Details
Stereochemistry | RACEMIC |
Molecular Formula | C22H24N10O12S2 |
Molecular Weight | 684.616 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)(O\N=C(/C(=O)NC1CN(C(=O)NS(=O)(=O)N2CCN(NC(=O)C3=CC(=O)C(O)=CN3)C2=O)C1=O)C4=CSC(N)=N4)C(O)=O
InChI
InChIKey=JXSPWQGYERHATM-MUXKCCDJSA-N
InChI=1S/C22H24N10O12S2/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)/b28-14-
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
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NCI_THESAURUS |
C260
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1S3Z442A8N
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C76563
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CHEMBL2110757
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100000081659
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108319-07-9
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6206
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DTXSID00883178
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6328646
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SUB09896MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)