CAS 761423-87-4|Ipragliflozin

Introduction：Basic information about CAS 761423-87-4|Ipragliflozin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Ipragliflozin BiologicalActivity
3. Chemical & Physical Properties
4. Synonyms

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	/
MSDS	/	Flash Point	334.1±31.5 °C

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 BiologicalActivity

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	Signaling Pathways >>Membrane Transporter/Ion Channel >>SGLTResearch Areas >>Metabolic Disease
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.

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

Signaling Pathways >>Membrane Transporter/Ion Channel >>SGLTResearch Areas >>Metabolic Disease

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
InChIKey	AHFWIQIYAXSLBA-RQXATKFSSA-N
SMILES	OCC1OC(c2ccc(F)c(Cc3cc4ccccc4s3)c2)C(O)C(O)C1O
Storage condition	-20℃

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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