Compound ID | 2879

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Nacubactam/Aztreonam (OP0595/Aztreonam)

Class: Beta-lactam + beta-lactamase inhibitor

Spectrum of activity: Gram-negative
Details of activity: Active against Enterobacteriaceae; nacubactam (OP0595) inhibits serine beta-lactamases and penicillin-binding protein 2 in Enterobacteriaceae additionally enhances beta-lactam agents targeting PBPs other than PBP2 in Enterobacteriaceae
Combined with other compounds: Yes
Description: Synthetic compound; combination of beta-lactam and diazabicyclooctane beta-lactamase inhibitor
Institute where first reported: Meiji Seika Pharma and Fedora Pharmaceuticals; Antimicrobial Resistance and Healthcare Associated Infections Reference Unit, Public Health England, London, UK
Year first mentioned: 2015
Highest developmental phase: Phase 3 (NCT05887908)
Development status: Active as of 2024
Chemical structure(s):
Nacubactam
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Molecular weight: 324.31
Iso. SMILES: C1C[C@H](N2C[C@@H]1N(C2=O)OS(=O)(=O)O)C(=O)NOCCN
InChI Key: RSBPYSTVZQAADE-RQJHMYQMSA-N
Can. SMILES: C1C[C@@H](C(=O)NOCCN)N2C[C@@H]1N(C2=O)OS(=O)(=O)O
InChI: InChI=1S/C9H16N4O7S/c10-3-4-19-11-8(14)7-2-1-6-5-12(7)9(15)13(6)20-21(16,17)18/h6-7H,1-5,10H2,(H,11,14)(H,16,17,18)/t6-,7+/m1/s1
Aztreonam
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Molecular weight: 435.44
Iso. SMILES: C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)NC(=O)/C(=N\OC(C)(C)C(=O)O)/C2=CSC(=N2)N
InChI Key: WZPBZJONDBGPKJ-VEHQQRBSSA-N
Can. SMILES: C[C@H]1[C@@H](C(=O)N1S(=O)(=O)O)NC(=O)/C(=N\OC(C)(C)C(=O)O)/C2=CSC(=N2)N
InChI: InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5742832
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/73386748
Citation: https://academic.oup.com/jac/article/70/11/3032/2364032?login=true

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