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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 of IPRAGLIFLOZIN

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
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

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 7.38 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Antidiabetic effects of SGLT2-selective inhibitor ipragliflozin in streptozotocin-nicotinamide-induced mildly diabetic mice.
2012
No pharmacokinetic interaction between ipragliflozin and sitagliptin, pioglitazone, or glimepiride in healthy subjects.
2012 Oct
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
Patents

Patents

08097592
1
08198464
1
20060122126
1
20070161787
1
20090069252
1
20090143316
1
20100094025
1
JP5302900B2
5
US7202350
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:56:56 UTC 2023
Edited
by admin
on Sat Dec 16 17:56:56 UTC 2023
Record UNII
3N2N8OOR7X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IPRAGLIFLOZIN
INN   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
Code System Code Type Description
CAS
761423-87-4
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
MESH
C572941
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
PUBCHEM
10453870
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
DRUG BANK
DB11698
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
NCI_THESAURUS
C166685
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
EPA CompTox
DTXSID701032738
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
SMS_ID
100000128632
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
WIKIPEDIA
Ipragliflozin
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
DRUG CENTRAL
4890
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
EVMPD
SUB35918
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
FDA UNII
3N2N8OOR7X
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
INN
9258
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
MERCK INDEX
m11865
Created by admin on Sat Dec 16 17:56:57 UTC 2023 , Edited by admin on Sat Dec 16 17:56:57 UTC 2023
PRIMARY
Related Record Type Details
SODIUM/GLUCOSE COTRANSPORTER 2
TARGET -> INHIBITOR
Structure of IPRAGLIFLOZIN L-PROLINE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of IPRAGLIFLOZIN
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