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Showing drug card for Tazobactam (DB01606)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:08
Primary Accession Number DB01606
Secondary Accession Number
  • EXPT03012
Name Tazobactam
Drug Type
  • Approved
  • Small Molecule
Description Tazobactam is a antibacterial penicillin derivative which inhibits the action of bacterial beta-lactamases.
Synonyms Not Available
Brand Names Not Available
Brand Mixtures
  1. Tazocin (Tazobactam + Piperacillin)
  2. Zosyn (Tazobactam + Piperacillin)
Chemical IUPAC Name (2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Chemical Formula C10H12N4O5S
Chemical Structure Structure
CAS Registry Number 89786-04-9
InChI Identifier InChI=1/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/f/h16H
InChI Key LPQZKKCYTLCDGQ-OIUVGDJLDS
KEGG Drug D00660 Link Image
KEGG Compound C07771 Link Image
PubChem Compound 123630 Link Image
PubChem Substance 10240806 Link Image
ChEBI ID Not Available
PharmGKB ID PA451592 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02170795 Link Image
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Tazobactam Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 300.2910
Monoisotopic Molecular Weight 300.0528
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 9.59e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP -1.80 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -1.50 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1VM1 Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES C[C@]1(CN2C=CN=N2)[C@@H](N2[C@@H](CC2=O)S1(=O)=O)C(O)=O
Canonical SMILES CC1(CN2C=CN=N2)C(N2C(CC2=O)S1(=O)=O)C(O)=O
Drug Category
  • Enzyme Inhibitors
ATC Codes Not Available
AHFS Codes Not Available
Indication Used in combination with piperacillin to broaden the spectrum of piperacillin antibacterial action.
Pharmacology Tazobactam is a compound which inhibits the action of bacterial beta-lactamases. It is added to the extended spectrum beta-lactam antibiotic piperacillin.
Mechanism of Action Tazobactam broadens the spectrum of piperacillin by making it effective against organisms that express beta-lactamase and would normally degrade piperacillin.
Absorption Not Available
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Beta-lactamase SHV-1 precursor
Drug Target 1 [top]
Target 1 ID 3687
Target 1 Name Beta-lactamase SHV-1 precursor
Target 1 Synonyms
  1. EC 3.5.2.6
  2. PIT-2
Target 1 Gene Name bla
Target 1 Protein Sequence >Beta-lactamase SHV-1 precursor 
MRYIRLCIISLLATLPLAVHASPQPLEQIKLSESQLSGRVGMIEMDLASGRTLTAWRADE
RFPMMSTFKVVLCGAVLARVDAGDEQLERKIHYRQQDLVDYSPVSEKHLADGMTVGELCA
AAITMSDNSAANLLLATVGGPAGLTAFLRQIGDNVTRLDRWETELNEALPGDARDTTTPA
SMAATLRKLLTSQRLSARSQRQLLQWMVDDRVAGPLIRSVLPAGWFIADKTGAGERGARG
IVALLGPNNKAERIVVIYLRDTPASMAERNQQIAGIGAALIEHWQR
Target 1 Number of Residues 290
Target 1 Molecular Weight 31224
Target 1 Theoretical pI 8.08
Target 1 GO Classification
Function
catalytic activity
hydrolase activity
hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds
hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in cyclic amides
beta-lactamase activity
Process
physiological process
metabolism
cellular metabolism
drug metabolism
antibiotic metabolism
antibiotic catabolism
beta-lactam antibiotic catabolism
response to stimulus
response to abiotic stimulus
response to chemical stimulus
response to drug
response to antibiotic
Component
Not Available
Target 1 General Function Defense mechanisms
Target 1 Specific Function A beta-lactam + H(2)O = a substituted beta- amino acid
Target 1 Pathways
Name SMPDB Link KEGG Link
Penicillins and cephalosporins biosynthesis map00311 Link Image
Target 1 Reactions
  • A beta-lactam + H2O = a substituted beta-amino acid
Target 1 Pfam Domain Function
Target 1 Signals
  • 1-21
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 5002312 Link Image
Target 1 UniProtKB/Swiss-Prot ID P0AD63 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name BLA1_ECOLI Link Image
Target 1 PDB ID 1Q2P Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cytoplasmic
Target 1 Gene Sequence >861 bp 
ATGCGTTATATTCGCCTGTGTATTATCTCCCTGTTAGCCACCCTGCCGCTGGCGGTACAC
GCCAGCCCGCAGCCGCTTGAGCAAATTAAACTAAGCGAAAGCCAGCTGTCGGGCCGCGTA
GGCATGATAGAAATGGATCTGGCCAGCGGCCGCACGCTGACCGCCTGGCGCGCCGATGAA
CGCTTTCCCATGATGAGCACCTTTAAAGTAGTGCTCTGCGGCGCAGTGCTGGCGCGGGTG
GATGCCGGTGACGAACAGCTGGAGCGAAAGATCCACTATCGCCAGCAGGATCTGGTGGAC
TACTCGCCGGTCAGCGAAAAACACCTTGCCGACGGCATGACGGTCGGCGAACTCTGCGCC
GCCGCCATTACCATGAGCGATAACAGCGCCGCCAATCTGCTACTGGCCACCGTCGGCGGC
CCCGCAGGATTGACTGCCTTTTTGCGCCAGATCGGCGACAACGTCACCCGCCTTGACCGC
TGGGAAACGGAACTGAATGAGGCGCTTCCCGGCGACGCCCGCGACACCACTACCCCGGCC
AGCATGGCCGCGACCCTGCGCAAGCTGCTGACCAGCCAGCGTCTGAGCGCCCGTTCGCAA
CGGCAGCTGCTGCAGTGGATGGTGGACGATCGGGTCGCCGGACCGTTGATCCGCTCCGTG
CTGCCGGCGGGCTGGTTTATCGCCGATAAGACCGGAGCTGGCGAGCGGGGTGCGCGCGGG
ATTGTCGCCCTGCTTGGCCCGAATAACAAAGCAGAGCGCATTGTGGTGATTTATCTGCGG
GATACCCCGGCGAGCATGGCCGAGCGAAATCAGCAAATCGCCGGGATCGGCGCGGCGCTG
ATCGAGCACTGGCAACGCTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Barthelemy M, Peduzzi J, Labia R: Complete amino acid sequence of p453-plasmid-mediated PIT-2 beta-lactamase (SHV-1). Biochem J. 1988 Apr 1;251(1):73-9. [PubMed Link Image]
  2. Barthelemy M, Peduzzi J, Labia R: N-terminal amino acid sequence of PIT-2 beta-lactamase (SHV-1) J Antimicrob Chemother. 1987 Jun;19(6):839-41. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.