gepotidacin   Click here for help

GtoPdb Ligand ID: 10817

Synonyms: Blujepa® | GSK-2140944 | GSK2140944
Approved drug PDB Ligand
gepotidacin is an approved drug
Compound class: Synthetic organic
Comment: Gepotidacin (formerly GSK2140944) is a novel, first-in-class, triazaacenaphthylene antibacterial that inhibits bacterial DNA gyrase and topoisomerase IV via a unique mechanism [2-3]. It was developed for potential to treat conventional and biothreat pathogens including MRSA, respiratory tract infections, acute bacterial skin and skin structure infections (ABSSI) [6,8], and uncomplicated urogenital gonorrhea [5].

gepotidacin 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 1
Rotatable bonds 5
Topological polar surface area 94.28
Molecular weight 448.22
XLogP 1.63
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 O=c1cnc2c3n1[C@H](CN1CCC(CC1)NCc1ncc4c(c1)CCCO4)Cn3c(=O)cc2
Isomeric SMILES O=c1cnc2c3n1[C@H](CN1CCC(CC1)NCc1ncc4c(c1)CCCO4)Cn3c(=O)cc2
InChI InChI=1S/C24H28N6O3/c31-22-4-3-20-24-29(22)15-19(30(24)23(32)13-27-20)14-28-7-5-17(6-8-28)25-11-18-10-16-2-1-9-33-21(16)12-26-18/h3-4,10,12-13,17,19,25H,1-2,5-9,11,14-15H2/t19-/m1/s1
InChI Key PZFAZQUREQIODZ-LJQANCHMSA-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (2025)
IUPAC Name Click here for help
(3R)-3-[[4-(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethylamino)piperidin-1-yl]methyl]-1,4,7-triazatricyclo[6.3.1.04,12]dodeca-6,8(12),9-triene-5,11-dione
International Nonproprietary Names Click here for help
INN number INN
10050 gepotidacin
Synonyms Click here for help
Blujepa® | GSK-2140944 | GSK2140944
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Gepotidacin
Other databases
BindingDB Ligand 50050549
CAS Registry No. 1075236-89-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL3317856
DrugBank Ligand DB12134
GtoPdb PubChem SID 405560258
PubChem CID 25101874
RCSB PDB Ligand JHN
Search Google for chemical match using the InChIKey PZFAZQUREQIODZ-LJQANCHMSA-N
Search Google for chemicals with the same backbone PZFAZQUREQIODZ
Search PubMed clinical trials gepotidacin
Search PubMed titles gepotidacin
Search PubMed titles/abstracts gepotidacin
UniChem Compound Search for chemical match using the InChIKey PZFAZQUREQIODZ-LJQANCHMSA-N
UniChem Connectivity Search for chemical match using the InChIKey PZFAZQUREQIODZ-LJQANCHMSA-N

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MedChemExpress
Gepotidacin (links to external site)
Cat. No. HY-16742