Synonym
Sipoglitazar, TAK-654; TAK 654; TAK654.
IUPAC/Chemical Name
3-(3-Ethoxy-1-(4-((2-phenyl-1,3-thiazol-4-yl)methoxy)benzyl)-1H-pyrazol-4-yl)propanoic acid
InChi Key
SRFCAWATPLCLMG-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(O)CCC1=CN(CC2=CC=C(OCC3=CSC(C4=CC=CC=C4)=N3)C=C2)N=C1OCC
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
463.55
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Stringer F, DeJongh J, Scott G, Danhof M. A model-based approach to analyze the influence of UGT2B15 polymorphism driven pharmacokinetic differences on the pharmacodynamic response of the PPAR agonist sipoglitazar. J Clin Pharmacol. 2014 Apr;54(4):453-61. doi: 10.1002/jcph.227. PubMed PMID: 24214217.
2: Nishihara M, Hiura Y, Kawaguchi N, Takahashi J, Asahi S. 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. Drug Metab Pharmacokinet. 2013;28(6):475-84. PubMed PMID: 23648677.
3: Stringer F, Ploeger BA, DeJongh J, Scott G, Urquhart R, Karim A, Danhof M. Evaluation of the impact of UGT polymorphism on the pharmacokinetics and pharmacodynamics of the novel PPAR agonist sipoglitazar. J Clin Pharmacol. 2013 Mar;53(3):256-63. doi: 10.1177/0091270012447121. PubMed PMID: 23444281.
4: Stringer F, Scott G, Valbuena M, Kinley J, Nishihara M, Urquhart R. The effect of genetic polymorphisms in UGT2B15 on the pharmacokinetic profile of sipoglitazar, a novel anti-diabetic agent. Eur J Clin Pharmacol. 2013 Mar;69(3):423-30. doi: 10.1007/s00228-012-1382-7. PubMed PMID: 22960998.
5: Nishihara M, Sudo M, Kamiguchi H, Kawaguchi N, Maeshiba Y, Kiyota Y, Takahashi J, Tagawa Y, Kondo T, Asahi S. 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. Drug Metab Pharmacokinet. 2012;27(2):223-31. PubMed PMID: 22123126.
6: Nishihara M, Sudo M, Kawaguchi N, Takahashi J, Kiyota Y, Kondo T, Asahi S. An unusual metabolic pathway of sipoglitazar, a novel antidiabetic agent: cytochrome P450-catalyzed oxidation of sipoglitazar acyl glucuronide. Drug Metab Dispos. 2012 Feb;40(2):249-58. doi: 10.1124/dmd.111.040105. PubMed PMID: 22028317.
