Tofogliflozin

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, the drug is in Phase III clinical trials.[3][4]

Tofogliflozin monohydrate
Clinical data
Other namesCSG452
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
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H28O7
Molar mass404.459 g·mol−1
3D model (JSmol)
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

Chemistry
Anhydrous tofogliflozin

The active moiety or anhydrous form (ChemSpider ID: 28530778, CHEMBL2110731) 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.

See also

References
  1. "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 65" (PDF). World Health Organization. Retrieved 15 November 2016.
  2. Chugai Pharmaceutical: Development Pipeline
  3. 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.
  4. 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.
  5. Statement on a nonproprietary name adopted by the USAN council: Tofogliflozin.
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