ertugliflozin   Click here for help

GtoPdb Ligand ID: 8376

Synonyms: MK-8835 | PF-04971729 | Steglatro®
Approved drug
ertugliflozin is an approved drug (FDA (2017), EMA (2018))
Compound class: Synthetic organic
Comment: Ertugliflozin (PF-04971729) is an inhibitor of sodium/glucose cotransporter 2 (SGLT2). The discovery of PF-04971729 is reported in [2], where it is compound 4.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 108.61
Molecular weight 436.13
XLogP 2.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)C12OCC(O1)(CO)C(C(C2O)O)O
Isomeric SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)[C@]12OC[C@@](O1)(CO)[C@H]([C@@H]([C@H]2O)O)O
InChI 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
InChI Key MCIACXAZCBVDEE-CUUWFGFTSA-N
Bioactivity Comments
Ertugliflozin is >2200 fold selective for SGLT2 compared to SGLT1 [2].
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Sodium/glucose cotransporter 2 Primary target of this compound Hs Inhibitor Inhibition 9.1 pIC50 - 2
pIC50 9.1 (IC50 8.77x10-10 M) [2]
Sodium/glucose cotransporter 1 Hs Inhibitor Inhibition 5.7 pIC50 - 2
pIC50 5.7 (IC50 1.96x10-6 M) [2]