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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Targets

Primary TargetPharmacologyConditionPotency
0.877 nM [IC50]
1960.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ERTUGLIFLOZIN
Primary
STEGLATRO

Cmax

ValueDoseCo-administeredAnalytePopulation
81.3 ng/mL
5 mg 1 times / day steady-state, oral
ERTUGLIFLOZIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
398 ng × h/mL
5 mg 1 times / day steady-state, oral
ERTUGLIFLOZIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
16.6 h
5 mg 1 times / day steady-state, oral
ERTUGLIFLOZIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
6.4%
5 mg 1 times / day steady-state, oral
ERTUGLIFLOZIN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

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
Record UNII
6C282481IP
Record Status Validated (UNII)
Record Version