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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:48 UTC
HMDB IDHMDB0015544
Secondary Accession Numbers
  • HMDB15544
Metabolite Identification
Common NameTazobactam
DescriptionTazobactam, also known as YTR 830, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. In simple terms, it is an ingredient that can be added to certain antibiotics to make them less vulnerable to bacteria's antimicrobial resistance. Tazobactam is a drug. Tazobactam is an extremely weak basic (essentially neutral) compound (based on its pKa). It is commonly used as its sodium salt, tazobactam sodium. Tazobactam is a heavily modified penicillin and a sulfone. Tazobactam broadens the spectrum of piperacillin by making it effective against organisms that express β-lactamase and would normally degrade piperacillin. Tazobactam is a pharmaceutical drug that inhibits the action of bacterial β-lactamases, especially those belonging to the SHV-1 and TEM groups. Tazobactam is combined with the extended spectrum β-lactam antibiotic piperacillin in the drug piperacillin/tazobactam, used in infections due Pseudomonas aeruginosa. Tazobactam was patented in 1982 and came into medical use in 1992.
Structure
Data?1582753308
Synonyms
ValueSource
(2S,3S,5S)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxideChEBI
TazobactamumChEBI
(2S,3S,5S)-3-Methyl-7-oxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxideGenerator
YTR 830HMDB
YTR 830HHMDB
Taszobactam sodiumHMDB
YTR-830HMDB
Tazobactam sodiumMeSH
Chemical FormulaC10H12N4O5S
Average Molecular Weight300.291
Monoisotopic Molecular Weight300.052840204
IUPAC Name(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional Nametazobactam
CAS Registry Number89786-04-9
SMILES
[H][C@@]12CC(=O)N1[C@@H](C(O)=O)[C@](C)(CN1C=CN=N1)S2(=O)=O
InChI Identifier
InChI=1S/C10H12N4O5S/c1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19/h2-3,7-8H,4-5H2,1H3,(H,16,17)/t7-,8+,10+/m1/s1
InChI KeyLPQZKKCYTLCDGQ-WEDXCCLWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Penam
  • Azole
  • Beta-lactam
  • Sulfone
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Thiazolidine
  • 1,2,3-triazole
  • Azetidine
  • Carboxamide group
  • Lactam
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility9.59 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.59 g/LALOGPS
logP-1.8ALOGPS
logP-1.4ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
pKa (Strongest Basic)0.73ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area122.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.82 m³·mol⁻¹ChemAxon
Polarizability26.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05ox-9600000000-54f1ff15fea55805a4c4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9621000000-bc21d0c2147bde679308Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-9080000000-84419d5374d8976b5452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1091000000-e00f9ea85b1daaf20953Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9370000000-2e9deb92fe8e2364417aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-9150000000-d4179daa6a2c7403e1e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-9380000000-ae0f16462e209d76b09bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9400000000-53574c9e07bfecfd0557Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01606 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01606 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01606
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID110216
KEGG Compound IDC07771
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTazobactam
METLIN IDNot Available
PubChem Compound123630
PDB IDNot Available
ChEBI ID9421
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available