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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
Structure of SERGLIFLOZIN

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

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:53:15 GMT 2023
Edited
by admin
on Sat Dec 16 08:53:15 GMT 2023
Record UNII
AR34521QFL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SERGLIFLOZIN
WHO-DD  
Common Name English
Sergliflozin [WHO-DD]
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, 2-((4-METHOXYPHENYL)METHYL)PHENYL
Systematic Name English
SERGLIFLOZIN A
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID00189662
Created by admin on Sat Dec 16 08:53:15 GMT 2023 , Edited by admin on Sat Dec 16 08:53:15 GMT 2023
PRIMARY
CAS
360775-96-8
Created by admin on Sat Dec 16 08:53:15 GMT 2023 , Edited by admin on Sat Dec 16 08:53:15 GMT 2023
PRIMARY
SMS_ID
300000042190
Created by admin on Sat Dec 16 08:53:15 GMT 2023 , Edited by admin on Sat Dec 16 08:53:15 GMT 2023
PRIMARY
FDA UNII
AR34521QFL
Created by admin on Sat Dec 16 08:53:15 GMT 2023 , Edited by admin on Sat Dec 16 08:53:15 GMT 2023
PRIMARY
WIKIPEDIA
Sergliflozin
Created by admin on Sat Dec 16 08:53:15 GMT 2023 , Edited by admin on Sat Dec 16 08:53:15 GMT 2023
PRIMARY
PUBCHEM
10177526
Created by admin on Sat Dec 16 08:53:15 GMT 2023 , Edited by admin on Sat Dec 16 08:53:15 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY