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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 of REMOGLIFLOZIN ETABONATE

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
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P31639
Gene ID: 6524.0
Gene Symbol: SLC5A2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

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

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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.
Name Type Language
REMOGLIFLOZIN ETABONATE
INN   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 15:25:46 GMT 2023 , Edited by admin on Fri Dec 15 15:25:46 GMT 2023
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PUBCHEM
9871420
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EPA CompTox
DTXSID50963191
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MESH
C532127
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INN
8927
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USAN
SS-48
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FDA UNII
TR0QT6QSUL
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DRUG BANK
DB12935
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SMS_ID
300000034370
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NCI_THESAURUS
C91023
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CAS
442201-24-3
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ChEMBL
CHEMBL2028665
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