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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H25ClO7
Molecular Weight 436.883
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERTUGLIFLOZIN

SMILES

CCOC1=CC=C(CC2=C(Cl)C=CC(=C2)[C@]34OC[C@](CO)(O3)[C@@H](O)[C@H](O)[C@H]4O)C=C1

InChI

InChIKey=MCIACXAZCBVDEE-CUUWFGFTSA-N
InChI=1S/C22H25ClO7/c1-2-28-16-6-3-13(4-7-16)9-14-10-15(5-8-17(14)23)22-20(27)18(25)19(26)21(11-24,30-22)12-29-22/h3-8,10,18-20,24-27H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H25ClO7
Molecular Weight 436.883
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ertugliflozin (PF-04971729) is a potent and selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor incorporating a unique dioxa-bicyclo[3.2.1]octane (bridged ketal) ring system. SGLT2 has become an important therapeutic target and several SGLT2-selective inhibitors are either approved or in clinical development for the management of blood glucose in patients with type 2 diabetes. Ertugliflozin demonstrated robust urinary glucose excretion in rats and an excellent preclinical safety profile. It was announced that FDA and EMA filing acceptances of three marketing applications for ertugliflozin-containing medicines for adults with type 2 diabetes.

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
STEGLATRO
Primary
ERTUGLIFLOZIN
PubMed

PubMed

TitleDatePubMed
From victim to ally: the kidney as an emerging target for the treatment of diabetes mellitus.
2009 Mar
Sodium glucose cotransporter 2 inhibitors as a new treatment for diabetes mellitus.
2010 Jan
Phase III, efficacy and safety study of ertugliflozin monotherapy in people with type 2 diabetes mellitus inadequately controlled with diet and exercise alone.
2017 May
Patents

Sample Use Guides

In Vivo Use Guide
Once-daily ertugliflozin (1, 5, 10 or 25 mg) for the 12-week treatment period.
Route of Administration: Oral
In Vitro Use Guide
Ertugliflozin (PF-04971729), at a concentration range of 1.4 to 1000 μM, was evaluated as an inhibitor of the hOCT2 transporter. The calculated IC50 for inhibition of hOCT2-mediated uptake of [14C]metformin by PF-04971729 was 917 uM. Under these experimental conditions, the positive control quinidine (1 mM) inhibited >80% [14C]metformin uptake mediated by hOCT2.
Substance Class Chemical
Created
by admin
on Mon Oct 21 23:22:59 UTC 2019
Edited
by admin
on Mon Oct 21 23:22:59 UTC 2019
Record UNII
6C282481IP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ERTUGLIFLOZIN
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
ERTUGLIFLOZIN [WHO-DD]
Common Name English
PF04971729
Code English
(1S,2S,3S,4R,5S)-5-(4-CHLORO-3-((4-ETHOXYPHENYL)METHYL)PHENYL)- 1-(HYDROXYMETHYL)-6,8-DIOXABICYCLO(3.2.1)OCTANE-2,3,4-TRIOL
Systematic Name English
ERTUGLIFLOZIN COMPONENT OF STELUJAN
Brand Name English
STEGLATRO
Brand Name English
.BETA.-L-IDOPYRANOSE, 1,6-ANHYDRO-1-C-(4-CHLORO-3-((4-ETHOXYPHENYL)METHYL)PHENYL)-5-C-(HYDROXYMETHYL)-
Common Name English
PF-04971729
Common Name English
ERTUGLIFLOZIN COMPONENT OF SEGLUROMET
Brand Name English
ERTUGLIFLOZIN [INN]
Common Name English
STELUJAN COMPONENT ERTUGLIFLOZIN
Brand Name English
SEGLUROMET COMPONENT ERTUGLIFLOZIN
Brand Name English
ERTUGLIFLOZIN [USAN]
Common Name English
PF-04971729-00
Code English
Classification Tree Code System Code
WHO-ATC A10BD24
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
WHO-ATC A10BK04
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
Code System Code Type Description
EPA CompTox
1210344-57-2
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
PRIMARY
CAS
1210344-57-2
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
PRIMARY
PUBCHEM
44814423
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
PRIMARY
ChEMBL
CHEMBL1770248
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
PRIMARY
EVMPD
SUB182716
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
PRIMARY
INN
9460
Created by admin on Mon Oct 21 23:22:59 UTC 2019 , Edited by admin on Mon Oct 21 23:22:59 UTC 2019
PRIMARY
Related Record Type Details
EXCRETED UNCHANGED
URINE
TARGET -> INHIBITOR
CHO CELLS STABLY EXPRESSING HUMAN SGLT2, MEASURING THE SODIUM DEPENDENT UPTAKE OF 14C-LABELED METHYL-ALPHA-D-GLUCOPYRANOSIDE (AMG) (N=10)
INHIBITOR
IC50
BINDER->LIGAND
BINDING
TRANSPORTER -> SUBSTRATE
CUMULATIVE EXCRETION
FECAL
TRANSPORTER -> INHIBITOR
IC50
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> INHIBITOR
IC50
TRANSPORTER -> SUBSTRATE
CUMULATIVE EXCRETION
URINE
METABOLIC ENZYME -> INHIBITOR
IC50
EXCRETED UNCHANGED
FECAL
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC DOSE
PHARMACOKINETIC
ROUTE OF ADMINISTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Tmax PHARMACOKINETIC ROUTE OF ADMINISTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC ROUTE OF ADMINISTRATION