licogliflozin   Click here for help

GtoPdb Ligand ID: 10654

Synonyms: example 62 [WO2011048112A1] | LIK-066 | LIK066
Compound class: Synthetic organic
Comment: Licogliflozin (LIK-066) is an orally bioactive inhibitor of sodium/glucose cotransporters 1 and 2 (SGLT1, SGLT2). It was developed by Novartis for the treatment of obesity, non-alcoholic steatohepatitis, and type 2 diabetes, but the program was discontinued in 2018 [3].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 108.61
Molecular weight 416.18
XLogP 2.44
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC[C@H]1O[C@@H](c2ccc(c(c2)Cc2ccc3c(c2)OCCO3)CC)[C@@H]([C@H]([C@@H]1O)O)O
Isomeric SMILES OC[C@H]1O[C@@H](c2ccc(c(c2)Cc2ccc3c(c2)OCCO3)CC)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C23H28O7/c1-2-14-4-5-15(23-22(27)21(26)20(25)19(12-24)30-23)11-16(14)9-13-3-6-17-18(10-13)29-8-7-28-17/h3-6,10-11,19-27H,2,7-9,12H2,1H3/t19-,20-,21+,22-,23+/m1/s1
InChI Key XFJAMQQAAMJFGB-ZQGJOIPISA-N
No information available.
Summary of Clinical Use Click here for help
Licogliflozin (LIK-066) was progressed to clinical trials by Novartis for the treatment of obesity, non-alcoholic steatohepatitis, and type 2 diabetes. Unfortunately due to slow enrollment for Phase 2 trial NCT03152552, which would preclude the study being completed in a timely manner, Novartis decided to discontinue the study in 2018 [3].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01824264 Dose-finding Study of LIK066 Compared With Placebo or Sitagliptin to Evaluate Change in HbA1c in Patients With Diabetes Phase 2 Interventional Novartis
NCT03152552 A Dose Finding Study to Assess the Effect of LIK066 Compared to Placebo or Empagliflozin in Patients With Type 2 Diabetes Mellitus and Heart Failure Phase 2 Interventional Novartis Results from this study were published in 2020. Due to slow enrollment the study was prematurely terminated when only 142 patients had been recruited (125 were randomised). Becausete sample sizes were smaller thatn planned no firm conclusions could be made on the efficacy of licogliflozin in patients with T2DM and HF, although the 10 mg test dose did produce a significant effect. 2