meropenem   Click here for help

GtoPdb Ligand ID: 10829

Synonyms: ICI 194,660 | Merrem® | SM-7338
PDB Ligand
Compound class: Synthetic organic
Comment: Meropenem is a parenterally delivered, broad-spectrum carbapenem antibiotic. 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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
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 1218, 148
Other databases
BindingDB Ligand 50129062
CAS Registry No. 96036-03-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL127
DrugBank Ligand DB00760
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
Search UniChem for chemical match using the InChIKey DMJNNHOOLUXYBV-PQTSNVLCSA-N
Search UniChem for chemicals with the same backbone DMJNNHOOLUXYBV