Sergliflozin etabonate

Chemical compound

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

UNII

4HY3523466

ChEMBL

ChEMBL450044^N

CompTox Dashboard (EPA)

DTXSID20961265

Chemical and physical dataFormulaC₂₃H₂₈O₉Molar mass448.468 g·mol⁻¹3D model (JSmol)

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.^{[citation needed]}

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.

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. Archived from the original (PDF) on February 19, 2009.
^ "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. S2CID 8306408.
^ "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	Insulin aspart Insulin glulisine Insulin lispro
short-acting	Regular insulin^#
long-acting	Insulin detemir^# Insulin glargine^# (+lixisenatide) NPH insulin Lente insulin^‡ Ultralente insulin^‡
ultra-long-acting	Insulin degludec^# (+insulin aspart, +liraglutide) Insulin icodec^† (+semaglutide)
inhalable	Exubera^‡ Afrezza

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^‡Withdrawn from market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

Non-insulins

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^§
Amylin analogs and DACRAs	Cagrilintide^§ Pramlintide

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 receptor agonists

GLP1 poly-agonist peptides	Mazdutide (GLP-1/GCGR) Retatrutide^§ (GLP-1/GIP/GCGR) Tirzepatide (GLP-1/GIP)

DPP-4 inhibitors/"gliptins"

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§
Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose
SGLT2 inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin^# Ertugliflozin Ipragliflozin Luseogliflozin Remogliflozin^§ Sergliflozin^§ Sotagliflozin Tofogliflozin^† Velagliflozin
Other	Benfluorex^‡ Bromocriptine Imeglimin

Combinations

Alogliptin/metformin
Canagliflozin/metformin
Cagrilintide/semaglutide^§
Dapagliflozin/metformin
Dapagliflozin/saxagliptin
Dapagliflozin/saxagliptin/metformin
Empagliflozin/linagliptin
Empagliflozin/metformin
Gemigliptin/rosuvastatin
Glibenclamide (glyburide)/metformin
Glimepiride/rosiglitazone
Linagliptin/metformin
Metformin/acarbose
Metformin/ertugliflozin
Metformin/evogliptin
Metformin/gemigliptin
Metformin/repaglinide
Metformin/sulfonylureas
Metformin/teneligliptin
Phenformin/sulfonylureas
Pioglitazone/alogliptin
Pioglitazone/glimepiride
Pioglitazone/metformin
Pioglitazone/sitagliptin
Rosiglitazone/metformin
Saxagliptin/metformin
Sitagliptin/dapagliflozin
Sitagliptin/ertugliflozin
Sitagliptin/metformin
Sitagliptin/simvastatin
Vildagliptin/metformin

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

v t e Sodium-glucose transporter modulators
SGLT1Tooltip Sodium-glucose transporter 1	Inhibitors: Phloretin Phlorizin T-1095 T-1095A
SGLT2Tooltip Sodium-glucose transporter 2	Inhibitors: Atigliflozin Bexagliflozin Canagliflozin Dapagliflozin Empagliflozin Enavogliflozin Ertugliflozin Henagliflozin Ipragliflozin Janagliflozin Licogliflozin Luseogliflozin Mizagliflozin Phloretin Phlorizin Remogliflozin Sergliflozin T-1095 T-1095A Tofogliflozin Velagliflozin Antisense oligonucleotides: ISIS-388626
SGLT1Tooltip Sodium-glucose transporter 1 & SGLT2Tooltip Sodium-glucose transporter 2	Inhibitors: Sotagliflozin
See also: Receptor/signaling modulators