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	408504-26-7^Y
PubChem (CID)	9824918
IUPHAR/BPS	4587
ChemSpider	21234810^N
ChEMBL	CHEMBL450044^N
Chemical and physical data
Formula	C₂₃H₂₈O₉
Molar mass	448.463 g/mol
3D model (Jmol)	Interactive image
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
^NY (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

↑ World Health Organization (2008). "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 59" (PDF). WHO Drug Information. 22 (1): 66.
↑ "Statement on a nonproprietary name adopted by the USAN council: Sergliflozin etabonate" (PDF). American Medical Association. Retrieved 2008-08-10.
↑ 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.
↑ Prous Science: Molecule of the Month November 2007

Oral anti-diabetic drugs, insulins and insulin analogs, and other drugs used in diabetes (A10)

Insulin

Sensitizers

Biguanides	Buformin^‡ Metformin^# Phenformin^‡

TZDs/"glitazones" (PPAR)	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡

Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§

Secretagogues

K⁺_ATP

Sulfonylureas	1st generation: Acetohexamide Carbutamide Chlorpropamide Glycyclamide Metahexamide Tolazamide Tolbutamide 2nd generation: Glibenclamide (glyburide)^# Glibornuride Glicaramide Gliclazide Glimepiride Glipizide Gliquidone Glisoxepide Glyclopyramide

Meglitinides/"glinides"	Mitiglinide Nateglinide Repaglinide

GLP-1 agonists

DPP-4 inhibitors/"gliptins"

Free fatty acid receptor 1 (GPR40)

Fasiglifam^†

Analogs/other insulins

fast-acting (Insulin aspart
Insulin glulisine
Insulin lispro)
short-acting (Regular insulin)
long-acting (Insulin detemir
Insulin glargine
NPH insulin)
ultra-long-acting (Insulin degludec)
inhalable (Exubera^‡
Afrezza)

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

Sodium glucose transporter (SGLT2) inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin Ipragliflozin Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Benfluorex^‡ Bromocriptine

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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