Compound ID | 1868

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Benapenem

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: 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, similar to ertapenem; clinical development only for China
Institute where first reported: Sihuan Pharmaceutical
Year first mentioned: 2015
Highest development stage: Phase 2/ Phase 3 (NCT04505683)
Development status: Active
Chemical structure(s):
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Molecular weight: 524.61
Iso. SMILES: C[C@@H]1[C@@H]2[C@H](C(=O)N2C(=C1S[C@H]3C[C@H](NC3)C(=O)NCC4=CC=C(C=C4)S(=O)(=O)N)C(=O)O)[C@@H](C)O
InChI Key: JNSMRGMLNPEWLR-PDCLSYJBSA-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)NCC4=CC=C(C=C4)S(=O)(=O)N)NC3)C(=O)O
InChI: InChI=1S/C22H28N4O7S2/c1-10-17-16(11(2)27)21(29)26(17)18(22(30)31)19(10)34-13-7-15(24-9-13)20(28)25-8-12-3-5-14(6-4-12)35(23,32)33/h3-6,10-11,13,15-17,24,27H,7-9H2,1-2H3,(H,25,28)(H,30,31)(H2,23,32,33)/t10-,11-,13+,15+,16-,17-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/58326208
Guide to Pharmacology: benapenem
Citation: https://journals.asm.org/doi/10.1128/AAC.02188-18

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