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Sergliflozin etabonate

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Chemical compound Pharmaceutical compound
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
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
  • Key:QLXKHBNJTPICNF-UHFFFAOYSA-N
  (what is this?)  (verify)

Sergliflozin etabonate (INN/USAN, 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.

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". Archived from the original on 2007-11-05. Retrieved 2008-10-28.
Oral diabetes medication, insulins and insulin analogs, and other drugs used in diabetes (A10)
Insulins / insulin analogs
fast-acting
short-acting
long-acting
ultra-long-acting
inhalable
  • Exubera
  • Afrezza
Non-insulins
Insulin sensitizers
Biguanides
TZDs/"glitazones" (PPAR)
Dual PPAR agonists
Amylin analogs and DACRAs
Secretagogues
KATP
Sulfonylureas
Meglitinides/"glinides"
GLP-1 receptor agonists
GLP1 poly-agonist peptides
DPP-4 inhibitors/"gliptins"
Other
Aldose reductase inhibitors
Alpha-glucosidase inhibitors
SGLT2 inhibitors/"gliflozins"
Other
Combinations
Sodium-glucose transporter modulators
SGLT1Tooltip Sodium-glucose transporter 1
SGLT2Tooltip Sodium-glucose transporter 2
SGLT1Tooltip Sodium-glucose transporter 1 & SGLT2Tooltip Sodium-glucose transporter 2
See also: Receptor/signaling modulators


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