Compound ID | 151

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BAL30072

Class: Beta-lactam

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Cell wall synthesis inhibitor
Target Pathogen: Active against multidrug resistant Gram-negative infections
Propensity to select resistant mutants: No (demonstrated high resistance)
Description: A siderophore-sulfactam
Institute where first reported: Basilea Pharmaceutica, Switzerland
Year first mentioned: 2008
Highest development stage: Phase 1
Development status: Withdrawn
Reason dropped: Liver injury detected 3-days post treatment (iv formulation); preclinical studies of inhalation also terminated due to 'lack of confidence in candidate's success'
Chemical structure(s):
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Molecular weight: 518.48
Iso. SMILES: CC1([C@@H](C(=O)N1OS(=O)(=O)O)NC(=O)/C(=N\OCC2=CC(=O)C(=CN2O)O)/C3=CSC(=N3)N)C
InChI Key: KLFSEZJCLYBFKQ-WXYNYTDUSA-N
Can. SMILES: CC1(C)[C@@H](C(=O)N1OS(=O)(=O)O)NC(=O)/C(=N\OCC2=CC(=O)C(=CN2O)O)/C3=CSC(=N3)N
InChI: InChI=1S/C16H18N6O10S2/c1-16(2)12(14(26)22(16)32-34(28,29)30)19-13(25)11(8-6-33-15(17)18-8)20-31-5-7-3-9(23)10(24)4-21(7)27/h3-4,6,12,24,27H,5H2,1-2H3,(H2,17,18)(H,19,25)(H,28,29,30)/b20-11-/t12-/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/52942440
Guide to Pharmacology: BAL30072
Citations:
  • http://aac.asm.org/content/57/5/2095.full
  • https://www.escmid.org/escmid_publications/escmid_elibrary/?q=bal30072&id=2173&L=0&x=0&y=0
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3058568/
  • https://www.basilea.com/fileadmin/user_upload/pressreleases/766305-en-708837.pdf?v=1546612716

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