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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 of TOFOGLIFLOZIN ANHYDROUS

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

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.9 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
DEBERZA

Approved Use

The treatment of type 2 diabetes mellitus.

Launch Date

2012
PubMed

PubMed

TitleDatePubMed
Patents

Patents

20070275907
2
20090030006
2

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
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 GMT 2023 , Edited by admin on Fri Dec 15 19:47:54 GMT 2023
Code System Code Type Description
FDA UNII
554245W62T
Created by admin on Fri Dec 15 19:47:53 GMT 2023 , Edited by admin on Fri Dec 15 19:47:53 GMT 2023
PRIMARY
CAS
903565-83-3
Created by admin on Fri Dec 15 19:47:53 GMT 2023 , Edited by admin on Fri Dec 15 19:47:53 GMT 2023
PRIMARY
NCI_THESAURUS
C152676
Created by admin on Fri Dec 15 19:47:53 GMT 2023 , Edited by admin on Fri Dec 15 19:47:53 GMT 2023
PRIMARY
EVMPD
SUB177215
Created by admin on Fri Dec 15 19:47:53 GMT 2023 , Edited by admin on Fri Dec 15 19:47:53 GMT 2023
PRIMARY
PUBCHEM
46908929
Created by admin on Fri Dec 15 19:47:54 GMT 2023 , Edited by admin on Fri Dec 15 19:47:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID90238097
Created by admin on Fri Dec 15 19:47:53 GMT 2023 , Edited by admin on Fri Dec 15 19:47:53 GMT 2023
PRIMARY
MERCK INDEX
m11867
Created by admin on Fri Dec 15 19:47:53 GMT 2023 , Edited by admin on Fri Dec 15 19:47:53 GMT 2023
PRIMARY
SMS_ID
100000163089
Created by admin on Fri Dec 15 19:47:54 GMT 2023 , Edited by admin on Fri Dec 15 19:47:54 GMT 2023
PRIMARY
INN
9275
Created by admin on Fri Dec 15 19:47:53 GMT 2023 , Edited by admin on Fri Dec 15 19:47:53 GMT 2023
PRIMARY
Related Record Type Details
Structure of TOFOGLIFLOZIN
SALT/SOLVATE -> PARENT
Structure of TOFOGLIFLOZIN
SOLVATE->ANHYDROUS
SODIUM/GLUCOSE COTRANSPORTER 2
TARGET -> INHIBITOR
Related Record Type Details
Structure of 2-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ACETIC ACID
METABOLITE INACTIVE -> PARENT
20.4 EXCRETED IN FECES
MAJOR
FECAL
Structure of 2-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ACETIC ACID
METABOLITE INACTIVE -> PARENT
76% OF TOTAL DOSE EXCRETED IN URINE;
MAJOR
URINE
Structure of 1-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ETHANONE
METABOLITE -> PARENT
MINOR
FECAL; PLASMA; URINE
Structure of 1-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ETHANONE
METABOLITE -> PARENT
PERCENT OF TOTAL DOSE
URINE
Structure of 2-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ACETIC ACID
METABOLITE INACTIVE -> PARENT
MAJOR
FECAL; PLASMA; URINE
Structure of 1-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ETHANONE
METABOLITE -> PARENT
PERCENT OF AUC
PLASMA
Structure of 2-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ACETIC ACID
METABOLITE INACTIVE -> PARENT
TAKEN FROM AUC
MAJOR
PLASMA
Structure of 1-(4-(((3S,3'R,4'S,5'S,6'R)-3',4',5'-TRIHYDROXY-6'-(HYDROXYMETHYL)SPIRO(1H-ISOBENZOFURAN-3,2'-TETRAHYDROPYRAN)-5-YL)METHYL)PHENYL)ETHANONE
METABOLITE -> PARENT
PERCENT OF TOTAL DOSE
FECAL
Related Record Type Details
Structure of TOFOGLIFLOZIN ANHYDROUS
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