Uniprot Name
- Peroxisome proliferator-activated receptor delta
- Molecular Weight
- 49902.99 Da
- 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 22:24 / Updated at February 21, 2021 18:51