linagliptin   Click here for help

GtoPdb Ligand ID: 6318

Synonyms: BI-1356 | Tradjenta®
Approved drug PDB Ligand
linagliptin is an approved drug (EMA & FDA (2011))
Compound class: Synthetic organic
Comment: Linagliptin is a once-daily, oral dipeptidyl peptidase-4 (DPP-4) inhibitor class anti-diabetic drug.
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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

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View more information in the IUPHAR Pharmacology Education Project: linagliptin

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 7
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 116.86
Molecular weight 472.23
XLogP 3.92
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 CC#CCn1c(nc2c1c(=O)n(Cc1nc(C)c3c(n1)cccc3)c(=O)n2C)N1CCCC(C1)N
Isomeric SMILES CC#CCn1c(nc2c1c(=O)n(Cc1nc(C)c3c(n1)cccc3)c(=O)n2C)N1CCC[C@H](C1)N
InChI InChI=1S/C25H28N8O2/c1-4-5-13-32-21-22(29-24(32)31-12-8-9-17(26)14-31)30(3)25(35)33(23(21)34)15-20-27-16(2)18-10-6-7-11-19(18)28-20/h6-7,10-11,17H,8-9,12-15,26H2,1-3H3/t17-/m1/s1
InChI Key LTXREWYXXSTFRX-QGZVFWFLSA-N
No information available.
Summary of Clinical Use Click here for help
Used in the management of type 2 diabetes.
Linagliptin was assessed in a combination therapy with the SGLT-2 inhibitor, empagliflozin with ClinicalTrials.gov ID NCT01734785. In February 2015, this translated to US FDA approval for the fixed dose formulation Glyxambi® (empagliflozin and linagliptin) for the treatment of type 2 diabetes.
In July 2016, the FDA approved a once-daily, extended release DPP-4 inhibitor/biguanide combination (Jentadueto XR®: linagliptin and metformin hydrochloride) as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Competitively and reversibly inhibits dipeptidyl peptidase, the enzyme which catalyses the breakdown of GLP-1. The resulting elevation of GLP-1 levels leads to increased production and release of insulin from pancreatic beta cells and decreased release of glucagon from pancreatic alpha cell. This leads to a decrease in glucose production in the liver and an increase of insulin.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)