TOFOGLIFLOZIN

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26O6.H2O
Molecular Weight	404.4535
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CCC1=CC=C(CC2=CC=C3CO[C@]4(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C3=C2)C=C1

InChI

InChIKey=ZXOCGDDVNPDRIW-NHFZGCSJSA-N

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

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C22H26O6
Molecular Weight	386.4382
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848755 | http://www.kowa-souyaku.co.jp/upload/item/66/93/7-wse_167.doc

Tofogliflozin is a SGLT2 selective inhibitor which was developed by Chugai Pharmaceutical for the treatment of Type 2 Diabetes Mellitus. The drug was approved in Japan in 2013 and it is being marketed under the names Apleway and Debereza.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 2 25 Target ID: CHEMBL3884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22889351	Inhibitor 8297		2.9 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848755	Primary		Approved 8429	DEBERZA Approved Use The treatment of type 2 diabetes mellitus. Launch Date 2012

PubMed

Title	Date	PubMed
Tofogliflozin, a potent and highly specific sodium/glucose cotransporter 2 inhibitor, improves glycemic control in diabetic rats and mice.	2012 Jun	22410641
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.	2012 Sep 13	22889351
In vitro-in vivo correlation of the inhibition potency of sodium-glucose cotransporter inhibitors in rat: a pharmacokinetic and pharmacodynamic modeling approach.	2013 Apr	23386251
Selective SGLT2 inhibition by tofogliflozin reduces renal glucose reabsorption under hyperglycemic but not under hypo- or euglycemic conditions in rats.	2013 Feb 15	23249697

Patents

Sample Use Guides

In Vivo Use Guide

In general, for adults, take 20 mg of tofogliflozin once a day, before or after breakfast.

Route of Administration: Oral

In Vitro Use Guide

Primary cultured proximal tubular epithelial cells from human normal kidney were treated with or without 3 nM or 30 nM tofogliflozin and with or without 22.8 mM glucose. Tofogliflozin dose-dependently suppressed glucose entry into tubular cells.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:47:53 GMT 2023` Edited by `admin` on `Fri Dec 15 19:47:53 GMT 2023`
Record UNII	P8DD8KX4O4
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TOFOGLIFLOZIN

Official Name

English

SPIRO(ISOBENZOFURAN-1(3H),2'-(2H)PYRAN)-3',4',5'-TRIOL,6-((4-ETHYLPHENYL)METHYL)-3',4',5',6'-TETRAHYDRO-6'-(HYDROXYMETHYL)-,HYDRATE (1:1),(1S,3'R,4'S,5'S,6'R)-

Common Name

English

TOFOGLIFLOZIN MONOHYDRATE

Common Name

English

TOFOGLIFLOZIN MONOHYDRATE [MI]

Common Name

English

TOFOGLIFLOZIN HYDRATE

Common Name

English

CSG452

Code

English

TOFOGLIFLOZIN [USAN]

Common Name

English

TOFOGLIFLOZIN HYDRATE [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98083