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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:45 UTC
HMDB IDHMDB14499
Secondary Accession NumbersNone
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
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 KeyInChIKey=WZPBZJONDBGPKJ-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
  • 2,4-disubstituted 1,3-thiazole
  • Heteroaromatic compound
  • Thiazole
  • Organic sulfuric acid or derivatives
  • Azole
  • Secondary carboxylic acid amide
  • Oxime ether
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Bacterial Agents
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.29e-02 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.043 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity102.09 m3·mol-1ChemAxon
Polarizability39.94 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00355
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00355
  • Not Applicable
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
NuGOwiki LinkHMDB14499
Metagene LinkHMDB14499
METLIN IDNot Available
PubChem Compound5742832
PDB IDNot Available
ChEBI ID161680
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available