Synonym
DS-1558; DS 1558; DS1558.
IUPAC/Chemical Name
(S)-3-ethoxy-3-(4-(((R)-4-(trifluoromethyl)-2,3-dihydro-1H-inden-1-yl)oxy)phenyl)propanoic acid
InChi Key
YHLQVQKZDZYMIP-MOPGFXCFSA-N
InChi Code
InChI=1S/C21H21F3O4/c1-2-27-19(12-20(25)26)13-6-8-14(9-7-13)28-18-11-10-15-16(18)4-3-5-17(15)21(22,23)24/h3-9,18-19H,2,10-12H2,1H3,(H,25,26)/t18-,19+/m1/s1
SMILES Code
FC(F)(F)C1=CC=CC2=C1CC[C@H]2OC(C=C3)=CC=C3[C@H](CC(O)=O)OCC
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, not in water
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
394.39
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: Takano R, Yoshida M, Inoue M, Honda T, Nakashima R, Matsumoto K, Yano T, Ogata
T, Watanabe N, Hirouchi M, Kimura T, Toda N. Optimization of
3-aryl-3-ethoxypropanoic acids and discovery of the potent GPR40 agonist DS-1558.
Bioorg Med Chem. 2015 Sep 1;23(17):5546-65. doi: 10.1016/j.bmc.2015.07.028. Epub
2015 Jul 23. PubMed PMID: 26234904.
2: Takano R, Yoshida M, Inoue M, Honda T, Nakashima R, Matsumoto K, Yano T, Ogata
T, Watanabe N, Hirouchi M, Yoneyama T, Ito S, Toda N. Discovery of DS-1558: A
Potent and Orally Bioavailable GPR40 Agonist. ACS Med Chem Lett. 2015 Jan
13;6(3):266-70. doi: 10.1021/ml500391n. eCollection 2015 Mar 12. PubMed PMID:
25815144; PubMed Central PMCID: PMC4360146.
3: Nakashima R, Yano T, Ogawa J, Tanaka N, Toda N, Yoshida M, Takano R, Inoue M,
Honda T, Kume S, Matsumoto K. Potentiation of insulin secretion and improvement
of glucose intolerance by combining a novel G protein-coupled receptor 40 agonist
DS-1558 with glucagon-like peptide-1 receptor agonists. Eur J Pharmacol. 2014 Aug
15;737:194-201. doi: 10.1016/j.ejphar.2014.05.014. Epub 2014 May 22. PubMed PMID:
24858371.
