You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameTazobactam
Accession NumberDB01606  (EXPT03012)
TypeSmall Molecule
GroupsApproved
Description

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

Structure
Thumb
Synonyms
CL-298741
Tazobactam
YTR-830H
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Jamp-pip/tazJamp Pharma Corporation
Mylan-piperacillin and Tazobactam for InjectionMylan Pharmaceuticals Ulc
Piperacillin / Tazobactam Powder for InjectionTeva Canada Limited
Piperacillin and TazobactamHospira, Inc
Piperacillin and Tazobactam for InjectionApotex Inc
Piperacillin Sodium/tazobactam Sodium Powder for InjectionSandoz Canada Incorporated
Piperacillin, TazobactamSagent Pharmaceuticals
Piperacillin/tazobactam for InjectionPharma Strides Canada Corporation
TazocinPfizer Canada Inc
Tazocin Pws IV 2g Piperacillin-.25g Tazobac.Lederle Cyanamid Canada Inc.
Tazocin Pws IV 3g Piperacillin-.375g TazobacLederle Cyanamid Canada Inc.
Tazocin Pws IV 4g Piperacillin-.5g Tazobac.Lederle Cyanamid Canada Inc.
Vpi-piperacillin and Tazobactam for InjectionVpi Pharmaceuticals Inc
ZerbaxaMerck Sharp & Dohme Corp.
ZosynWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Zosyn In Galaxy ContainersWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Zosyn Pharmacy Bulk PackageWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.
Salts
Name/CASStructureProperties
Tazobactam sodium
ThumbNot applicableDBSALT001475
Categories
UNIISE10G96M8W
CAS number89786-04-9
WeightAverage: 300.291
Monoisotopic: 300.052840204
Chemical FormulaC10H12N4O5S
InChI KeyInChIKey=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
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
SMILES
[H][C@@]12CC(=O)N1[C@@H](C(O)=O)[C@](C)(CN1C=CN=N1)S2(=O)=O
Taxonomy
DescriptionThis compound 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
  • Heteroaromatic compound
  • 1,2,3-triazole
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Sulfone
  • Beta-lactam
  • Azole
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in combination with piperacillin to broaden the spectrum of piperacillin antibacterial action.
PharmacodynamicsTazobactam is a compound which inhibits the action of bacterial beta-lactamases. It is added to the extended spectrum beta-lactam antibiotic piperacillin.
Mechanism of actionTazobactam broadens the spectrum of piperacillin by making it effective against organisms that express beta-lactamase and would normally degrade piperacillin.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6161
Blood Brain Barrier-0.9659
Caco-2 permeable-0.6156
P-glycoprotein substrateNon-substrate0.5351
P-glycoprotein inhibitor INon-inhibitor0.8574
P-glycoprotein inhibitor IINon-inhibitor0.9917
Renal organic cation transporterNon-inhibitor0.8432
CYP450 2C9 substrateNon-substrate0.6516
CYP450 2D6 substrateNon-substrate0.812
CYP450 3A4 substrateSubstrate0.5249
CYP450 1A2 substrateNon-inhibitor0.7993
CYP450 2C9 inhibitorNon-inhibitor0.7373
CYP450 2D6 inhibitorNon-inhibitor0.8832
CYP450 2C19 inhibitorNon-inhibitor0.7143
CYP450 3A4 inhibitorNon-inhibitor0.8596
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.978
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6302
BiodegradationReady biodegradable0.9593
Rat acute toxicity1.8100 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9939
hERG inhibition (predictor II)Non-inhibitor0.8552
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionintravenous
Injection, powder, lyophilized, for solutionintravenous; parenteral
Powder for solutionintravenous
Injection, powder, lyophilized, for solutionintravenous
Injection, solutionintravenous
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6207661 No1999-02-222019-02-22Us
US6900184 No2003-04-142023-04-14Us
US7129232 No2004-10-212024-10-21Us
US7915229 No2003-04-142023-04-14Us
US8133883 No2003-04-142023-04-14Us
US8476425 No2012-09-272032-09-27Us
US8685957 No2012-09-272032-09-27Us
US8906898 No2014-05-282034-05-28Us
US8968753 No2014-03-142034-03-14Us
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.59 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.82 m3·mol-1ChemAxon
Polarizability26.22 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis Reference

Georg Trickes, “Crystalline tazobactam, and its production and use.” U.S. Patent US5763603, issued March, 1988.

US5763603
General ReferencesNot Available
External Links
ATC CodesJ01CG02
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
DicoumarolTazobactam may increase the anticoagulant activities of Dicoumarol.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Tazobactam.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli
Pharmacological action
unknown
Actions
inhibitor
General Function:
Beta-lactamase activity
Specific Function:
Not Available
Gene Name:
bla
Uniprot ID:
P0AD63
Molecular Weight:
31223.635 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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:17016423 ]
Kind
Protein
Organism
Salmonella typhi
Pharmacological action
yes
Actions
inhibitor
General Function:
Beta-lactamase activity
Specific Function:
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.
Gene Name:
bla
Uniprot ID:
P62594
Molecular Weight:
31514.865 Da
References
  1. Yang Y, Rasmussen BA, Shlaes DM: Class A beta-lactamases--enzyme-inhibitor interactions and resistance. Pharmacol Ther. 1999 Aug;83(2):141-51. [PubMed:10511459 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on July 24, 2016 01:53