CAS No. : 1000413-72-8

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For research use only. Not Intended for Therapeutic Use!
Cat No:I000065
Synonyms:2-[(3S)-6-[[3-[2,6-dimethyl-4-(3-methylsulfonylpropoxy)phenyl]phenyl]methoxy]-2,3-dihydro-1-benzofuran-3-yl]acetic acid
Molecular Formula:C29H32O7S
Molecular Weight:524.6
Target:Free fatty acid receptor 1 (FFAR1; GPR40)
IC50:0.072 μM(EC50)
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Appearance:white to off-white solid powder
Purity: > 98%
Cat No:I000065
Cas No:1000413-72-8

TAK-875(cas 1000413-72-8) is a potent, selective and orally bioavailable GPR40 agonist with EC50 of 0.072 μM.

TAK-875 showed potent plasma glucose-lowering action and insulinotropic action during an oral glucose tolerance test in female Wistar fatty rats with impaired glucose tolerance. TAK-875 is currently in clinical trials for the treatment of type 2 diabetes mellitus. It was withdrawn from Phase III clinical trials due to drug-induced liver injury (DILI).

1. Diabetes Obes Metab. 2012 Mar;14(3):271-8. doi: 10.1111/j.1463-1326.2011.01525.x. Epub 2011 Dec 22.
GPR40-induced insulin secretion by the novel agonist TAK-875: first clinical findings in patients with type 2 diabetes.
Araki T(1), Hirayama M, Hiroi S, Kaku K.
Author information:
(1)Pharmaceutical Development Division, Takeda Pharmaceutical Company Limited, Osaka, Japan. takahiro.araki@tgrd.com
AIM: Free fatty acids act as signalling molecules for modulating insulin secretion, and their insulinotropic effects are glucose-dependent and mediated through G protein-coupled receptor 40 (GPR40). This mechanism is a potential target for new treatments for managing diabetes. In this study, we present the first clinical data for TAK-875, a novel highly selective, orally bioavailable GPR40 agonist, in Japanese patients with type 2 diabetes insufficiently controlled by diet or exercise therapy.
METHODS: This was an exploratory phase II, multicentre, randomized, double-blind, parallel group study comparing the efficacy and tolerability of TAK-875 100 and 400 mg, and placebo, all administered once daily for 2 weeks. RESULTS: After 2 weeks of treatment, TAK-875 produced marked glucose lowering effects in a 75 g oral glucose tolerance test (OGTT) as evidenced by mean ± SE intergroup differences in plasma glucose AUC(0-3 h) of -12.98 ± 1.48 (p < 0.0001) and -8.12 ± 1.49 mmol·h/l (p < 0.0001), for TAK-875 400 mg vs. placebo and TAK-875 100 mg vs. placebo, respectively, and 2 h plasma glucose [-4.95 ± 0.71 (p < 0.0001) and -3.21 ± 0.71 mmol/l (p < 0.0001), respectively]. This was accompanied by a significant increase in insulin AUC(0-3 h) [34.68 ± 12.16 (p < 0.01) and 31.49 ± 12.20 (p < 0 · 05) μIU·h/ml, respectively]. Improvement in glycaemic profile was mirrored by a significant change in fasting plasma glucose [-2.37 ± 0·27 (p < 0.0001) and -1.88 ± 0.27 mmol/l (p < 0.0001), respectively]. No cases of hypoglycaemia were observed despite the significant reduction in plasma glucose.
CONCLUSIONS: These exploratory findings provide evidence of the glucose-dependent insulinotropic potential of the GPR40 agonist TAK-875, and the promising clinical changes support future longer term clinical investigation.
2. ACS Med Chem Lett. 2010 Jun 18;1(6):290-4. doi: 10.1021/ml1000855. eCollection 2010 Sep 9.
Discovery of TAK-875: A Potent, Selective, and Orally Bioavailable GPR40 Agonist.
Negoro N(1), Sasaki S(1), Mikami S(1), Ito M(1), Suzuki M(1), Tsujihata Y(1), Ito R(1), Harada A(1), Takeuchi K(1), Suzuki N(1), Miyazaki J(1), Santou T(1), Odani T(1), Kanzaki N(1), Funami M(1), Tanaka T(1), Kogame A(1), Matsunaga S(1), Yasuma T(1), Momose Y(1).
Author information:
(1)Pharmaceutical Research Division, Takeda Pharmaceutical Company, Ltd., 2-17-85, Jusohonmachi, Yodogawa-ku, Osaka 532-8686, Japan.
GPR40, one of the G protein-coupled receptors predominantly expressed in pancreatic β-cells, mediates enhancement of glucose-stimulated insulin secretion by free fatty acids. A potent and selective GPR40 agonist is theorized to be a safe and effective antidiabetic drug with little or no risk of hypoglycemia. Cyclization of the phenylpropanoic acid moiety of lead compound 1 produced fused phenylalkanoic acids with favorable in vitro agonist activities and pharmacokinetic profiles. Further optimization led to the discovery of dihydrobenzofuran derivative 9a ([(3S)-6-({2/',6/'-dimethyl-4/'-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methoxy)-2, 3-dihydro-1-benzofuran-3-yl]acetic acid hemi-hydrate, TAK-875) as a potent, selective, and orally bioavailable GPR40 agonist, with a pharmacokinetic profile enabling long-acting drug efficacy. Compound 9a showed potent plasma glucose-lowering action and insulinotropic action during an oral glucose tolerance test in female Wistar fatty rats with impaired glucose tolerance. Compound 9a is currently in clinical trials for the treatment of type 2 diabetes mellitus.
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