IPRAGLIFLOZIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H21FO5S
Molecular Weight	404.452
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C2=CC=C(F)C(CC3=CC4=C(S3)C=CC=C4)=C2

InChI

InChIKey=AHFWIQIYAXSLBA-RQXATKFSSA-N

InChI=1S/C21H21FO5S/c22-15-6-5-12(21-20(26)19(25)18(24)16(10-23)27-21)7-13(15)9-14-8-11-3-1-2-4-17(11)28-14/h1-8,16,18-21,23-26H,9-10H2/t16-,18-,19+,20-,21+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.astellas.com/en/news/10121 | https://www.medscape.com/viewarticle/819447 | https://www.ncbi.nlm.nih.gov/pubmed/25685284 | https://www.ncbi.nlm.nih.gov/pubmed/24668021

Ipragliflozin is an orally active, next-generation sodium glucose transporter-2 (SGLT2) inhibitor that has been developed by Astellas Pharma and Kotobuki. SGLTs are membrane proteins exist on the cell surface and transfer glucose into cells. SGLT2 is one subtype of SGLTs that plays a key role in the reuptake of glucose in the the proximal tubule of the kidneys. By selectively inhibiting SGLT2, Ipragliflozin suppresses the reuptake of glucose and reduces blood glucose levels. Ipragliflozin received marketing approval for the indication of type 2 diabetes under the brand name Suglat® Tablets in January 2014 and has been on the market since April 2014.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 2 25 Target ID: CHEMBL3884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22507206	Inhibitor 8297		7.38 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259

PubMed

Title	Date	PubMed
Safety, pharmacokinetic, and pharmacodynamic profiles of ipragliflozin (ASP1941), a novel and selective inhibitor of sodium-dependent glucose co-transporter 2, in patients with type 2 diabetes mellitus.	2011 Dec	21854192
Efficacy and safety of ipragliflozin in patients with type 2 diabetes inadequately controlled on metformin: a dose-finding study.	2013 May	23163880
Inhibition of the sodium glucose co-transporter-2: its beneficial action and potential combination therapy for type 2 diabetes mellitus.	2013 May	23331516
Active- and placebo-controlled dose-finding study to assess the efficacy, safety, and tolerability of multiple doses of ipragliflozin in patients with type 2 diabetes mellitus.	2013 May-Jun	23276620

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage is 50 mg of ipragliflozin orally administered once daily before or after breakfast. The dose may be increased up to 100 mg once daily with careful monitoring of the patient’s clinical course in the case of inadequate efficacy.

Route of Administration: Oral

Name

Type

Language

IPRAGLIFLOZIN

Official Name

English

D-GLUCITOL, 1,5-ANHYDRO-1-C-(3-(BENZO(B)THIEN-2-YLMETHYL)-4-FLUOROPHENYL)-, (1S)-

Common Name

English

ASP-1941

Code

English

ipragliflozin [INN]

Common Name

English

(1S)-1,5-ANHYDRO-1-C-(3-((1-BENZOTHIOPHEN-2-YL)METHYL)-4-FLUOROPHENYL)-D-GLUCITOL

Common Name

English

IPRAGLIFLOZIN [MI]

Common Name

English

Ipragliflozin [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

A10BK05