Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H22N10O12S2.2Na |
Molecular Weight | 728.579 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[Na+].CC(C)(O\N=C(/C(=O)NC1CN(C(=O)[N-]S(=O)(=O)N2CCN(NC(=O)C3=CC(=O)C(O)=CN3)C2=O)C1=O)C4=CSC(N)=N4)C([O-])=O
InChI
InChIKey=KXHDKHNHRIULTC-UHFFFAOYSA-L
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;;/h5-6,8,10H,3-4,7H2,1-2H3,(H8,23,24,25,26,27,28,29,33,34,35,36,38,39,40);;/q;2*+1/p-2
Pirazmonam is a potent anti-gram-negative monobactam that is differentiated from aztreonam by its high intrinsic activity against Ps. aeruginosa and good activity against Pseudomonas species. Pirazmonam has generally poor activity against gram-positive aerobic bacteria and anaerobic bacteria. Pirazmonam is a Trojan Horse molecule containing a b-lactam antibiotic that has been developed based on bacterial iron uptake systems. It features high structural similarity to aztreonam attached to a 3-hydroxy-4-pyridinone iron chelating group. Pirazmonam exhibited strong affinity to penicillin-binding protein 3 (PBP3) of Escherichia coli and moderate to negligible affinity to the other E. coli PBPs.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
The new monobactams: chemistry and biology. | 1988 Feb |
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Cir and Fiu proteins in the outer membrane of Escherichia coli catalyze transport of monomeric catechols: study with beta-lactam antibiotics containing catechol and analogous groups. | 1990 Mar |
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In vitro antibacterial activity and interactions with beta-lactamases and penicillin-binding proteins of the new monocarbam antibiotic U-78608. | 1990 May |
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Characterization of the aqueous iron(III) chelation chemistry of a potential Trojan Horse antimicrobial agent: chelate structure, stability and pH dependent speciation. | 2012 Oct |
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C260
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CHEMBL2110757
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C76564
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104393-00-2
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M89TPX4O2C
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ACTIVE MOIETY
SUBSTANCE RECORD