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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
Structure of PIRAZMONAM

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-

HIDE SMILES / InChI
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

PubMed

TitleDatePubMed
Characterization of the aqueous iron(III) chelation chemistry of a potential Trojan Horse antimicrobial agent: chelate structure, stability and pH dependent speciation.
2012 Oct
Name Type Language
PIRAZMONAM
INN  
INN  
Official Name English
PROPANOIC ACID, 2-(((1-(2-AMINO-4-THIAZOLYL)-2-((1-((((3-(((1,4-DIHYDRO-5-HYDROXY-4-OXO-2-PYRIDINYL)CARBONYL)AMINO)-2-OXO-1-IMIDAZOLIDINYL)SULFONYL)AMINO)CARBONYL)-2-OXO-3-AZETIDINYL)AMINO)-2-OXOETHYLIDENE)AMINO)OXY)-2-METHYL-
Common Name English
pirazmonam [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
Code System Code Type Description
FDA UNII
1S3Z442A8N
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
NCI_THESAURUS
C76563
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110757
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
SMS_ID
100000081659
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
CAS
108319-07-9
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
INN
6206
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID00883178
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
PUBCHEM
6328646
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY
EVMPD
SUB09896MIG
Created by admin on Fri Dec 15 16:37:06 GMT 2023 , Edited by admin on Fri Dec 15 16:37:06 GMT 2023
PRIMARY