Compound ID | 1862

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Meropenem

Synonym(s): ICI 194,660  |  SM-7338  |  SM7338  |  SM 7338

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds to bacterial penicillin-binding proteins (PBP) and interferes with bacterial cell wall integrity and synthesis; carbapenems bind to all PBPs, with PBP2 and PBP4 as the highest-affinity targets; carbapenems have a very broad spectrum including non-fermenters and are not hydrolysed by most beta-lactamases with exception of carbapenemases; PBP inhibitor
Description: Semisynthetic, derived from thienamycin. Fixed combinations with various beta-lactamase inhibitors
Institute where first reported: Pfizer
Year first mentioned: 1983
Highest development stage: Approved by FDA in 1996
Development status: Approved
Chemical structure(s):
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Molecular weight: 383.46
Iso. SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)N(C)C)C(=O)O)[C@@H](C)O
InChI Key: DMJNNHOOLUXYBV-PQTSNVLCSA-N
Can. SMILES: C[C@@H]1[C@@H]2[C@@H]([C@@H](C)O)C(=O)N2C(=C1S[C@H]3C[C@@H](C(=O)N(C)C)NC3)C(=O)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
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/441130
Guide to Pharmacology: meropenem
Citations:
  • https://journals.asm.org/doi/full/10.1128/AAC.00282-18
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6143100/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9031024/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC245547/

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