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
Thumb
Synonyms
  • CL-298741
  • Tazobactam
  • YTR-830H
Product Ingredients
IngredientUNIICASInChI Key
Tazobactam sodiumUXA545ABTT89785-84-2RFMIKMMOLPNEDG-QVUDESDKSA-M
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Jamp-pip/tazTazobactam (0.5 g) + Piperacillin (4 g)Powder, for solutionIntravenousJamp Pharma Corporation2014-03-12Not applicableCanada
Mylan-piperacillin and Tazobactam for InjectionTazobactam (0.25 g) + Piperacillin (2 g)Powder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-piperacillin and Tazobactam for InjectionTazobactam (0.375 g) + Piperacillin (3 g)Powder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-piperacillin and Tazobactam for InjectionTazobactam (0.5 g) + Piperacillin (4 g)Powder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.375 g) + Piperacillin (3 g)Powder, for solutionIntravenousTeva2013-06-17Not applicableCanada
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.25 g) + Piperacillin (2 g)Powder, for solutionIntravenousTeva2013-06-17Not applicableCanada
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.5 g) + Piperacillin (4 g)Powder, for solutionIntravenousTeva2013-06-17Not applicableCanada
Piperacillin and TazobactamTazobactam sodium (.5 g/20mL) + Piperacillin Sodium (4 g/20mL)Injection, powder, for solutionIntravenousMylan Institutional2014-08-16Not applicableUs
Piperacillin and TazobactamTazobactam sodium (.5 g/20mL) + Piperacillin Sodium (4 g/20mL)Injection, powder, lyophilized, for solutionIntravenous; ParenteralHospira, Inc.2010-10-21Not applicableUs
Piperacillin and TazobactamTazobactam sodium (.375 g/15mL) + Piperacillin Sodium (3 g/15mL)Injection, powder, for solutionIntravenousWG Critical Care, LLC2009-10-13Not applicableUs
Categories
UNII
SE10G96M8W
CAS number
89786-04-9
Weight
Average: 300.291
Monoisotopic: 300.052840204
Chemical Formula
C10H12N4O5S
InChI Key
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][[email protected]@]12CC(=O)N1[[email protected]@H](C(O)=O)[[email protected]](C)(CN1C=CN=N1)S2(=O)=O

Pharmacology

Indication

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

Structured Indications
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.

TargetActionsOrganism
UBeta-lactamase SHV-1
inhibitor
Escherichia coli
ABeta-lactamase TEM
inhibitor
Salmonella typhi
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolTazobactam may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Tazobactam.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Tazobactam.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Tazobactam.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Tazobactam.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Tazobactam.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Tazobactam.Approved, Investigational
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Tazobactam.Investigational
BekanamycinThe serum concentration of Bekanamycin can be decreased when it is combined with Tazobactam.Experimental
ChlortetracyclineThe therapeutic efficacy of Tazobactam can be decreased when used in combination with Chlortetracycline.Approved, Investigational, Vet Approved
ClorindioneTazobactam may increase the anticoagulant activities of Clorindione.Experimental
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Tazobactam.Approved
DemeclocyclineThe therapeutic efficacy of Tazobactam can be decreased when used in combination with Demeclocycline.Approved
DibekacinThe serum concentration of Dibekacin can be decreased when it is combined with Tazobactam.Experimental
DicoumarolTazobactam may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Tazobactam.Investigational, Vet Approved
DiphenadioneTazobactam may increase the anticoagulant activities of Diphenadione.Experimental
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Tazobactam.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Tazobactam can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Tazobactam.Approved
Ethyl biscoumacetateTazobactam may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneTazobactam may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Tazobactam.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Tazobactam.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Tazobactam.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Tazobactam.Experimental
GPX-150The serum concentration of GPX-150 can be decreased when it is combined with Tazobactam.Investigational
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Tazobactam.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Tazobactam.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Tazobactam.Investigational
IsepamicinThe serum concentration of Isepamicin can be decreased when it is combined with Tazobactam.Experimental
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Tazobactam.Approved, Investigational, Vet Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Tazobactam.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Tazobactam.Approved
MicronomicinThe serum concentration of Micronomicin can be decreased when it is combined with Tazobactam.Experimental
MinocyclineThe therapeutic efficacy of Tazobactam can be decreased when used in combination with Minocycline.Approved, Investigational
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Tazobactam resulting in a loss in efficacy.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Tazobactam.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Tazobactam.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Tazobactam.Approved, Investigational
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Tazobactam.Approved, Investigational
PhenindioneTazobactam may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonTazobactam may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Tazobactam.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Tazobactam.Investigational
PlazomicinThe serum concentration of Plazomicin can be decreased when it is combined with Tazobactam.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Tazobactam.Approved, Investigational, Withdrawn
ProbenecidThe serum concentration of Tazobactam can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Tazobactam.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Tazobactam.Approved, Investigational
SabarubicinThe serum concentration of Sabarubicin can be decreased when it is combined with Tazobactam.Investigational
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Tazobactam.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Tazobactam.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Tazobactam.Approved, Investigational, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Tazobactam.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Tazobactam.Approved
TioclomarolTazobactam may increase the anticoagulant activities of Tioclomarol.Experimental
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Tazobactam.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Tazobactam.Approved
WarfarinTazobactam may increase the anticoagulant activities of Warfarin.Approved
Zoptarelin doxorubicinThe serum concentration of Zoptarelin doxorubicin can be decreased when it is combined with Tazobactam.Investigational
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Tazobactam.Experimental
Food Interactions
Not Available

