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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2019-07-23 05:59:58 UTC
HMDB IDHMDB0014499
Secondary Accession Numbers
  • HMDB14499
Metabolite Identification
Common NameAztreonam
DescriptionAztreonam is only found in individuals that have used or taken this drug. It is a 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. [PubChem]The bactericidal action of aztreonam results from the inhibition of bacterial cell wall synthesis due to a high affinity of aztreonam for penicillin binding protein 3 (PBP3). By binding to PBP3, aztreonam inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. It is possible that aztreonam interferes with an autolysin inhibitor.
Structure
Data?1563861598
Synonyms
ValueSource
(Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acidChEBI
AzactamChEBI
AZTChEBI
AztreonamumChEBI
PrimbactamChEBI
MonobactamKegg
(Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionateGenerator
(Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulphO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionateGenerator
(Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulphO-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acidGenerator
Az threonamHMDB
Aztreonam esteve brandHMDB
Bristol myers squibb brand OF aztreonamHMDB
Az-threonamHMDB
Esteve brand OF aztreonamHMDB
Sanofi winthrop brand OF aztreonamHMDB
Squibb brand OF aztreonamHMDB
AzthreonamHMDB
Aztreonam squibb brandHMDB
Bristol-myers squibb brand OF aztreonamHMDB
UrobactamHMDB
Chemical FormulaC13H17N5O8S2
Average Molecular Weight435.433
Monoisotopic Molecular Weight435.051853925
IUPAC Name2-{[(Z)-[(2-amino-1,3-thiazol-4-yl)({[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]carbamoyl})methylidene]amino]oxy}-2-methylpropanoic acid
Traditional Nameaztreonam
CAS Registry Number78110-38-0
SMILES
[H]OC(=O)C(O\N=C(/C(=O)N([H])[C@]1([H])C(=O)N([C@@]1([H])C([H])([H])[H])S(=O)(=O)O[H])C1=C([H])SC(=N1)N([H])[H])(C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1
InChI KeyWZPBZJONDBGPKJ-VEHQQRBSSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monobactams. Monobactams are compounds comprising beta-lactam ring is alone and not fused to another ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentMonobactams
Alternative Parents
Substituents
  • Monobactam
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 2,4-disubstituted 1,3-thiazole
  • 1,3-thiazol-2-amine
  • Organic sulfuric acid or derivatives
  • Azole
  • Heteroaromatic compound
  • Thiazole
  • Amino acid or derivatives
  • Azetidine
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organic zwitterion
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.043 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.043 g/LALOGPS
logP0.01ALOGPS
logP-1.9ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)4.14ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area201.58 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity92.99 m³·mol⁻¹ChemAxon
Polarizability39.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-9425200000-e19e767dba01d637f0c9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9502400000-63d4b17051748b65ae9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-7519400000-58625f5f40c4248abff6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02dj-6719200000-9dc50bd4db5ecbf70545Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9510000000-60df6cd78d995652b92fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9335700000-1188040f3c9d08230a28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0729-1494000000-a113d31838979a9528a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9500000000-25bbcb89ddb9d4f2c253Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00355 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00355 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00355
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4674940
KEGG Compound IDC06840
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAztreonam
METLIN IDNot Available
PubChem Compound5742832
PDB IDNot Available
ChEBI ID161680
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available