Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H24O7 |
| Molecular Weight | 376.4004 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(CC2=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=CC=C2)C=C1
InChI
InChIKey=HFLCZNNDZKKXCS-OUUBHVDSSA-N
InChI=1S/C20H24O7/c1-25-14-8-6-12(7-9-14)10-13-4-2-3-5-15(13)26-20-19(24)18(23)17(22)16(11-21)27-20/h2-9,16-24H,10-11H2,1H3/t16-,17-,18+,19-,20-/m1/s1
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 |
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| 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 |
|
| 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 |
|
| 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 |
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
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DTXSID00189662
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360775-96-8
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Sergliflozin
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10177526
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
