Compound ID | 628

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Pirazmonam

Synonym(s): SQ 83,360

Class: Beta-lactam (monocarbam, siderophore monobactam)

Spectrum of activity: Gram-negative
Details of activity: Generally poor activity against Gram positive aerobes and anaerobes (1) Excellent activity against gram - organisms including Pseudomonas and Acinetobacter.
Description: Breuer, H., et al. "Structure-activity relationships among sulfonylaminocarbonyl activated monobactams leading to SQ-83,360." Program and Abstracts of the 25th Intersci. Conf. on Antimicrob. Agents Chemother. No. 371.
Institute where first reported: Squibb Institute, USA
Year first mentioned: 1985
Highest developmental phase: Preclinical
Development status: Inactive
Reason Dropped: Resistance issues (JS)
Chemical structure(s):
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Molecular weight: 728.58
Iso. SMILES: CC(C)(C(=O)[O-])O/N=C(/C1=CSC(=N1)N)\C(=O)NC2CN(C2=O)/C(=N/S(=O)(=O)N3CCN(C3=O)NC(=O)C4=CC(=O)C(=CN4)O)/[O-].[Na+].[Na+]
InChI Key: WGJXEHGALNGLAS-LDZIOWNMSA-L
Can. SMILES: CC(C)(C(=O)[O-])O/N=C(/C1=CSC(=N1)N)\C(=O)NC2CN(C2=O)/C(=N/S(=O)(=O)N3CCN(C3=O)NC(=O)C4=CC(=O)C(=CN4)O)/[O-].[Na+].[Na+]
InChI: InChI=1S/C22H24N10O12S2.2Na/c1-22(2,18(38)39)44-28-14(11-8-45-19(23)26-11)16(36)25-10-7-30(17(10)37)20(40)29-46(42,43)32-4-3-31(21(32)41)27-15(35)9-5-12(33)13(34)6-24-9;;/h5-6,8,10,34H,3-4,7H2,1-2H3,(H2,23,26)(H,24,33)(H,25,36)(H,27,35)(H,29,40)(H,38,39);;/q;2*+1/p-2/b28-14-;;
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/91668151
Guide to Pharmacology: pirazmonam
Citations:
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC171711/
  • http://www.ncbi.nlm.nih.gov/pmc/articles/PMC192042/

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