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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 of IPRAGLIFLOZIN L-PROLINE

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

Description

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

Unknown
127998
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8146
 7.38 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
SUGLAT

Approved Use

Ipragliflozin L-proline is indicated for the treatment of type 2 diabetes.

Launch Date

1.38983034E12
PubMed

PubMed

TitleDatePubMed
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
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
Patents

Patents

US-7202350-B2
1

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.
Name Type Language
IPRAGLIFLOZIN L-PROLINE
JAN   WHO-DD  
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
Created by admin on Sat Dec 17 03:42:45 UTC 2022 , Edited by admin on Sat Dec 17 03:42:45 UTC 2022
PRIMARY
MERCK INDEX
M11865
Created by admin on Sat Dec 17 03:42:45 UTC 2022 , Edited by admin on Sat Dec 17 03:42:45 UTC 2022
PRIMARY
FDA UNII
M6N3GK48A4
Created by admin on Sat Dec 17 03:42:45 UTC 2022 , Edited by admin on Sat Dec 17 03:42:45 UTC 2022
PRIMARY
CAS
951382-34-6
Created by admin on Sat Dec 17 03:42:45 UTC 2022 , Edited by admin on Sat Dec 17 03:42:45 UTC 2022
PRIMARY
EVMPD
SUB180798
Created by admin on Sat Dec 17 03:42:45 UTC 2022 , Edited by admin on Sat Dec 17 03:42:45 UTC 2022
PRIMARY
PUBCHEM
57339444
Created by admin on Sat Dec 17 03:42:45 UTC 2022 , Edited by admin on Sat Dec 17 03:42:45 UTC 2022
PRIMARY
PARENT (SALT/SOLVATE)
Structure of IPRAGLIFLOZIN
PARENT (SALT/SOLVATE)
Structure of PROLINE
NIH
NCATS
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