U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PIRAZMONAM SODIUM

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

HIDE SMILES / InChI

Molecular Formula C22H22N10O12S2
Molecular Weight 682.6
Charge -2
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
The new monobactams: chemistry and biology.
1988 Feb
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:26:47 GMT 2023
Edited
by admin
on Fri Dec 15 16:26:47 GMT 2023
Record UNII
M89TPX4O2C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRAZMONAM SODIUM
USAN  
USAN  
Official Name English
PIRAZMONAM SODIUM [USAN]
Common Name English
SQ-83360
Code 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-, SODIUM SALT (1:2)
Systematic 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-, DISODIUM SALT
Common Name English
2-[[[(2-Amino-4-thiazolyl)[[1-[[[3-(1,4-dihydro-5-hydroxy-4-oxopicolinamido)-2-oxo-1-imidazolidinyl]sulfonyl]carbamoyl]-2-oxo-3-azetidinyl]carbamoyl]methylene]amino]oxy]-2-methylpropionic acid, disodium salt
Systematic Name English
SQ 83360
Code English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 16:26:47 GMT 2023 , Edited by admin on Fri Dec 15 16:26:47 GMT 2023
Code System Code Type Description
USAN
Y-94
Created by admin on Fri Dec 15 16:26:47 GMT 2023 , Edited by admin on Fri Dec 15 16:26:47 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110757
Created by admin on Fri Dec 15 16:26:47 GMT 2023 , Edited by admin on Fri Dec 15 16:26:47 GMT 2023
PRIMARY
NCI_THESAURUS
C76564
Created by admin on Fri Dec 15 16:26:47 GMT 2023 , Edited by admin on Fri Dec 15 16:26:47 GMT 2023
PRIMARY
CAS
104393-00-2
Created by admin on Fri Dec 15 16:26:47 GMT 2023 , Edited by admin on Fri Dec 15 16:26:47 GMT 2023
PRIMARY
FDA UNII
M89TPX4O2C
Created by admin on Fri Dec 15 16:26:47 GMT 2023 , Edited by admin on Fri Dec 15 16:26:47 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY