Tofogliflozin

Tofogliflozin monohydrate

Systematic (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)
Clinical data
Legal status	Investigational
Identifiers
CAS Number	1201913-82-7 Template:CAS (anhydrous)
ATC code	None
PubChem	CID: 46908928
ChemSpider	28527871
KEGG	D09978
ChEMBL	CHEMBL2105711
Synonyms	CSG452
Chemical data
Formula	C22H28O7
Molecular mass	404.45 g/mol
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 (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. 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, the drug is in Phase III clinical trials.

Chemistry

Tofogliflozin is the name of the monohydrate, which is the form used as a drug. The active moiety or anhydrous form (ChemSpider ID: 28530778, CHEMBL2110731) has the chemical formula C₂₂H₂₆O₆ and a molecular mass of 386.44 g/mol.