SIPOGLITAZAR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C25H25N3O4S
Molecular Weight	463.549
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=NN(CC2=CC=C(OCC3=CSC(=N3)C4=CC=CC=C4)C=C2)C=C1CCC(O)=O

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

Description
Sources: https://adisinsight.springer.com/drugs/800020142 | https://www.ncbi.nlm.nih.gov/pubmed/22960998

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxisome proliferator-activated receptor alpha 62 Target ID: CHEMBL239 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22123126	Agonist 2678
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22123126	Agonist 2678
Peroxisome proliferator-activated receptor delta 29 Target ID: CHEMBL3979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22123126	Agonist 2678

PubMed

Title	Date	PubMed
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	22123126
An unusual metabolic pathway of sipoglitazar, a novel antidiabetic agent: cytochrome P450-catalyzed oxidation of sipoglitazar acyl glucuronide.	2012 Feb	22028317
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	23648677
The effect of genetic polymorphisms in UGT2B15 on the pharmacokinetic profile of sipoglitazar, a novel anti-diabetic agent.	2013 Mar	22960998

Patents

Sample Use Guides

In Vivo Use Guide

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

Name

Type

Language

SIPOGLITAZAR

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