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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-09-27 08:27:35 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
Thumb
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
AztreonamumChEBI
PrimbactamChEBI
(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
AZTHMDB
Az threonamMeSH
Aztreonam esteve brandMeSH
Bristol myers squibb brand OF aztreonamMeSH
Az-threonamMeSH
Esteve brand OF aztreonamMeSH
Sanofi winthrop brand OF aztreonamMeSH
Squibb brand OF aztreonamMeSH
AzthreonamMeSH
Aztreonam squibb brandMeSH
Bristol-myers squibb brand OF aztreonamMeSH
UrobactamMeSH
Chemical FormulaC13H17N5O8S2
Average Molecular Weight435.433
Monoisotopic Molecular Weight435.051853925
IUPAC Name(2S,3S)-3-[(2Z)-2-(2-azaniumyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate
Traditional Nameaztreonam
CAS Registry Number78110-38-0
SMILES
C[C@H]1[C@H](NC(=O)C(=N/OC(C)(C)C(=O)O)\C2=CSC([NH3+])=N2)C(=O)N1S([O-])(=O)=O
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
DescriptionThis compound belongs to the class of organic compounds known as monobactams. These 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:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

    Antimicrobial agent:

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
logP0.04ALOGPS
logP-3.1ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)4.14ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area206.03 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity102.09 m³·mol⁻¹ChemAxon
Polarizability39.94 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-9425200000-e19e767dba01d637f0c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00du-9502400000-63d4b17051748b65ae9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-7519400000-58625f5f40c4248abff6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02dj-6719200000-9dc50bd4db5ecbf70545View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006w-9510000000-60df6cd78d995652b92fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9335700000-1188040f3c9d08230a28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0729-1494000000-a113d31838979a9528a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9500000000-25bbcb89ddb9d4f2c253View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available