Tofogliflozin

{{short description|Chemical compound}}

{{Drugbox

| drug_name = Tofogliflozin monohydrate

| 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)

| image = Tofogliflozin monohydrate skeletal 3D.svg

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| legal_status = Investigational

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| CAS_number = 1201913-82-7

| CAS_supplemental =
{{CAS|903565-83-3}} (anhydrous)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = P8DD8KX4O4

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| ATC_prefix = None

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| PubChem = 46908928

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| ChemSpiderID = 28527871

| ChEMBL = 2105711

| KEGG = D09978

| synonyms = CSG452

| C = 22 | H = 28 | O = 7

| smiles = CCc1ccc(cc1)Cc2ccc3c(c2)[C@]4([C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC3.O

| StdInChI = 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

| StdInChIKey = ZXOCGDDVNPDRIW-NHFZGCSJSA-N

}}

Tofogliflozin (INN,{{cite web|title=International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 65|url=https://www.who.int/entity/medicines/publications/druginformation/innlists/RL65.pdf|publisher=World Health Organization|access-date=15 November 2016}}{{rp|88}} USAN, codenamed CSG452) is a drug developed for the treatment of diabetes mellitus type 2 and was originally co-developed by Chugai Pharma in collaboration with Kowa and Sanofi.[http://www.chugai-pharm.co.jp/hc/ss/english/ir/reports_downloads/pipeline.html Chugai Pharmaceutical: Development Pipeline] 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 2014, tofogliflozin was approved for use in Japan and is marketed under the brand names Apleway and Deberza.{{cite journal |vauthors=Yabe D, Iwasaki M, Kuwata H, Kurose T, Harashima S, Hamasaki A, Seino Y |title=Efficacy and safety of tofogliflozin in Japanese patients with type 2 diabetes mellitus: A pooled analysis of phase 3 trials |journal=Journal of Diabetes Investigation |volume=12 |issue=3 |pages=431–441 |date=March 2021 |doi=10.1111/jdi.13379 |pmid=33176360|pmc=8015831 }}{{cite web |title=Drugs Approved in Japan: Tofogliflozin |url=https://www.pmda.go.jp/english/review-services/reviews/approved-information/drugs/0001.html |website=Pharmaceuticals and Medical Devices Agency (PMDA), Japan |access-date=9 April 2025}} It has not been approved for use outside of Japan.{{cite journal |vauthors=Scheen AJ |title=Pharmacodynamics, efficacy and safety of SGLT2 inhibitors across the spectrum of type 2 diabetes mellitus |journal=Diabetes & Metabolism |volume=46 |issue=5 |pages=373–387 |date=October 2020 |doi=10.1016/j.diabet.2019.12.006 |pmid=31924390}}