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
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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)
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Clinical data |
Legal status |
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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
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CCc1ccc(cc1)Cc2ccc3c(c2)[C@]4([C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC3.O
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InChI
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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
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Key:ZXOCGDDVNPDRIW-NHFZGCSJSA-N
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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.[1] 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[update], the drug is in Phase III clinical trials.[2][3]
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.[4]
References
- ^ 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)
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Insulin |
Sensitizers |
Biguanides |
- Metformin#
- Buformin<sp>‡
- Phenformin‡
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TZDs/"glitazones" (PPAR) |
- Ciglitazone§
- Darglitazone§
- Englitazone§
- Lobeglitazone
- Netoglitazone§
- Pioglitazone
- Rivoglitazone†
- Rosiglitazone
- Troglitazone‡
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Dual PPAR agonists |
- Aleglitazar†
- Muraglitazar§
- Saroglitazar
- Tesaglitazar§
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Secretagogues |
K+ ATP |
Sulfonylureas |
- 1st generation: Acetohexamide
- Carbutamide
- Chlorpropamide
- Metahexamide
- Tolbutamide
- Tolazamide
- 2nd generation: Glibenclamide (Glyburide)#
- Glibornuride
- Glicetanile
- Gliclazide
- Gliflumide
- Glipizide
- Gliquidone
- Glisoxepide
- Glyclopyramide
- Glimepiride
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Meglitinides/"glinides" |
- Nateglinide
- Repaglinide
- Mitiglinide
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GLP-1 agonists |
- Exenatide
- Liraglutide
- Taspoglutide†
- Albiglutide†
- Lixisenatide
- Dulaglutide
- Semaglutide
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DPP-4 inhibitors |
- Alogliptin
- Anagliptin
- Gemigliptin
- Linagliptin
- Omarigliptin
- Saxagliptin
- Sitagliptin
- Teneligliptin
- Vildagliptin
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GPR40 Free fatty acid receptor 1 |
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Analogs/other insulins |
- fast-acting (Insulin lispro
- Insulin aspart
- Insulin glulisine)
- short-acting (Regular insulin)
- long-acting (Insulin glargine
- Insulin detemir
- NPH insulin)
- ultra-long-acting (Insulin degludec†)
- inhalable Exubera‡
- Afrezza
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Other |
Aldose reductase inhibitors |
- Epalrestat
- Fidarestat§
- Ranirestat†
- Tolrestat‡
- Zenarestat§
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Alpha-glucosidase inhibitors |
- Acarbose
- Miglitol
- Voglibose
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Amylin analog |
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Sodium glucose transporter (SGLT2) inhibitors |
- Canagliflozin
- Dapagliflozin
- Empagliflozin
- Remogliflozin§
- Sergliflozin§
- Tofogliflozin†
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Other |
- Benfluorex‡
- Bromocriptine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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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
Related Links
- 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 ...
- 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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