Details of the Drug

General Information of Drug (ID: DM1SLJ9)

Drug Name
AD-5075
Synonyms
2,4-Thiazolidinedione, 5-((4-(2-hydroxy-2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy)phenyl)methyl)-; AD 5075; 103788-05-2; 5-[[4-[2-hydroxy-2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione; 2,4-Thiazolidinedione,5-[[4-[2-hydroxy-2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]methyl]-; YVQKIDLSVHRBGZ-UHFFFAOYSA-N; [3H]AD5075; [3H]-AD5075; ACMC-20m6lh; AC1L2TSO; CHEMBL88496; SCHEMBL131888; GTPL2702; GTPL2701; CTK4A2384; AD5075; 5-(4-(2-(5-Methyl-2-phenyl-4-oxazolyl)-2-hydroxyethoxy)benzyl)-2,4-thiazolidinedione; [3H]AD-5075
Indication
Disease Entry ICD 11 Status REF
Type-2 diabetes 5A11 Terminated [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 424.5
Topological Polar Surface Area (xlogp) 3.4
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 7
Chemical Identifiers
Formula
C22H20N2O5S
IUPAC Name
5-[[4-[2-hydroxy-2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Canonical SMILES
CC1=C(N=C(O1)C2=CC=CC=C2)C(COC3=CC=C(C=C3)CC4C(=O)NC(=O)S4)O
InChI
InChI=1S/C22H20N2O5S/c1-13-19(23-21(29-13)15-5-3-2-4-6-15)17(25)12-28-16-9-7-14(8-10-16)11-18-20(26)24-22(27)30-18/h2-10,17-18,25H,11-12H2,1H3,(H,24,26,27)
InChIKey
YVQKIDLSVHRBGZ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
128440
CAS Number
103788-05-2
TTD ID
D0LB4T

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Peroxisome proliferator-activated receptor gamma (PPAR-gamma) TTZMAO3 PPARG_HUMAN Modulator [2]
PPAR-gamma messenger RNA (PPARG mRNA) TTT2SVW PPARG_HUMAN Agonist [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Type-2 diabetes
ICD Disease Classification 5A11
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Peroxisome proliferator-activated receptor gamma (PPAR-gamma) DTT PPARG 2.41E-01 -0.06 -0.25
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: 2701).
2 Thiazolidinediones produce a conformational change in peroxisomal proliferator-activated receptor-gamma: binding and activation correlate with antidiabetic actions in db/db mice. Endocrinology. 1996 Oct;137(10):4189-95.
3 A synthetic triterpenoid, 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), is a ligand for the peroxisome proliferator-activated receptor gamma. Mol Endocrinol. 2000 Oct;14(10):1550-6.
4 Tryptophan-containing dipeptide derivatives as potent PPARgamma antagonists: design, synthesis, biological evaluation, and molecular modeling. Eur J Med Chem. 2008 Dec;43(12):2699-716.
5 Novel peroxisome proliferator-activated receptor (PPAR) gamma and PPARdelta ligands produce distinct biological effects. J Biol Chem. 1999 Mar 5;274(10):6718-25.
6 The antidiabetic agent LG100754 sensitizes cells to low concentrations of peroxisome proliferator-activated receptor gamma ligands. J Biol Chem. 2002 Apr 12;277(15):12503-6.
7 Phenylacetic acid derivatives as hPPAR agonists. Bioorg Med Chem Lett. 2003 Apr 7;13(7):1277-80.
8 A novel oxyiminoalkanoic acid derivative, TAK-559, activates human peroxisome proliferator-activated receptor subtypes. Eur J Pharmacol. 2004 Jul 8;495(1):17-26.
9 A novel peroxisome proliferator-activated receptor alpha/gamma dual agonist demonstrates favorable effects on lipid homeostasis. Endocrinology. 2004 Apr;145(4):1640-8.
10 Activation of peroxisome proliferator-activated receptor gamma (PPARgamma) by nitroalkene fatty acids: importance of nitration position and degree ... J Med Chem. 2009 Aug 13;52(15):4631-9.
11 Pharmacological profiles of a novel oral antidiabetic agent, JTT-501, an isoxazolidinedione derivative. Eur J Pharmacol. 1999 Jan 8;364(2-3):211-9.
12 Expression of peroxisome proliferator-activated receptors (PPARs) in human urinary bladder carcinoma and growth inhibition by its agonists. Int J Cancer. 2003 May 1;104(5):597-602.
13 Functional PPAR-gamma receptor is a novel therapeutic target for ACTH-secreting pituitary adenomas. Nat Med. 2002 Nov;8(11):1281-7.
14 Tolerability and pharmacokinetics of lobeglitazone, a novel peroxisome proliferator-activated receptor-gamma agonist, after a single oral administration in healthy female subjects. Clin Drug Investig. 2014 Jul;34(7):467-74.
15 Clinical pipeline report, company report or official report of GlaxoSmithKline (2009).
16 Peroxisome proliferator-activated receptor alpha activators improve insulin sensitivity and reduce adiposity. J Biol Chem. 2000 Jun 2;275(22):16638-42.
17 Muraglitazar, a dual (alpha/gamma) PPAR activator: a randomized, double-blind, placebo-controlled, 24-week monotherapy trial in adult patients with... Clin Ther. 2005 Aug;27(8):1181-95.
18 A randomized-controlled trial to investigate the effects of rivoglitazone, a novel PPAR gamma agonist on glucose-lipid control in type 2 diabetes. Diabetes Obes Metab. 2011 Sep;13(9):806-13.
19 Balaglitazone: a second generation peroxisome proliferator-activated receptor (PPAR) gamma () agonist.Mini Rev Med Chem.2012 Feb;12(2):87-97.