REMOGLIFLOZIN ETABONATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H38N2O9
Molecular Weight	522.5879
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)OC[C@H]1O[C@@H](OC2=NN(C(C)C)C(C)=C2CC3=CC=C(OC(C)C)C=C3)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=UAOCLDQAQNNEAX-ABMICEGHSA-N

InChI=1S/C26H38N2O9/c1-7-33-26(32)34-13-20-21(29)22(30)23(31)25(36-20)37-24-19(16(6)28(27-24)14(2)3)12-17-8-10-18(11-9-17)35-15(4)5/h8-11,14-15,20-23,25,29-31H,7,12-13H2,1-6H3/t20-,21-,22+,23-,25+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C26H38N2O9
Molecular Weight	522.5879
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26628836

Remogliflozin is the active component of the pro-drug remogliflozin etabonate, which is used the treatment of non-alcoholic steatohepatitis ("NASH") and type 2 diabetes. Remogliflozin inhibits the sodium-glucose transport proteins (SGLT), is selective for SGLT2, which is responsible for glucose reabsorption in the kidney. Blocking this transporter causes blood glucose to be eliminated through the urine.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 2 25 Target ID: P31639 Gene ID: 6524.0 Gene Symbol: SLC5A2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26288025	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Remogliflozin etabonate: a novel SGLT2 inhibitor for treatment of diabetes mellitus.	2015	26288025
Remogliflozin etabonate : a novel SGLT2 inhibitor for treatment of diabetes mellitus.	2015 Aug 14	26271274
Remogliflozin Etabonate Improves Fatty Liver Disease in Diet-Induced Obese Male Mice.	2015 Sep	26628836

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Remogliflozin is the active component of the pro-drug remogliflozin etabonate. Using the ORAC assay, it was determined the antioxidant capacity of equal concentrations of remogliflozin etabonate, remogliflozin, canagliflozin and dapagliflozin. It was shown, remogliflozin displayed a robust antioxidant activity compared to the pro-drug and other SGLT2 inhibitors, canagliflozin and dapagliflozin.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:46 GMT 2023` Edited by `admin` on `Fri Dec 15 15:25:46 GMT 2023`
Record UNII	TR0QT6QSUL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

REMOGLIFLOZIN ETABONATE

Official Name

English

GSK189075A

Code

English

ethyl (((2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1H-pyrazol-3-yl)oxy)tetrahydro-2H-pyran-2-yl)methyl) carbonate

Systematic Name

English

Remogliflozin etabonate [WHO-DD]

Common Name

English

β-D-Glucopyranoside, 5-methyl-4-[[4-(1-methylethoxy)phenyl]methyl]-1-(1-methylethyl)-1H-pyrazol-3-yl, 6-(ethyl carbonate)

Systematic Name

English

GSK-189075

Code

English

GSK-189075A

Code

English

5-METHYL-4-(4-(1-METHYLETHOXY)BENZYL)-1-(1-METHYLETHYL)-1H-PYRAZOL-3-YL 6-O- (ETHOXYCARBONYL)-.BETA.-D-GLUCOPYRANOSIDE

Systematic Name

English

REMOGLIFLOZIN ETABONATE [USAN]

Common Name

English

BHV-091009

Code

English

5-METHYL-1-(PROPAN-2-YL)-4-((4-((PROPAN-2-YL)OXY)PHENYL)METHYL)-1H-PYRAZOL-3-YL 6-O-(ETHOXYCARBONYL)-.BETA.-D-GLUCOPYRANOSIDE

Systematic Name

English

GSK189075

Code

English

remogliflozin etabonate [INN]

Common Name

English

Code System Code Type Description

WIKIPEDIA

REMOGLIFLOZIN ETABONATE