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Details

Stereochemistry ACHIRAL
Molecular Formula C25H25N3O4S
Molecular Weight 463.5507
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SIPOGLITAZAR

SMILES

CCOc1c(CCC(=O)O)cn(Cc2ccc(cc2)OCc3csc(-c4ccccc4)n3)n1

InChI

InChIKey=SRFCAWATPLCLMG-UHFFFAOYSA-N
InChI=1S/C25H25N3O4S/c1-2-31-24-20(10-13-23(29)30)15-28(27-24)14-18-8-11-22(12-9-18)32-16-21-17-33-25(26-21)19-6-4-3-5-7-19/h3-9,11-12,15,17H,2,10,13-14,16H2,1H3,(H,29,30)

HIDE SMILES / InChI

Molecular Formula C25H25N3O4S
Molecular Weight 463.5507
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Sipoglitazar (TAK 654) was a novel, azolealkanoic acid derivative that possesses selective activity for the peroxisome proliferator-activated receptors (PPAR) PPARγ, PPARα, and PPARδ. Sipoglitazar was developed to improve peripheral insulin sensitivity, normalize circulating lipid profiles, and reduce body weight in patients with metabolic syndrome and type 2 diabetes mellitus (T2DM). Sipoglitazar was being developed by Takeda for the treatment of diabetes mellitus, however in September 2006, development was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolic fate of sipoglitazar, a novel oral PPAR agonist with activities for PPAR-γ, -α and -δ, in rats and monkeys and comparison with humans in vitro.
2012
An unusual metabolic pathway of sipoglitazar, a novel antidiabetic agent: cytochrome P450-catalyzed oxidation of sipoglitazar acyl glucuronide.
2012 Feb
UDP-glucuronosyltransferase 2B15 (UGT2B15) is the major enzyme responsible for sipoglitazar glucuronidation in humans: retrospective identification of the UGT isoform by in vitro analysis and the effect of UGT2B15*2 mutation.
2013
The effect of genetic polymorphisms in UGT2B15 on the pharmacokinetic profile of sipoglitazar, a novel anti-diabetic agent.
2013 Mar
Patents

Patents

Sample Use Guides

In the ascending dose part of the study, 48 subjects received one dose of placebo and two single doses of sipoglitazar at doses of 0.2, 0.4, 1, 2, 4, 8, 16, 32, and 64 mg. In male subjects, single oral doses of sipoglitazar, 0.2–64 mg, were well tolerated, as were single oral doses of 16–64 mg in female subjects.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:09:01 UTC 2021
Edited
by admin
on Sat Jun 26 03:09:01 UTC 2021
Record UNII
40O898CJZB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SIPOGLITAZAR
INN  
INN  
Official Name English
3-(3-ETHOXY-1-(4-((2-PHENYL-1,3-THIAZOL-4-YL)METHOXY)BENZYL)-1H-PYRAZOL-4-YL)PROPANOIC ACID
Systematic Name English
TAK-654
Code English
SIPOGLITAZAR [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98233
Created by admin on Sat Jun 26 03:09:01 UTC 2021 , Edited by admin on Sat Jun 26 03:09:01 UTC 2021
Code System Code Type Description
INN
8610
Created by admin on Sat Jun 26 03:09:01 UTC 2021 , Edited by admin on Sat Jun 26 03:09:01 UTC 2021
PRIMARY
NCI_THESAURUS
C87622
Created by admin on Sat Jun 26 03:09:01 UTC 2021 , Edited by admin on Sat Jun 26 03:09:01 UTC 2021
PRIMARY
FDA UNII
40O898CJZB
Created by admin on Sat Jun 26 03:09:01 UTC 2021 , Edited by admin on Sat Jun 26 03:09:01 UTC 2021
PRIMARY
ChEMBL
CHEMBL2107780
Created by admin on Sat Jun 26 03:09:01 UTC 2021 , Edited by admin on Sat Jun 26 03:09:01 UTC 2021
PRIMARY
PUBCHEM
9825652
Created by admin on Sat Jun 26 03:09:01 UTC 2021 , Edited by admin on Sat Jun 26 03:09:01 UTC 2021
PRIMARY
CAS
342026-92-0
Created by admin on Sat Jun 26 03:09:01 UTC 2021 , Edited by admin on Sat Jun 26 03:09:01 UTC 2021
PRIMARY
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