meropenem   Click here for help

GtoPdb Ligand ID: 10829

Synonyms: ICI 194,660 | Merrem® | SM-7338
Approved drug PDB Ligand
meropenem is an approved drug (FDA (1996), EMA (2018))
Compound class: Synthetic organic
Comment: Meropenem is a parenterally delivered, broad-spectrum carbapenem antibacterial. It is active against Gram-positive and Gram-negative bacteria, and is effective against aerobic and anaerobic pathogens including Klebsiella, E. coli, Enterococcus, Clostridium spp.
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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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Click here for structure editor
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 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 135.48
Molecular weight 383.15
XLogP -0.78
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 C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)O)S[C@@H]1CN[C@@H](C1)C(=O)N(C)C)O
Isomeric SMILES C[C@H]([C@H]1C(=O)N2[C@@H]1[C@@H](C)C(=C2C(=O)O)S[C@@H]1CN[C@@H](C1)C(=O)N(C)C)O
InChI InChI=1S/C17H25N3O5S/c1-7-12-11(8(2)21)16(23)20(12)13(17(24)25)14(7)26-9-5-10(18-6-9)15(22)19(3)4/h7-12,18,21H,5-6H2,1-4H3,(H,24,25)/t7-,8-,9+,10+,11-,12-/m1/s1
InChI Key DMJNNHOOLUXYBV-PQTSNVLCSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1996), EMA (2018))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(4R,5S,6S)-3-[(3S,5S)-5-(dimethylcarbamoyl)pyrrolidin-3-yl]sulfanyl-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
International Nonproprietary Names Click here for help
INN number INN
6396 meropenem
Synonyms Click here for help
ICI 194,660 | Merrem® | SM-7338
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Meropenem, ICI 194,660
Reactome Drug Reactome logo R-ALL-9695385
Reactome Reaction Reactome logo R-HSA-9695415
Other databases
BindingDB Ligand 50129062
CAS Registry No. 96036-03-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL127
DrugBank Ligand DB00760
DrugCentral Ligand 1709
GtoPdb PubChem SID 405560270
PubChem CID 441130
RCSB PDB Ligand MEM
Search Google for chemical match using the InChIKey DMJNNHOOLUXYBV-PQTSNVLCSA-N
Search Google for chemicals with the same backbone DMJNNHOOLUXYBV
Search PubMed clinical trials meropenem
Search PubMed titles meropenem
Search PubMed titles/abstracts meropenem
UniChem Compound Search for chemical match using the InChIKey DMJNNHOOLUXYBV-PQTSNVLCSA-N
UniChem Connectivity Search for chemical match using the InChIKey DMJNNHOOLUXYBV-PQTSNVLCSA-N