sotagliflozin   Click here for help

GtoPdb Ligand ID: 8312

Synonyms: Inpefa® | LX-4211 | LX4211 | Zynquista®
Approved drug PDB Ligand
sotagliflozin is an approved drug (EMA (2019), FDA (2023))
Compound class: Synthetic organic
Comment: Sotagliflozin is a dual inhibitor of the sodium/glucose cotransporters 1 and 2 (SGLT1/2) [5,8]. SGLT1 and SGLT2 mediate glucose reabsorption, by the kidney and in the gastrointestinal tract respectively.
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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

sotagliflozin is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 4
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 104.45
Molecular weight 424.11
XLogP 3.9
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)C1OC(SC)C(C(C1O)O)O
Isomeric SMILES CCOc1ccc(cc1)Cc1cc(ccc1Cl)[C@@H]1O[C@H](SC)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1
InChI Key QKDRXGFQVGOQKS-CRSSMBPESA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Sotagliflozin received EMA marketing authorisation in April 2019, as a treatment for type I diabetes mellitus in overweight patients for whom insulin alone fails to adequately control blood sugar. It is to be used in combination with insulin therapy to improve glycemic control in these patients. Sotagliflozin was also investigated as an option to treat heart failure [1-2,6-7]. Based on evidence of efficacy in clinical studies, the FDA approved sotagliflozin (in May 2023) to reduce deaths and hospitalisations of patients with heart failure (or at risk of heart failure) with both preserved and reduced left ventricular ejection fraction.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Sotagliflozin combines inhibition of both renal SGLT2 activity with inhibition of intestinal SGLT1 activity. This combined action represents a novel approach to the treatment of diabetes, as current approved drugs of this type (such as dapagliflozin, empagliflozin and canagliflozin) have focussed on selectively inhibiting SGLT2. The dual action appears to provide effective glycemic control with reduced gastrointestinal side effects compared to current SGLT2 inhibitors [8].
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03521934 Effect of Sotagliflozin on Cardiovascular Events in Participants With Type 2 Diabetes Post Worsening Heart Failure (SOLOIST-WHF Trial) Phase 3 Interventional Lexicon Pharmaceuticals The SOLOIST-WHF trial 4,7
NCT03315143 Effect of Sotagliflozin on Cardiovascular and Renal Events in Participants With Type 2 Diabetes and Moderate Renal Impairment Who Are at Cardiovascular Risk Phase 3 Interventional Lexicon Pharmaceuticals The SCORED trial 3
External links Click here for help
For extended ADME data see the following:

European Medicines Agency (EMA)