References

Synthesis Reference

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

US5763603
General References
Not Available
External Links
Human Metabolome Database
HMDB15544
KEGG Drug
D00660
KEGG Compound
C07771
PubChem Compound
123630
PubChem Substance
46508088
ChemSpider
110216
BindingDB
50053173
ChEBI
9421
ChEMBL
CHEMBL404
Therapeutic Targets Database
DAP000926
PharmGKB
PA164764504
Wikipedia
Tazobactam
ATC Codes
J01CR50 — Combinations of penicillinsJ01CG02 — Tazobactam

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableInfection NOS1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentPeri-operative Prophylaxis / Proven or Suspected Gram-negative Bacterial Infection1
1RecruitingOtherDiabetes / Healthy Volunteers / Wound Infections1
1RecruitingTreatmentInfection NOS1
1, 2Not Yet RecruitingBasic SciencePharmacokinetics1
2CompletedTreatmentComplicated Intra-Abdominal Infections1
2CompletedTreatmentCritical Illness / Hospital Acquired Infections / Pneumonia / Pyrexia / Systemic Inflammatory Response Syndrome (SIRS)1
2Not Yet RecruitingTreatmentComplicated Intra-Abdominal Infections1
2Not Yet RecruitingTreatmentComplicated Urinary Tract Infections / Pyelonephritis1
2RecruitingTreatmentOsteomyelitis1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
3CompletedSupportive CareBone Marrow Suppression / Fever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Unspecified Adult Solid Tumor, Protocol Specific / Unspecified Childhood Solid Tumor, Protocol Specific1
3CompletedTreatmentInfection; Diabetic Foot1
3CompletedTreatmentNeoplasms, Hematologic1
3CompletedTreatmentPneumonia1
3Not Yet RecruitingTreatmentHospital-acquired bacterial pneumonia / Pneumonia, Hospital-Acquired / Ventilator-associated Bacterial Pneumonia / Ventilator-Associated Pneumonia (VAP)1
3RecruitingNot AvailablePneumonia, Bacterial1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentHospital-acquired bacterial pneumonia1
3TerminatedTreatmentVentilator-Associated Pneumonia (VAP)1
4CompletedNot AvailableCystic Fibrosis (CF) / Cystic Fibrosis Pulmonary Exacerbation / Pseudomonas Aeruginosa Infection1
4CompletedNot AvailableInfections, Gram-Positive Bacterial1
4CompletedNot AvailableUrinary Tract Infections (UTIs)1
4CompletedHealth Services ResearchBacterial Infections1
4CompletedPreventionBacterial Infections1
4CompletedTreatmentBacterial Infections1
4CompletedTreatmentBody Clearance / Diffusive and Convective Clearance / Piperacillin Tazocilline Concentrations (Cmin)1
4CompletedTreatmentDiabetes Mellitus (DM) / Diabetic Foot1
4Enrolling by InvitationTreatmentEarly Phase of Severe Sepsis and Septic Shock1
4Not Yet RecruitingOtherChronic Obstructive Pulmonary Disease (COPD) / Pseudomonas Aeruginosa / Respiratory Tract Infections (RTI)1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4RecruitingOtherMinor burns / Pharmacokinetics1
4RecruitingTreatmentBloodstream Infections1
4SuspendedTreatmentBloodstream Infections1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentAcute Renal Failure (ARF) / Shock, Septic1
4TerminatedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedBasic ScienceBMI >30 kg/m21
Not AvailableCompletedTreatmentAcute Appendicitis1
Not AvailableCompletedTreatmentFebrile / Hematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1
Not AvailableRecruitingNot AvailableCritical Illness / Infection NOS1
Not AvailableRecruitingTreatmentAppendicitis1
Not AvailableUnknown StatusPreventionHematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous; Parenteral
Powder, for solutionIntravenous
Injection, solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6900184No2003-04-142023-04-14Us
US8133883No2003-04-142023-04-14Us
US7915229No2003-04-142023-04-14Us
US6207661No1999-02-222019-02-22Us
US7129232No2004-10-212024-10-21Us
US8685957No2012-09-272032-09-27Us
US8968753No2014-03-142034-03-14Us
US8476425No2012-09-272032-09-27Us
US8906898No2014-05-282034-05-28Us
US9320740No2014-03-142034-03-14Us

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Penams / Triazoles / Thiazolidines / Tertiary carboxylic acid amides / Sulfones / Heteroaromatic compounds / Azetidines / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
Alpha-amino acid or derivatives / Penam / Azole / Beta-lactam / Sulfone / Heteroaromatic compound / Tertiary carboxylic acid amide / Thiazolidine / 1,2,3-triazole / Azetidine
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
triazoles, penicillanic acids (CHEBI:9421)

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
Uniprot Name
Beta-lactamase SHV-1
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 cephalos...
Gene Name
bla
Uniprot ID
P62594
Uniprot Name
Beta-lactamase TEM
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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:02