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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H28O9
Molecular Weight 448.463
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SERGLIFLOZIN ETABONATE

SMILES

CCOC(=O)OC[C@H]1O[C@@H](OC2=C(CC3=CC=C(OC)C=C3)C=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=QLXKHBNJTPICNF-QMCAAQAGSA-N
InChI=1S/C23H28O9/c1-3-29-23(27)30-13-18-19(24)20(25)21(26)22(32-18)31-17-7-5-4-6-15(17)12-14-8-10-16(28-2)11-9-14/h4-11,18-22,24-26H,3,12-13H2,1-2H3/t18-,19-,20+,21-,22-/m1/s1

HIDE SMILES / InChI
Sergliflozin, a novel oral selective low-affinity sodium glucose cotransporter (SGLT2) inhibitor, improves hyperglycemia by suppressing renal glucose reabsorption, in which SGLT2 participates as a dominant transporter. Its prodrug form, sergliflozin etabonate, is orally available and is converted to sergiflozin upon absorption. Development of sergliflozin has been discontinued in favor of remogliflozin.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

A phase I study with 50–500 mg of sergliflozin in 14 healthy volunteers and a phase IIa study where the same dose range was given to eight subjects with T2DM showed a dose-dependent increase in urinary glucose excretion that plateaued at higher doses. It did not cause hypoglycemia in nondiabetic subjects, and there was a 1.5-kg weight loss from baseline to d 15 compared with placebo.
Route of Administration: Oral
The Ki values for sergliflozin, sergliflozin-A toward human SGLT2 are 151 nM and 2.39 nM, resp.
Name Type Language
SERGLIFLOZIN ETABONATE
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
sergliflozin etabonate [INN]
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, 2-((4-METHOXYPHENYL)METHYL)PHENYL 6-O-(ETHOXYCARBONYL)-
Common Name English
GW-869683X
Code English
GW-869682X
Code English
SERGLIFLOZIN ETABONATE [USAN]
Common Name English
GW869682X
Code English
Sergliflozin etabonate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98083
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
Code System Code Type Description
USAN
RR-47
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
PRIMARY
NCI_THESAURUS
C78129
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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WIKIPEDIA
SERGLIFLOZIN ETABONATE
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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FDA UNII
4HY3523466
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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MESH
C516973
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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CAS
408504-26-7
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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INN
8790
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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MESH
C546025
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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PUBCHEM
9824918
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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ChEMBL
CHEMBL450044
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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SMS_ID
300000034388
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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EPA CompTox
DTXSID20961265
Created by admin on Fri Dec 15 16:01:57 GMT 2023 , Edited by admin on Fri Dec 15 16:01:57 GMT 2023
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