Details of the Drug

General Information of Drug (ID: DMPL2KM)

Drug Name
GW-501516
Synonyms
317318-70-0; GW501516; GW 501516; Endurobol; GW-501516; GSK-516; UNII-7I2HA1NU22; GW1516; GW 1516; 2-(2-Methyl-4-(((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methyl)thio)phenoxy)acetic acid; GW-516; GW-1516; CHEMBL38943; 2-(2-methyl-4-((4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)methylthio)phenoxy)acetic acid; 2-(4-((2-(4-(Trifluoromethyl)phenyl)-4-methylthiazol-5-yl)methylthio)-2-methylphenoxy)acetic acid; 7I2HA1NU22
Indication
Disease Entry ICD 11 Status REF
Type-1 diabetes 5A10 Discontinued in Phase 4 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 453.5
Logarithm of the Partition Coefficient (xlogp) 5.9
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C21H18F3NO3S2
IUPAC Name
2-[2-methyl-4-[[4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl]methylsulfanyl]phenoxy]acetic acid
Canonical SMILES
CC1=C(C=CC(=C1)SCC2=C(N=C(S2)C3=CC=C(C=C3)C(F)(F)F)C)OCC(=O)O
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)
InChIKey
YDBLKRPLXZNVNB-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
9803963
ChEBI ID
CHEBI:73726
CAS Number
317318-70-0
UNII
7I2HA1NU22
DrugBank ID
DB05416
TTD ID
D05HDX

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Peroxisome proliferator-activated receptor delta (PPARD) TT2JWF6 PPARD_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Angiopoietin-related protein 4 (ANGPTL4) OTQL5SPX ANGL4_HUMAN Gene/Protein Processing [3]
CX3C chemokine receptor 1 (CX3CR1) OTIM9XT8 CX3C1_HUMAN Gene/Protein Processing [4]
kinase isozyme 4, mitochondrial (PDK4) OTCMHMBZ PDK4_HUMAN Gene/Protein Processing [3]
Oxysterols receptor LXR-alpha (NR1H3) OT54YZ9I NR1H3_HUMAN Gene/Protein Processing [5]
Oxysterols receptor LXR-beta (NR1H2) OT4APA60 NR1H2_HUMAN Gene/Protein Processing [5]
Perilipin-2 (PLIN2) OTRXJ9UN PLIN2_HUMAN Gene/Protein Processing [6]
Peroxisome proliferator-activated receptor alpha (PPARA) OTK095PP PPARA_HUMAN Gene/Protein Processing [5]
Peroxisome proliferator-activated receptor gamma (PPARG) OTHMARHO PPARG_HUMAN Gene/Protein Processing [5]
Peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PPARGC1A) OTHCDQ22 PRGC1_HUMAN Gene/Protein Processing [7]
Phospholipid-transporting ATPase ABCA1 (ABCA1) OT94G6BQ ABCA1_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Type-1 diabetes
ICD Disease Classification 5A10
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Peroxisome proliferator-activated receptor delta (PPARD) DTT PPARD 3.78E-01 9.87E-03 0.06
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2687).
2 Lipid effects of peroxisome proliferator-activated receptor- agonist GW501516 in subjects with low high-density lipoprotein cholesterol: characteristics of metabolic syndrome.Arterioscler Thromb Vasc Biol.2012 Sep;32(9):2289-94.
3 Binding and activity of bisphenol analogues to human peroxisome proliferator-activated receptor /. Ecotoxicol Environ Saf. 2021 Dec 15;226:112849. doi: 10.1016/j.ecoenv.2021.112849. Epub 2021 Oct 6.
4 Rosiglitazone activation of PPARgamma suppresses fractalkine signaling. J Mol Endocrinol. 2010 Feb;44(2):135-42. doi: 10.1677/JME-09-0090. Epub 2009 Oct 22.
5 On the mechanism for PPAR agonists to enhance ABCA1 gene expression. Atherosclerosis. 2009 Aug;205(2):413-9. doi: 10.1016/j.atherosclerosis.2009.01.008. Epub 2009 Jan 19.
6 Role of Peroxisome Proliferator-Activated Receptor / and B-Cell Lymphoma-6 in Regulation of Genes Involved in Metastasis and Migration in Pancreatic Cancer Cells. PPAR Res. 2013;2013:121956. doi: 10.1155/2013/121956. Epub 2013 May 2.
7 A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1 expression and mitochondrial biogenesis. PLoS One. 2012;7(10):e46753. doi: 10.1371/journal.pone.0046753. Epub 2012 Oct 3.