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.
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2D Structure
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Physico-chemical Properties
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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
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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
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Summary of Clinical Use Click here for help
The FDA granted approval for meropenem as a monotherapy in 1996; indicated for complicated infections of the skin or stomach and bacterial meningitis. In the EU, meropenem is approved for use in fixed-dose combination with vaborbactam (Vaborem®, previosly called Vabomere). Vaborem was authorised by the EMA in 2018, and was indicated for complicated urinary tract (and kidney) infections, complicated intra-abdominal infections, and hospital-acquired and ventilator-associated pneumonias.
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