Compound ID | 1122

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Tigemonam

Synonym(s): SQ-30213  |  SQ30213  |  SQ-30836 (tigemonam dicholate)  |  SQ30836

Class: Beta-lactam

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-positive & Gram-negative
Mechanism of action: Cell wall synthesis inhibitor. Binds penicillin-binding proteins, including PBP1a and PBP3 in E. coli, inhibiting peptidoglycan synthesis and producing bactericidal activity.
Target Pathogen: Escherichia coli, Klebsiella spp., Enterobacter spp., Citrobacter spp., Proteus spp., Providencia spp., Salmonella spp., Shigella spp., Serratia spp., Yersinia enterocolitica, Aeromonas hydrophila, Haemophilus spp., Neisseria spp., Moraxella/Branhamella catarrhalis, and limited activity against some Streptococcus spp.
Propensity to select resistant mutants: Yes
Description: Synthetic orally active monobactam antibacterial with potent activity against Enterobacteriaceae and other aerobic Gram-negative bacteria; development was discontinued during pipeline reprioritisation following the Squibb–Bristol-Myers merger.
Institute where first reported: E. R. Squibb & Sons / Squibb Institute for Medical Research, Princeton, USA
Year first mentioned: 1985
Highest development stage: Phase 2
Development status: Inactive
Reason dropped: Clinical development discontinued in 1989. No safety, efficacy, or environmental risks were disclosed.
Chemical structure(s):
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Molecular weight: 437.41
Iso. SMILES: CC1([C@@H](C(=O)N1OS(=O)(=O)O)NC(=O)/C(=N\OCC(=O)O)/C2=CSC(=N2)N)C
InChI Key: VAMSVIZLXJOLHZ-QWFSEIHXSA-N
Can. SMILES: CC1(C)[C@@H](C(=O)N1OS(=O)(=O)O)NC(=O)/C(=N\OCC(=O)O)/C2=CSC(=N2)N
InChI: InChI=1S/C12H15N5O9S2/c1-12(2)8(10(21)17(12)26-28(22,23)24)15-9(20)7(16-25-3-6(18)19)5-4-27-11(13)14-5/h4,8H,3H2,1-2H3,(H2,13,14)(H,15,20)(H,18,19)(H,22,23,24)/b16-7-/t8-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/9576769
Guide to Pharmacology: tigemonam
Citations:
  • https://doi.org/10.7164/antibiotics.38.1536
  • https://doi.org/10.1128/aac.31.2.219
  • https://doi.org/10.1128/aac.31.2.226
  • https://doi.org/10.1093/jac/24.2.173
  • https://doi.org/10.1080/1120009X.1989.11738942
  • https://doi.org/10.1128/aac.32.1.84
    • Patents:
  • US20140128364A1
  • US4638061A
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