Sergliflozin etabonate

Last updated
Sergliflozin etabonate
Sergliflozin etabonate 2.svg
Clinical data
Routes of
administration
Oral
ATC code
  • none
Identifiers
  • 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
Formula C23H28O9
Molar mass 448.468 g·mol−1
3D model (JSmol)
  • CCOC(=O)OCC1C(C(C(C(O1)Oc2ccccc2Cc3ccc(cc3)OC)O)O)O
  • 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 X mark.svgN
  • Key:QLXKHBNJTPICNF-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (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.[ citation needed ]

Contents

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 Sergliflozin skeletal.svg
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". Archived from the original on 2007-11-05. Retrieved 2008-10-28.