SERGLIFLOZIN ETABONATE

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 Search

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

Molecular Formula	C23H28O9
Molecular Weight	448.463
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/17050778 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C78129 | https://www.ncbi.nlm.nih.gov/pubmed/20056803

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.

Originator

Approval Year

PubMed

Title	Date	PubMed
Sergliflozin, a novel selective inhibitor of low-affinity sodium glucose cotransporter (SGLT2), validates the critical role of SGLT2 in renal glucose reabsorption and modulates plasma glucose level.	2007 Jan	17050778
Single-dose pharmacokinetics and pharmacodynamics of sergliflozin etabonate, a novel inhibitor of glucose reabsorption, in healthy volunteers and patients with type 2 diabetes mellitus.	2010 Jun	20056803
Discovery of a clinical candidate from the structurally unique dioxa-bicyclo[3.2.1]octane class of sodium-dependent glucose cotransporter 2 inhibitors.	2011 Apr 28	21449606
Discovery of novel N-β-D-xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes.	2011 Jan 13	21128592

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

The Ki values for sergliflozin, sergliflozin-A toward human SGLT2 are 151 nM and 2.39 nM, resp.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:01:57 UTC 2023` Edited by `admin` on `Fri Dec 15 16:01:57 UTC 2023`
Record UNII	4HY3523466
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SERGLIFLOZIN ETABONATE

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