Sergliflozin etabonate

Sergliflozin etabonate
Clinical data
Routes of
administration		Oral
ATC code
  • none
Identifiers
IUPAC name
  • 2-(4-methoxybenzyl)phenyl 6-O-(ethoxycarbonyl)-β-D-glucopyranoside
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H28O9
Molar mass448.468 g·mol−1
3D model (JSmol)
SMILES
  • CCOC(=O)OCC1C(C(C(C(O1)Oc2ccccc2Cc3ccc(cc3)OC)O)O)O
InChI
  • 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 ☒N
  • Key:QLXKHBNJTPICNF-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Sergliflozin etabonate (INN/USAN,[1][2] codenamed GW869682X) is an investigational anti-diabetic drug being developed by GlaxoSmithKline. It did not undergo further development after phase II.

Method of action

Sergliflozin inhibits subtype 2 of the sodium-glucose transport proteins (SGLT2), which is responsible for at least 90% of the glucose reabsorption in the kidney. Blocking this transporter causes blood glucose to be eliminated through the urine.[3][4]

Chemistry

Etabonate refers to the ethyl carbonate group. The remaining structure, which is the active substance, is called sergliflozin.

Sergliflozin

References

  1. ↑ World Health Organization (2008). "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 59" (PDF). WHO Drug Information. 22 (1): 66. Archived from the original (PDF) on February 19, 2009.
  2. ↑ "Statement on a nonproprietary name adopted by the USAN council: Sergliflozin etabonate" (PDF). American Medical Association. Retrieved 2008-08-10.
  3. ↑ Katsuno K, Fujimori Y, Takemura Y, et al. (January 2007). "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". J Pharmacol Exp Ther. 320 (1): 323–30. doi:10.1124/jpet.106.110296. PMID 17050778. S2CID 8306408.
  4. ↑ Prous Science: Molecule of the Month November 2007


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