insulin glargine   Click here for help

GtoPdb Ligand ID: 7572

Synonyms: HOE-901 | HOE901 | Lantus®
Approved drug
insulin glargine is an approved drug (FDA and EMA (2000))
Compound class: Peptide
Comment: Insulin glargine is a recombinant, modified analogue of human insulin. The chemical structure shown here was generated using the SMILES from PubChem CID 44146714.

A number of insulin glargine biosimilars have been approved internationally since the expiration of patents on Lantus® in 2014: a comprehensive list that is maintained by the Generics and Biosimilar Initiative (https://www.gabionline.net) is available here. The first fully interchangeable biosimilar to be FDA approved was Semglee® (insulin glargine-yfgn; Mylan Pharmaceuticals), in July 2021.
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View more information in the IUPHAR Pharmacology Education Project: glargine

insulin glargine 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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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 NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCNC(=N)N)CCCNC(=N)N)[C@H](O)C)NC(=O)[C@@H]1CCCN1C(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC(=O)[C@@H]1CSSC[C@H](NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@@H]2CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@H](CC)C)NC(=O)CN)CCC(=O)O)CCC(=O)N)C(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CC(C)C)Cc1ccc(cc1)O)CC(C)C)C)CCC(=O)O)C(C)C)CC(C)C)Cc1[nH]cnc1)CO)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc1ccccc1)N)CC(=O)N)CCC(=O)N)Cc1[nH]cnc1)CC(C)C)C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)[C@H](CC)C)CO)[C@H](O)C)C(=O)NCC(=O)O)CCC(=O)O)CCCNC(=N)N)Cc1ccccc1)Cc1ccc(cc1)O
Isomeric SMILES CC[C@H](C)[C@H]1C(=O)N[C@H]2CSSC[C@@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC2=O)CO)CC(C)C)Cc2ccc(cc2)O)CCC(=O)N)CC(C)C)CCC(=O)O)CC(=O)N)Cc2ccc(cc2)O)C(=O)NCC(=O)O)C(=O)NCC(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)NCC(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccc(cc2)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)C(C)C)CC(C)C)Cc2ccc(cc2)O)CC(C)C)C)CCC(=O)O)C(C)C)CC(C)C)Cc2cnc[nH]2)CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](Cc2cnc[nH]2)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@H](Cc2ccccc2)N)C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CO)[C@@H](C)O)NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)CN
InChI Key COCFEDIXXNGUNL-RFKWWTKHSA-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
Used to treat diabetes types 1 and 2.

A fixed-ratio formulation containing insulin glargine and lixisenatide is being assessed in clinical trials for the treatment of type 2 diabetes. Click here to view a list of such trials registered with ClinicalTrials.gov
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The amino acid modifications in insulin glargine do not alter the pharmocological effect of the insulin, but alter the drug's pharmacokinetics/pharmacodynamics. Insulin glargine crystalises at physiological pH when injected subcutaneously. These crystals dissolve slowly and provide a more regular and longer-lasting release of insulin into the bloodstream compared to natural insulin.
External links Click here for help
For extended ADME data see the following:

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