Tofogliflozin

Tofogliflozin monohydrate
Clinical data

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)
Synonyms	CSG452
CAS Number	1201913-82-7 903565-83-3 (anhydrous)
PubChem (CID)	46908928
ChemSpider	28527871
KEGG	D09978
ChEMBL	CHEMBL2105711
Chemical and physical data
Formula	C₂₂H₂₈O₇
Molar mass	404.45 g/mol
3D model (Jmol)	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, the drug is in Phase III clinical trials.^[3]^[4]

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.

1 2 "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.; Murao, N.; Yamaguchi, K.; Kato, M.; Mitsui, T.; Suzuki, Y.; Ikeda, S.; Kawabe, Y. (2012). "Selective SGLT2 inhibition by tofogliflozin reduces renal glucose reabsorption under hyperglycemic but not under hypo- or euglycemic conditions in rats". AJP: Endocrinology and Metabolism. 304 (4): E414–E423. doi:10.1152/ajpendo.00545.2012. PMID 23249697.
↑ Ohtake, Y.; Sato, T.; Kobayashi, T.; Nishimoto, M.; Taka, N.; Takano, K.; Yamamoto, K.; Ohmori, M.; Yamaguchi, M.; Takami, K.; Yeu, S. Y.; Ahn, K. H.; Matsuoka, H.; Morikawa, K.; Suzuki, M.; Hagita, H.; Ozawa, K.; Yamaguchi, K.; Kato, M.; Ikeda, S. (2012). "Discovery of Tofogliflozin, a NovelC-Arylglucoside with anO-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): 7828–7840. doi:10.1021/jm300884k. PMID 22889351.
↑ Statement on a nonproprietary name adopted by the USAN council: Tofogliflozin.

Oral anti-diabetic drugs, insulins and insulin analogs, and other drugs used in diabetes (A10)

Biguanides	Buformin^‡ Metformin^# Phenformin^‡

TZDs/"glitazones" (PPAR)	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡

Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§

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

Analogs/other insulins

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§

Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose

Amylin analog	Pramlintide

Sodium glucose transporter (SGLT2) inhibitors/"gliflozins"	Canagliflozin Dapagliflozin Empagliflozin Ipragliflozin Remogliflozin^§ Sergliflozin^§ Tofogliflozin^†

Other	Benfluorex^‡ Bromocriptine

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