AZR

2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl)-2-oxo-2-{[(2S,3S)-1-oxo-3-(sulfoamino)butan-2-yl]amino}ethylidene]amino}oxy)-2-methylpropanoic acid


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Chemical Component Summary

Name2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl)-2-oxo-2-{[(2S,3S)-1-oxo-3-(sulfoamino)butan-2-yl]amino}ethylidene]amino}oxy)-2-methylpropanoic acid
SynonymsAZTREONAM, open form
Identifiers2-[(Z)-[1-(2-azanyl-1,3-thiazol-4-yl)-2-oxidanylidene-2-[[(2S,3S)-1-oxidanylidene-3-(sulfoamino)butan-2-yl]amino]ethylidene]amino]oxy-2-methyl-propanoic acid
FormulaC13 H19 N5 O8 S2
Molecular Weight437.449
TypeNON-POLYMER
Isomeric SMILESC[C@@H]([C@@H](C=O)NC(=O)/C(=N\OC(C)(C)C(=O)O)/c1csc(n1)N)NS(=O)(=O)O
InChIInChI=1S/C13H19N5O8S2/c1-6(18-28(23,24)25)7(4-19)15-10(20)9(8-5-27-12(14)16-8)17-26-13(2,3)11(21)22/h4-7,18H,1-3H3,(H2,14,16)(H,15,20)(H,21,22)(H,23,24,25)/b17-9-/t6-,7+/m0/s1
InChIKeyOEVQTUTXOVDNJO-GEEOIBTQSA-N

Chemical Details

Formal Charge0
Atom Count47
Chiral Atom Count2
Bond Count47
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB00355 
NameAztreonam
Groups approved
DescriptionA monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms.
Synonyms
  • Aztréonam
  • Aztreonam lysine
  • Aztreonam
  • (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid
  • 2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl) -2- {[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino} -2- oxoethylidene]amino}oxy)-2-methylpropanoic acid
Brand Names
  • Aztreonam
  • Azactam
  • Cayston
IndicationFor the treatment of the following infections caused by susceptible gram-negative microorganisms: urinary tract infections, lower respiratory tract infections, septicemia, skin and skin-structure infections, intra-abdominal infections, and gynecologic infections.
Categories
  • Amides
  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterials for Systemic Use
  • Antiinfectives for Systemic Use
ATC-CodeJ01DF01
CAS number78110-38-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Penicillin-binding protein 3MLKKCILLVFLCVGLIGLIGCSKTDSPEDRMEAFVKQWNDQQFDDMYQSL...unknowninhibitor
Beta-lactamaseMMKKSICCALLLTASFSTFAAAKTEQQIADIVNRTITPLMQEQAIPGMAV...unknownpotentiator
Beta-lactamase Toho-1MMTQSIRRSMLTVMATLPLLFSSATLHAQANSVQQQLEALEKSSGGRLGV...unknownsubstrate
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 9600402