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Tofogliflozin

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Chemical compound

Pharmaceutical compound

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)
PubChemCID	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]^: 88USAN, codenamedCSG452) is a drug developed for the treatment ofdiabetes mellitus type 2 and was originally co-developed byChugai Pharma in collaboration withKowa andSanofi.^[2] It is an inhibitor of subtype 2sodium-glucose transport protein (SGLT2), which is responsible for at least 90% of the glucosereabsorption in the kidney. As of 2014, tofogliflozin was approved for use inJapan and is marketed under the brand namesApleway andDeberza.^[3]^[4] It has not been approved for use outside of Japan.^[5]

References

[edit]

^"International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 65"(PDF). World Health Organization. Retrieved15 November 2016.
^Chugai Pharmaceutical: Development Pipeline
^Yabe D, Iwasaki M, Kuwata H, Kurose T, Harashima S, Hamasaki A, Seino Y (March 2021)."Efficacy and safety of tofogliflozin in Japanese patients with type 2 diabetes mellitus: A pooled analysis of phase 3 trials".Journal of Diabetes Investigation.12 (3):431–441.doi:10.1111/jdi.13379.PMC 8015831.PMID 33176360.
^"Drugs Approved in Japan: Tofogliflozin".Pharmaceuticals and Medical Devices Agency (PMDA), Japan. Retrieved9 April 2025.
^Scheen AJ (October 2020). "Pharmacodynamics, efficacy and safety of SGLT2 inhibitors across the spectrum of type 2 diabetes mellitus".Diabetes & Metabolism.46 (5):373–387.doi:10.1016/j.diabet.2019.12.006.PMID 31924390.

Oraldiabetes medication,insulins andinsulin analogues, and other drugs used in diabetes (A10)

Insulins andinsulin analogues

Fast-acting	Insulin aspart Insulin glulisine Insulin lispro
Short-acting	Regular insulin^#
Long-acting	Insulin detemir^# Insulin glargine^# (+lixisenatide) NPH insulin Lente insulin^‡ Ultralente insulin^‡
Ultra-long-acting	Insulin degludec^# (+insulin aspart,+liraglutide) Insulin icodec^† (+semaglutide)
Inhalable	Exubera^‡ Afrezza
Oral	Insulin tregopil^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Non-insulins

Insulin sensitizers

Biguanides	Buformin^‡ Metformin^# Phenformin^‡
TZDs ("-glitazones") andPPAR agonists	Ciglitazone^§ Darglitazone^§ Englitazone^§ Lobeglitazone Netoglitazone^§ Pioglitazone Rivoglitazone^† Rosiglitazone Troglitazone^‡
Dual PPAR agonists	Aleglitazar^† Muraglitazar^§ Saroglitazar Tesaglitazar^§
Amylin analogues andDACRAs	Cagrilintide^§ Pramlintide

Secretagogues

K⁺_ATP

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

GLP-1 receptor agonists

GLP1 poly-agonist peptides	Mazdutide (GLP-1/GCGR) Retatrutide^§ (GLP-1/GIP/GCGR) Tirzepatide (GLP-1/GIP)

DPP-4 inhibitors ("-gliptins")

Other

Aldose reductase inhibitors	Epalrestat Fidarestat^§ Ranirestat^† Tolrestat^‡ Zenarestat^§
Alpha-glucosidase inhibitors	Acarbose Miglitol Voglibose
SGLT2 inhibitors ("-gliflozins")	Canagliflozin Dapagliflozin Empagliflozin^# Ertugliflozin Ipragliflozin Luseogliflozin Remogliflozin^§ Sergliflozin^§ Sotagliflozin Tofogliflozin^† Velagliflozin
Other	Benfluorex^‡ Bromocriptine Imeglimin

Combinations

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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

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