DrugBank: Tazobactam (DB01606)

targets (2)

Identification

Name

Tazobactam

Accession Number

DB01606 (EXPT03012)

Type

small molecule

Groups

approved

Description

Tazobactam is a antibacterial penicillin derivative which inhibits the action of bacterial beta-lactamases.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Brand names

Not Available

Brand name mixtures

Tazocin (Tazobactam + Piperacillin)
Zosyn (Tazobactam + Piperacillin)

Categories

Enzyme Inhibitors

CAS number

89786-04-9

Weight

Average: 300.291
Monoisotopic: 300.052840204

Chemical Formula

C₁₀H₁₂N₄O₅S

InChI Key

InChIKey=LPQZKKCYTLCDGQ-WEDXCCLWSA-N

InChI

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

Plain Text

IUPAC Name

(2S,3S,5R)-3-methyl-4,4,7-trioxo-3-(1H-1,2,3-triazol-1-ylmethyl)-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

SMILES

[H][C@@]12CC(=O)N1[C@@H](C(O)=O)[C@](C)(CN1C=CN=N1)S2(=O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Thiazolidines
Penicillins

Substructures

Hydroxy Compounds
Acetates
Amino Ketones
Triazoles
Sulfonyls
Aliphatic and Aryl Amines
Carboxylic Acids and Derivatives
Beta Lactams
Sulfones
Thiazoles
Heterocyclic compounds
Aromatic compounds
Carboxamides and Derivatives
Lactams
Azetidines
Thiazolidines
Sulfoxides
Penicillins

Pharmacology

Indication

Used in combination with piperacillin to broaden the spectrum of piperacillin antibacterial action.

Pharmacodynamics

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

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	9.59e+00 g/l	ALOGPS
logP	-1.80	ALOGPS
logP	-1.40	ChemAxon Molconvert
logS	-1.50	ALOGPS
pKa	18.64	ChemAxon Molconvert
hydrogen acceptor count	7	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	122.46	ChemAxon Molconvert
rotatable bond count	3	ChemAxon Molconvert
refractivity	74.82	ChemAxon Molconvert
polarizability	26.22	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00660
KEGG Compound	C07771
PubChem Compound	123630
PubChem Substance	46508088
ChemSpider	110216
BindingDB	50053173
Therapeutic Targets Database	DAP000926
PharmGKB	PA451592
Drug Product Database	2170795
Wikipedia	http://en.wikipedia.org/wiki/Tazobactam

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1VM1

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Beta-lactamase SHV-1 precursor Pharmacological action: unknown Actions: inhibitor A beta-lactam + H(2)O = a substituted beta- amino acid Organism class: bacterial UniProt ID: P0AD63 Gene: bla Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 2. Beta-lactamase TEM Pharmacological action: yes Actions: inhibitor TEM-type are the most prevalent beta-lactamases in enterobacteria; they hydrolyze the beta-lactam bond in susceptible beta-lactam antibiotics, thus conferring resistance to penicillins and cephalosporins Organism class: bacterial UniProt ID: P62594 Gene: bla Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Yang Y, Rasmussen BA, Shlaes DM: Class A beta-lactamases—enzyme-inhibitor interactions and resistance. Pharmacol Ther. 1999 Aug;83(2):141-51. Pubmed

Targets

1. Beta-lactamase SHV-1 precursor

Pharmacological action: unknown
Actions: inhibitor

A beta-lactam + H(2)O = a substituted beta- amino acid

Organism class: bacterial
UniProt ID: P0AD63 Link_out

Gene: bla
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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

2. Beta-lactamase TEM

Pharmacological action: yes
Actions: inhibitor

TEM-type are the most prevalent beta-lactamases in enterobacteria; they hydrolyze the beta-lactam bond in susceptible beta-lactam antibiotics, thus conferring resistance to penicillins and cephalosporins

Organism class: bacterial
UniProt ID: P62594 Link_out

Gene: bla
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Yang Y, Rasmussen BA, Shlaes DM: Class A beta-lactamases—enzyme-inhibitor interactions and resistance. Pharmacol Ther. 1999 Aug;83(2):141-51. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:50

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.