Literature DB >> 22507206

Discovery of Ipragliflozin (ASP1941): a novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus.

Masakazu Imamura1, Keita Nakanishi, Takayuki Suzuki, Kazuhiro Ikegai, Ryota Shiraki, Takashi Ogiyama, Takeshi Murakami, Eiji Kurosaki, Atsushi Noda, Yoshinori Kobayashi, Masayuki Yokota, Tomokazu Koide, Kazuhiro Kosakai, Yasufumi Ohkura, Makoto Takeuchi, Hiroshi Tomiyama, Mitsuaki Ohta.   

Abstract

A series of C-glucosides with various heteroaromatics has been synthesized and its inhibitory activity toward SGLTs was evaluated. Upon screening several compounds, the benzothiophene derivative (14a) was found to have potent inhibitory activity against SGLT2 and good selectivity versus SGLT1. Through further optimization of 14a, a novel benzothiophene derivative (14h; ipragliflozin, ASP1941) was discovered as a highly potent and selective SGLT2 inhibitor that reduced blood glucose levels in a dose-dependent manner in diabetic models KK-A(y) mice and STZ rats.
Copyright © 2012 Elsevier Ltd. All rights reserved.

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Year:  2012        PMID： 22507206     DOI： 10.1016/j.bmc.2012.03.051

Source DB:  PubMed          Journal:  Bioorg Med Chem        ISSN： 0968-0896            Impact factor:   3.641


  11 in total

Review 1.  Clinical pharmacokinetics and pharmacodynamics of the novel SGLT2 inhibitor ipragliflozin.

Authors:  Takeshi Kadokura; Wenhui Zhang; Walter Krauwinkel; Stefanie Leeflang; James Keirns; Yuta Taniuchi; Ikumi Nakajo; Ronald Smulders
Journal:  Clin Pharmacokinet       Date:  2014-11       Impact factor: 6.447

2.  What does sodium-glucose co-transporter 1 inhibition add: Prospects for dual inhibition.

Authors:  Jessica A Dominguez Rieg; Timo Rieg
Journal:  Diabetes Obes Metab       Date:  2019-04       Impact factor: 6.577

3.  Ipragliflozin: first global approval.

Authors:  Raewyn M Poole; Rosselle T Dungo
Journal:  Drugs       Date:  2014-04       Impact factor: 9.546

4.  Functional imaging of pharmacological action of SGLT2 inhibitor ipragliflozin via PET imaging using 11C-MDG.

Authors:  Keisuke Mitsuoka; Yuka Hayashizaki; Yoshihiro Murakami; Toshiyuki Takasu; Masanori Yokono; Nobuhiro Umeda; Shoji Takakura; Akihiro Noda; Sosuke Miyoshi
Journal:  Pharmacol Res Perspect       Date:  2016-07-01

5.  A concise and practical stereoselective synthesis of ipragliflozin L-proline.

Authors:  Shuai Ma; Zhenren Liu; Jing Pan; Shunli Zhang; Weicheng Zhou
Journal:  Beilstein J Org Chem       Date:  2017-06-01       Impact factor: 2.883

Review 6.  The modification of natural products for medical use.

Authors:  Zongru Guo
Journal:  Acta Pharm Sin B       Date:  2016-11-25       Impact factor: 11.413

7.  Preventive effects of the sodium glucose cotransporter 2 inhibitor tofogliflozin on diethylnitrosamine-induced liver tumorigenesis in obese and diabetic mice.

Authors:  Koki Obara; Yohei Shirakami; Akinori Maruta; Takayasu Ideta; Tsuneyuki Miyazaki; Takahiro Kochi; Hiroyasu Sakai; Takuji Tanaka; Mitsuru Seishima; Masahito Shimizu
Journal:  Oncotarget       Date:  2017-04-06

Review 8.  New Aspects of Diabetes Research and Therapeutic Development.

Authors:  Leslie S Satin; Scott A Soleimanpour; Emily M Walker
Journal:  Pharmacol Rev       Date:  2021-07       Impact factor: 18.923

9.  The Selective SGLT2 Inhibitor Ipragliflozin Has a Therapeutic Effect on Nonalcoholic Steatohepatitis in Mice.

Authors:  Yasushi Honda; Kento Imajo; Takayuki Kato; Takaomi Kessoku; Yuji Ogawa; Wataru Tomeno; Shingo Kato; Hironori Mawatari; Koji Fujita; Masato Yoneda; Satoru Saito; Atsushi Nakajima
Journal:  PLoS One       Date:  2016-01-05       Impact factor: 3.240

Review 10.  Profile of Ipragliflozin, an Oral SGLT-2 Inhibitor for the Treatment of Type 2 Diabetes: The Evidence to Date.

Authors:  Wajd Alkabbani; John-Michael Gamble
Journal:  Drug Des Devel Ther       Date:  2021-07-14       Impact factor: 4.162
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