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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

Description

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

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.