Ipragliflozin

Modify Date: 2025-08-20 09:49:03

Ipragliflozin Structure
Ipragliflozin structure
 Common Name Ipragliflozin
CAS Number 761423-87-4 Molecular Weight 404.452
Density 1.5±0.1 g/cm3 Boiling Point 628.8±55.0 °C at 760 mmHg
Molecular Formula C21H21FO5S Melting Point N/A
MSDS N/A Flash Point 334.1±31.5 °C

 Use of Ipragliflozin


Ipragliflozin (ASP1941) is a highly potent and selective SGLT2 inhibitor with IC50 of 2.8 nM; little and NO potency for SGLT1/3/4/5/6.IC50 value: 2.8 nM [1][2]Target: SGLT2in vitro: Ipragliflozin potently and selectively inhibited human, rat, and mouse SGLT2 at nanomolar ranges and exhibited stability against intestinal glucosidases [3].in vivo: Ipragliflozin showed good pharmacokinetic properties following oral dosing, and dose-dependently increased urinary glucose excretion, which lasted for over 12 h in normal mice [3]. Oral administration of ipragliflozin increased urinary glucose excretion in a dose-dependent manner, an effect which was significant at doses of 0.3 mg/kg or higher and lasted over 12 h [4]. Single administration of ipragliflozin dose-dependently increased urinary glucose excretion, reduced blood glucose and plasma insulin levels, and improved glucose intolerance [5].

 Names

Name (2S,3R,4R,5S,6R)-2-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonym More Synonyms

 Ipragliflozin Biological Activity

Description Ipragliflozin (ASP1941) is a highly potent and selective SGLT2 inhibitor with IC50 of 2.8 nM; little and NO potency for SGLT1/3/4/5/6.IC50 value: 2.8 nM [1][2]Target: SGLT2in vitro: Ipragliflozin potently and selectively inhibited human, rat, and mouse SGLT2 at nanomolar ranges and exhibited stability against intestinal glucosidases [3].in vivo: Ipragliflozin showed good pharmacokinetic properties following oral dosing, and dose-dependently increased urinary glucose excretion, which lasted for over 12 h in normal mice [3]. Oral administration of ipragliflozin increased urinary glucose excretion in a dose-dependent manner, an effect which was significant at doses of 0.3 mg/kg or higher and lasted over 12 h [4]. Single administration of ipragliflozin dose-dependently increased urinary glucose excretion, reduced blood glucose and plasma insulin levels, and improved glucose intolerance [5].
Related Catalog
References

[1]. Imamura M, et al. 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. Bioorg Med Chem. 2012 May 15;20(10):3263-79.

[2]. Suzuki M, et al. Tofogliflozin, a potent and highly specific sodium/glucose cotransporter 2 inhibitor, improves glycemic control in diabetic rats and mice. J Pharmacol Exp Ther. 2012 Jun;341(3):692-701.

[3]. Tahara A, et al. Pharmacological profile of ipragliflozin (ASP1941), a novel selective SGLT2 inhibitor, in vitro and in vivo. Naunyn Schmiedebergs Arch Pharmacol. 2012 Apr;385(4):423-36.

[4]. Tahara A, et al. Antidiabetic effects of SGLT2-selective inhibitor ipragliflozin in streptozotocin-nicotinamide-induced mildly diabetic mice. J Pharmacol Sci. 2012;120(1):36-44.

[5]. Tahara A, et al. Effects of SGLT2 selective inhibitor ipragliflozin on hyperglycemia, hyperlipidemia, hepatic steatosis, oxidative stress, inflammation, and obesity in type 2 diabetic mice. Eur J Pharmacol. 2013 Sep 5;715(1-3):246-55.

[6]. Yoshikawa T, et al. Arterial pressure lability is improved by sodium-glucose cotransporter 2 inhibitor in streptozotocin-induced diabetic rats. Hypertens Res. 2017 Jul;40(7):646-651.

[7]. Sakaeda T, et al. Susceptibility to serious skin and subcutaneous tissue disorders and skin tissue distribution of sodium-dependent glucose co-transporter type 2 (SGLT2) inhibitors. Int J Med Sci. 2018 Jun 13;15(9):937-943.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 628.8±55.0 °C at 760 mmHg
Molecular Formula C21H21FO5S
Molecular Weight 404.452
Flash Point 334.1±31.5 °C
Exact Mass 404.109375
PSA 118.39000
LogP 5.59
Vapour Pressure 0.0±1.9 mmHg at 25°C
Index of Refraction 1.684
Storage condition -20℃

 Synthetic Route

(1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl-D-glucitol structure

(1S)-1,5-anhydr...

CAS#:761423-01-2

~88%

Ipragliflozin Structure

Ipragliflozin

CAS#:761423-87-4

Literature: Astellas Pharma Inc.; Kotobuki Pharmaceutical Co., Ltd. Patent: EP2105442 A1, 2009 ; Location in patent: Page/Page column 13 ;
(1S)-1,5-Anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-D-glucitol 2,3,4,6-tetraacetate structure

(1S)-1,5-Anhydr...

CAS#:1034305-21-9

~97%

Ipragliflozin Structure

Ipragliflozin

CAS#:761423-87-4

Literature: Astellas Pharma Inc.; Kotobuki Pharmaceutical Co., Ltd. Patent: EP2105442 A1, 2009 ; Location in patent: Page/Page column 15 ;
Benzo[b]thiophen-2-yl(5-bromo-2-fluorophenyl)methanol structure

Benzo[b]thiophe...

CAS#:1034305-11-7

~%

Ipragliflozin Structure

Ipragliflozin

CAS#:761423-87-4

Literature: Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279
2-(5-Bromo-2-fluorobenzyl)benzothiophene structure

2-(5-Bromo-2-fl...

CAS#:1034305-17-3

~%

Ipragliflozin Structure

Ipragliflozin

CAS#:761423-87-4

Literature: Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279
5-Bromo-2-fluorobenzaldehyde structure

5-Bromo-2-fluor...

CAS#:93777-26-5

~%

Ipragliflozin Structure

Ipragliflozin

CAS#:761423-87-4

Literature: Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279
Thianaphthene structure

Thianaphthene

CAS#:95-15-8

~%

Ipragliflozin Structure

Ipragliflozin

CAS#:761423-87-4

Literature: Bioorganic and Medicinal Chemistry, , vol. 20, # 10 p. 3263 - 3279

 Synonyms

D-Glucitol, 1,5-anhydro-1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-, (1S)-
ASP1941
UNII-3N2N8OOR7X
ASP 1941
(1S)-1,5-Anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-D-glucitol
Suglat
Ipragliflozin
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