TOFOGLIFLOZIN ANHYDROUS

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26O6
Molecular Weight	386.4382
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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=VWVKUNOPTJGDOB-BDHVOXNPSA-N

InChI=1S/C22H26O6/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/t18-,19-,20+,21-,22+/m1/s1

HIDE SMILES / InChI

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 1.35699838E12

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 UTC 2023` Edited by `admin` on `Fri Dec 15 19:47:53 UTC 2023`
Record UNII	554245W62T
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TOFOGLIFLOZIN ANHYDROUS

Common Name

English

CSG452

Code

English

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

Systematic Name

English

CSG-452

Code

English

RO-4998452

Code

English

RO4998452

Code

English

TOFOGLIFLOZIN [MI]

Common Name

English

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

Common Name

English

tofogliflozin [INN]

Common Name

English

R-7201

Code

English

Tofogliflozin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C98083

Created by admin on Fri Dec 15 19:47:54 UTC 2023 , Edited by admin on Fri Dec 15 19:47:54 UTC 2023

Code System Code Type Description

FDA UNII

554245W62T

Created by admin on Fri Dec 15 19:47:53 UTC 2023 , Edited by admin on Fri Dec 15 19:47:53 UTC 2023

PRIMARY

CAS

903565-83-3

Created by admin on Fri Dec 15 19:47:53 UTC 2023 , Edited by admin on Fri Dec 15 19:47:53 UTC 2023

PRIMARY

NCI_THESAURUS

C152676

Created by admin on Fri Dec 15 19:47:53 UTC 2023 , Edited by admin on Fri Dec 15 19:47:53 UTC 2023

PRIMARY

EVMPD

SUB177215

Created by admin on Fri Dec 15 19:47:53 UTC 2023 , Edited by admin on Fri Dec 15 19:47:53 UTC 2023

PRIMARY

PUBCHEM

46908929

Created by admin on Fri Dec 15 19:47:54 UTC 2023 , Edited by admin on Fri Dec 15 19:47:54 UTC 2023

PRIMARY

EPA CompTox

DTXSID90238097

Created by admin on Fri Dec 15 19:47:53 UTC 2023 , Edited by admin on Fri Dec 15 19:47:53 UTC 2023

PRIMARY

MERCK INDEX

m11867

Created by admin on Fri Dec 15 19:47:53 UTC 2023 , Edited by admin on Fri Dec 15 19:47:53 UTC 2023

PRIMARY

SMS_ID

100000163089

Created by admin on Fri Dec 15 19:47:54 UTC 2023 , Edited by admin on Fri Dec 15 19:47:54 UTC 2023

PRIMARY

INN

9275

Created by admin on Fri Dec 15 19:47:53 UTC 2023 , Edited by admin on Fri Dec 15 19:47:53 UTC 2023

PRIMARY

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Amount:


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Comments:

PERCENT OF AUC

Qualification:

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Amount:


					7XFR17ALIV

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ACTIVE MOIETY

Amount:

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

PubMed

Patents

Sample Use Guides

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