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
Molecular Formula | C20H24O7 |
Molecular Weight | 376.4004 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
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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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19892839
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17050778
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
Edited
Sat Dec 16 08:53:15 GMT 2023
by
admin
on
Sat Dec 16 08:53:15 GMT 2023
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Record UNII |
AR34521QFL
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Record Status |
Validated (UNII)
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Record Version |
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-
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DTXSID00189662
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360775-96-8
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300000042190
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AR34521QFL
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Sergliflozin
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10177526
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |