tofogliflozin

トホグリフロジン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/03/30 22:41:47」(JST)

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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 903565-83-3 (anhydrous)
ATC code	None
PubChem	CID 46908928
ChemSpider	28527871
KEGG	D09978
ChEMBL	CHEMBL2105711
Synonyms	CSG452
Chemical data
Formula	C22H28O7
Molar 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.

References

English Journal

• Tofogliflozin Improves Insulin Resistance in Skeletal Muscle and Accelerates Lipolysis in Adipose Tissue in Male Mice.

• Obata A1, Kubota N1,2,3,4, Kubota T1,3,4,5, Iwamoto M1, Sato H1, Sakurai Y1, Takamoto I1, Katsuyama H1, Suzuki Y6, Fukazawa M6, Ikeda S6, Iwayama K7, Tokuyama K7, Ueki K1, Kadowaki T1,2.
• Endocrinology.Endocrinology.2015 Dec 29:en20151588. [Epub ahead of print]
• SGLT2 inhibitors have attracted attention as they exert anti-diabetic and anti-obesity effects. In this study, we investigated the effects of tofogliflozin on glucose homeostasis and its metabolic consequences and clarified the underlying molecular mechanisms. C57BL/6 mice were fed normal chow (NC)
• PMID 26713783

• Body Weight Gain and Hyperphagia After Administration of SGLT-2 Inhibitor: A Case Report.

• Hamamoto H1, Noda M2.
• The American journal of case reports.Am J Case Rep.2015 Dec 7;16:863-7.
• BACKGROUND A detailed description is given of a case we encountered in which unexpectedly marked weight gain occurred following a treatment switch from a GLP-1 receptor agonist to an SGLT-2 inhibitor CASE REPORT The patient, a 44-year-old man with type 2 diabetes mellitus, had gained about 10 kg in
• PMID 26638727

• Sodium-glucose cotransporter-2 inhibitors and blood pressure decrease: a valuable effect of a novel antidiabetic class?

• Imprialos KP1, Sarafidis PA, Karagiannis AI.
• Journal of hypertension.J Hypertens.2015 Nov;33(11):2185-97. doi: 10.1097/HJH.0000000000000719.
• Diabetes mellitus is a major issue of public health, affecting more than 300 million people worldwide. Inhibitors of the sodium-glucose cotransporter-2 (SGLT-2) in the renal proximal tubule are a novel class of agents for the treatment of type 2 diabetes mellitus. Inhibition of the SGLT-2 results in
• PMID 26372321

Japanese Journal

• 日本で開発されたSGLT2阻害薬トホグリフロジンの可能性

• 内分泌・糖尿病・代謝内科 38(3), 297-302, 2014-03
• NAID 40020035044

Related Links

• Tofogliflozinとは - goo Wikipedia (ウィキペディア)

Tofogliflozinとは？goo Wikipedia (ウィキペディア) 。出典：Wikipedia（ウィキペディア）フリー百科事典。 Tofogliflozinとは - goo Wikipedia (ウィキペディア) gooトップ サイトマップ スタートページに設定 RSS ヘルプ メニューへスキップ メール ...

• Tofogliflozin, a novel sodium-glucose co-transporter 2 inhibitor ...

1. Br J Pharmacol. 2013 Oct;170(3):519-31. doi: 10.1111/bph.12269. Tofogliflozin, a novel sodium-glucose co-transporter 2 inhibitor, improves renal and pancreatic function in db/db mice. Nagata T(1), Fukuzawa T, Takeda M ...

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