Tofogliflozin

Tofogliflozin monohydrate
Clinical data
Other names	CSG452
ATC code	None;
Legal status
Legal status	Investigational;
Identifiers
	IUPAC name (1S,3'R,4'S,5'S,6'R)-6-(4-Ethylbenzyl)-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-3H-spiro[2-benzofuran-1,2'-pyran]-3',4',5'-triol hydrate (1:1);
CAS Number	1201913-82-7 ; 903565-83-3 (anhydrous);
PubChem CID	46908928;
ChemSpider	28527871;
UNII	P8DD8KX4O4;
KEGG	D09978;
ChEMBL	ChEMBL2105711;
CompTox Dashboard (EPA)	DTXSID70152722 ;
Chemical and physical data
Formula	C22H28O7
Molar mass	404.459 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCc1ccc(cc1)Cc2ccc3c(c2)[C@]4([C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC3.O;
	InChI InChI=1S/C22H26O6.H2O/c1-2-13-3-5-14(6-4-13)9-15-7-8-16-12-27-22(17(16)10-15)21(26)20(25)19(24)18(11-23)28-22;/h3-8,10,18-21,23-26H,2,9,11-12H2,1H3;1H2/t18-,19-,20+,21-,22+;/m1./s1; Key:ZXOCGDDVNPDRIW-NHFZGCSJSA-N;

Tofogliflozin (INN,^[1]^: 88 USAN, codenamed CSG452) is an experimental drug for the treatment of diabetes mellitus and is being developed by Chugai Pharma in collaboration with Kowa and Sanofi.^[2] It is an inhibitor of subtype 2 sodium-glucose transport protein (SGLT2), which is responsible for at least 90% of the glucose reabsorption in the kidney. As of September 2012^[update], the drug is in Phase III clinical trials.^[3]^[4]^{[needs update]}

Chemistry

Anhydrous tofogliflozin

The active moiety or anhydrous form (ChemSpider ID: 28530778, CHEMBL 2110731) has the chemical formula C₂₂H₂₆O₆ and a molecular mass of 386.44 g/mol.

The United States Adopted Name tofogliflozin applies to the monohydrate, which is the form used as a drug.^[5] The International Nonproprietary Name tofogliflozin applies to the anhydrous compound^[1] and the drug form is referred to as tofogliflozin hydrate.

^ ^a ^b "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 65" (PDF). World Health Organization. Retrieved 15 November 2016.
^ Chugai Pharmaceutical: Development Pipeline
^ Nagata T, Fukazawa M, Honda K, Yata T, Kawai M, Yamane M, et al. (February 2013). "Selective SGLT2 inhibition by tofogliflozin reduces renal glucose reabsorption under hyperglycemic but not under hypo- or euglycemic conditions in rats". American Journal of Physiology. Endocrinology and Metabolism. 304 (4): E414-23. doi:10.1152/ajpendo.00545.2012. PMID 23249697.
^ Ohtake Y, Sato T, Kobayashi T, Nishimoto M, Taka N, Takano K, et al. (September 2012). "Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes". Journal of Medicinal Chemistry. 55 (17): 7828–40. doi:10.1021/jm300884k. PMID 22889351.
^ Statement on a nonproprietary name adopted by the USAN council: Tofogliflozin.

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