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 ;
PubChem CID	9824918;
IUPHAR/BPS	4587;
ChemSpider	21234810 ;
UNII	4HY3523466;
ChEMBL	ChEMBL450044 ;
CompTox Dashboard (EPA)	DTXSID20961265 ;
Chemical and physical data
Formula	C23H28O9
Molar mass	448.468 g·mol−1
3D 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 ; Key:QLXKHBNJTPICNF-UHFFFAOYSA-N ;
	(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.

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[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.

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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