Cardarine
Identification
- Generic Name
- Cardarine
- DrugBank Accession Number
- DB05416
- Background
Cardarine (GW-501516) is a peroxisome proliferator-activator receptor-delta agonist for the potential treatment of dyslipidemia. Cardarine has been investigated for the treatment of Obesity, Lipid Disorders, and Cardiovascular Disease.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 453.498
Monoisotopic: 453.068019442 - Chemical Formula
- C21H18F3NO3S2
- Synonyms
- Not Available
- External IDs
- GSK-516
- GW-1516
- GW-501516
- GW501516
Pharmacology
- Indication
Investigated for use/treatment in hyperlipidemia.
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- Pharmacodynamics
Not Available
- Mechanism of action
This drug regulates fatty acid oxidation in several tissues, such as skeletal muscle and adipose tissue. Overexpression of PPARdelta using a transgenic murine model promotes an increase of muscle oxidative capability. It also plays a major role in the metabolic adaptations to western diet characterized by an excessive amount of saturated fat.
Target Actions Organism UPeroxisome proliferator-activated receptor delta agonistHumans UPeroxisome proliferator-activated receptor alpha agonistHumans - 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
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenoxyacetic acid derivatives
- Direct Parent
- Phenoxyacetic acid derivatives
- Alternative Parents
- Trifluoromethylbenzenes / Thiophenol ethers / Phenoxy compounds / Phenol ethers / 2,4,5-trisubstituted thiazoles / Toluenes / Alkyl aryl ethers / Alkylarylthioethers / Heteroaromatic compounds / Sulfenyl compounds show 10 more
- Substituents
- 2,4,5-trisubstituted 1,3-thiazole / Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Alkylarylthioether / Aromatic heteromonocyclic compound / Aryl thioether / Azacycle / Azole / Carbonyl group show 25 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organofluorine compound, aromatic ether, monocarboxylic acid, aryl sulfide, 1,3-thiazole (CHEBI:73726)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7I2HA1NU22
- CAS number
- 317318-70-0
- InChI Key
- YDBLKRPLXZNVNB-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H18F3NO3S2/c1-12-9-16(7-8-17(12)28-10-19(26)27)29-11-18-13(2)25-20(30-18)14-3-5-15(6-4-14)21(22,23)24/h3-9H,10-11H2,1-2H3,(H,26,27)
- IUPAC Name
- 2-{2-methyl-4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)sulfanyl]phenoxy}acetic acid
- SMILES
- CC1=C(CSC2=CC(C)=C(OCC(O)=O)C=C2)SC(=N1)C1=CC=C(C=C1)C(F)(F)F
References
- General References
- Dimopoulos N, Watson M, Green C, Hundal HS: The PPARdelta agonist, GW501516, promotes fatty acid oxidation but has no direct effect on glucose utilisation or insulin sensitivity in rat L6 skeletal muscle cells. FEBS Lett. 2007 Oct 2;581(24):4743-8. Epub 2007 Sep 6. [Article]
- Kramer DK, Al-Khalili L, Guigas B, Leng Y, Garcia-Roves PM, Krook A: Role of AMP kinase and PPARdelta in the regulation of lipid and glucose metabolism in human skeletal muscle. J Biol Chem. 2007 Jul 6;282(27):19313-20. Epub 2007 May 11. [Article]
- Fredenrich A, Grimaldi PA: PPAR delta: an uncompletely known nuclear receptor. Diabetes Metab. 2005 Feb;31(1):23-7. [Article]
- External Links
- PubChem Compound
- 9803963
- PubChem Substance
- 175426999
- ChemSpider
- 7979723
- BindingDB
- 28661
- ChEBI
- 73726
- ChEMBL
- CHEMBL38943
- ZINC
- ZINC000001549989
- PDBe Ligand
- 7T1
- Wikipedia
- GW501516
- PDB Entries
- 5u46
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Cardiovascular Disease (CVD) / Lipid Disorders / Obesity 1 2 Completed Treatment Dyslipidemia 1 Not Available Completed Not Available Dyslipidemia / High Cholesterol / Obesity 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 0.000325 mg/mL ALOGPS logP 5.43 ALOGPS logP 5.7 Chemaxon logS -6.2 ALOGPS pKa (Strongest Acidic) 3.51 Chemaxon pKa (Strongest Basic) 2.14 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 59.42 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 121.88 m3·mol-1 Chemaxon Polarizability 43.38 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9873 Blood Brain Barrier + 0.8877 Caco-2 permeable + 0.5 P-glycoprotein substrate Non-substrate 0.5964 P-glycoprotein inhibitor I Non-inhibitor 0.785 P-glycoprotein inhibitor II Non-inhibitor 0.5719 Renal organic cation transporter Non-inhibitor 0.7909 CYP450 2C9 substrate Non-substrate 0.765 CYP450 2D6 substrate Non-substrate 0.7962 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Inhibitor 0.6861 CYP450 2C9 inhibitor Inhibitor 0.6573 CYP450 2D6 inhibitor Non-inhibitor 0.8321 CYP450 2C19 inhibitor Inhibitor 0.7816 CYP450 3A4 inhibitor Inhibitor 0.7843 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9405 Ames test Non AMES toxic 0.696 Carcinogenicity Non-carcinogens 0.8219 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6222 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9993 hERG inhibition (predictor II) Non-inhibitor 0.6917
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udu-0030900000-ab669d10da385e61cd45 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-1300900000-8ac927e77a59ef35db28 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-052r-1011900000-11acbfc2c1363b6f158c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0611900000-ec73ced4f7dea9b5df4c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-052u-4891200000-8f0dfec041d569160153 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00b9-9600000000-435ee0f2f24ad902a7de 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]- 200.08481 predictedDeepCCS 1.0 (2019) [M+H]+ 202.44281 predictedDeepCCS 1.0 (2019) [M+Na]+ 209.93896 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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
References
- Buhrke T, Kibellus A, Lampen A: In vitro toxicological characterization of perfluorinated carboxylic acids with different carbon chain lengths. Toxicol Lett. 2013 Apr 12;218(2):97-104. doi: 10.1016/j.toxlet.2013.01.025. Epub 2013 Feb 4. [Article]
- Sarath Josh MK, Pradeep S, Vijayalekshmi Amma KS, Balachandran S, Abdul Jaleel UC, Doble M, Spener F, Benjamin S: Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor alpha, beta, gamma subtypes: an in silico approach. J Appl Toxicol. 2014 Jul;34(7):754-65. doi: 10.1002/jat.2902. Epub 2013 Jul 11. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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
- Sarath Josh MK, Pradeep S, Vijayalekshmi Amma KS, Balachandran S, Abdul Jaleel UC, Doble M, Spener F, Benjamin S: Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor alpha, beta, gamma subtypes: an in silico approach. J Appl Toxicol. 2014 Jul;34(7):754-65. doi: 10.1002/jat.2902. Epub 2013 Jul 11. [Article]
Drug created at November 18, 2007 18:24 / Updated at June 12, 2020 16:52