PIRAZMONAM

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2193625 | https://www.ncbi.nlm.nih.gov/pubmed/3360965 | https://www.ncbi.nlm.nih.gov/pubmed/22855208 | Milne, G.W.A. (2018) Drugs: Synonyms and Properties, retrieved from: https://books.google.ru/books?id=xUlaDwAAQBAJ

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	3360965
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	2407721
In vitro antibacterial activity and interactions with beta-lactamases and penicillin-binding proteins of the new monocarbam antibiotic U-78608.	1990 May	2193625
Characterization of the aqueous iron(III) chelation chemistry of a potential Trojan Horse antimicrobial agent: chelate structure, stability and pH dependent speciation.	2012 Oct	22855208

Name

Type

Language

PIRAZMONAM

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