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Sulfuric acid--4-hydroxy-5-({4-[2-({[6-(4-methoxyphenoxy)pyrimidin-4-yl]methyl}amino)ethoxy]phenyl}methyl)-1,3-thiazol-2(5H)-one (1/1)

HCID 53471697
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Basic information

CAS
763108-62-9
Standard SMILES
COc1ccc(Oc2cc(CNCCOc3ccc(CC4SC(=O)NC4=O)cc3)ncn2)cc1.O=S(=O)(O)O
InChIKey
SZYDFAFNERJCSY-UHFFFAOYSA-N
Molecular formula
C24H26N4O9S2
Average molar mass
578.6 g/mol
Monoisotopic mass
578.11412077

Names & identifiers

Preferred name
Sulfuric acid--4-hydroxy-5-({4-[2-({[6-(4-methoxyphenoxy)pyrimidin-4-yl]methyl}amino)ethoxy]phenyl}methyl)-1,3-thiazol-2(5H)-one (1/1)
IUPAC
5-[[4-[2-[[6-(4-methoxyphenoxy)pyrimidin-4-yl]methylamino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione;sulfuric acid
English name
Lobeglitazone Sulfate
Molecular formula
C24H26N4O9S2
Molecular weight
578.61

Names & synonyms

DTXSID20997665Sulfuric acid--4-hydroxy-5-({4-[2-({[6-(4-methoxyphenoxy)pyrimidin-4-yl]methyl}amino)ethoxy]phenyl}methyl)-1,3-thiazol-2(5H)-one (1/1)5-(4-(2-((6-(4-Methoxyphenoxy)pyrimidin-4-yl)(methyl)amino)ethoxy)benzyl)thiazolidine-2,4-dione sulfateCKD501CKD-501CKD 501Chong Kun DangLobeglitazone SulfateLobeglitazone Sulfate. trade name DuvieLobeglitazone Sulfate. trade name Duvie, Chong Kun Dang

Database identifiers

CAS
763108-62-9
PubChem CID
53471697
DTXSID
DTXSID20997665

Properties

Computed structural properties

Topological polar surface area
220 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
13
Rotatable bonds
11
Heavy atoms
39
Formal charge
0
Complexity
737

Physicochemical properties

form
Solid
color
White to off-white
InChIKey
IFBYQAMJTBOBHB-UHFFFAOYSA-N
SMILES
S(O)(O)(=O)=O.O(C1C=CC(OC)=CC=1)C1=NC=NC(N(C)CCOC2C=CC(CC3C(NC(=O)S3)=O)=CC=2)=C1
FDA UNII
95 C712E83P · 95C712E83P

Chemistry & industry

Applications · 2 items

DescriptionLobeglitazone sulfate, an oral peroxisome proliferator-activated receptor (PPARa/c) dual agonist with IC50 = 20 and 18 nM respectively, was developed by Chong Kun Dang Pharmaceutical in Korea for the treatment of diabetes. This drug is differentiated from two other PPAR agonists available—pioglitazone and rosiglitazone —which lack PPARa activity. The most likely processscale preparation of lobeglitazone sulfate follows the route described in a process communication from Chong Kun Dang Pharmaceutical.

UsesLobeglitazone sulfate is a new type of thiazolidinedione. Lobeglitazone sulfate is the orally active agonist for PPAR with EC50 of 137.4 nM and 546.3 nM for PPARγ and PPARα. Lobeglitazone sulfate is the inhibitor for ERK/JNK/Smad/NF-κB signaling pathway. Lobeglitazone sulfate exhibits anti-inflammatory, anti-diabetic, anti-fibrotic and anti-atherosclerotic properties[1][2][3][4][5][6].

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