IPRAGLIFLOZIN L-PROLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H21FO5S.C5H9NO2
Molecular Weight	519.582
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@@H]1CCCN1.OC[C@H]2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C3=CC=C(F)C(CC4=CC5=C(S4)C=CC=C5)=C3

InChI

InChIKey=TUVGWWULBZIUBS-FVYIYGEMSA-N

InChI=1S/C21H21FO5S.C5H9NO2/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;7-5(8)4-2-1-3-6-4/h1-8,16,18-21,23-26H,9-10H2;4,6H,1-3H2,(H,7,8)/t16-,18-,19+,20-,21+;4-/m10/s1

HIDE SMILES / InChI

Molecular Formula	C5H9NO2
Molecular Weight	115.1305
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C21H21FO5S
Molecular Weight	404.452
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.pharmacodia.com/yaodu/html/v1/chemicals/8a56257ea05c74018291954fc56fc448.html

Ipragliflozin L-proline is a sodium-glucose cotransporter 2 (SGLT2) inhibitor. It was developed and marketed as Suglat® by Astellas cooperating with Kotobuki Pharmaceutical and Merck Sharp & Dohme, and approved by Pharmaceuticals and Medical Devices Agency of Japan (PMDA) on Jan 17, 2014. It is indicated for the treatment of type 2 diabetes.

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 Sources: https://www.pmda.go.jp/files/000206796.pdf	Primary		Approved 8429	SUGLAT Approved Use Ipragliflozin L-proline is indicated for the treatment of type 2 diabetes. Launch Date 2014

PubMed

Title	Date	PubMed
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.	2012 May 15	22507206
Efficacy, safety, and tolerability of ipragliflozin in Asian patients with type 2 diabetes mellitus and inadequate glycemic control with metformin: Results of a phase 3 randomized, placebo-controlled, double-blind, multicenter trial.	2016 May	27330723

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

In Vitro Use Guide

The inhibitory effect of ipragliflozin on SGLT2 and SGLT1 as measured by sodiumdependent 14C-methyl-α-D-glucopyranoside (14C-AMG) uptake was evaluated in human SGLT2- or SGLT1-expressing CHO cells. As a result, IC50 values were 7.38 and 1880 nmol/L, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:47:56 GMT 2023` Edited by `admin` on `Fri Dec 15 19:47:56 GMT 2023`
Record UNII	M6N3GK48A4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IPRAGLIFLOZIN L-PROLINE

Common Name

English

IPRAGLIFLOZIN L-PROLINE [JAN]

Common Name

English

Ipragliflozin l-proline [WHO-DD]

Common Name

English

L-PROLINE, COMPD. WITH (1S)-1,5-ANHYDRO-1-C-(3-(BENZO(B)THIEN-2-YLMETHYL)-4-FLUOROPHENYL)-D-GLUCITOL (1:1)

Common Name

English

IPRAGLIFLOZIN L-PROLINE [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID20241771