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 (0.5 g) + Piperacillin (4 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
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.25 g) + Piperacillin (2 g)Powder, for solutionIntravenousTeva2013-06-17Not applicableCanada
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.375 g) + Piperacillin (3 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 (1.5 g/60mL) + Piperacillin Sodium (12 g/60mL)Injection, powder, lyophilized, for solutionIntravenousFresenius Kabi2018-05-11Not applicableUs
Piperacillin and TazobactamTazobactam sodium (0.5 g/20mL) + Piperacillin Sodium (4 g/20mL)Injection, powder, for solutionIntravenousQilu Tianhe Pharmaceutical Co., Ltd.2018-08-10Not applicableUs
Piperacillin and TazobactamTazobactam sodium (0.5 g/20mL) + Piperacillin Sodium (4 g/20mL)Injection, powder, for solutionIntravenousAGILA SPECIALTIES PRIVATE LIMITED2014-08-162014-08-19Us
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][C@@]12CC(=O)N1[C@@H](C(O)=O)[C@](C)(CN1C=CN=N1)S2(=O)=O

Pharmacology

Indication

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

Associated Conditions
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
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Tazobactam is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Tazobactam is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Tazobactam is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Tazobactam is combined with Acenocoumarol.
AcetaminophenThe excretion of Tazobactam can be decreased when combined with Acetaminophen.
AcetazolamideThe excretion of Tazobactam can be decreased when combined with Acetazolamide.
Acetylsalicylic acidThe excretion of Tazobactam can be decreased when combined with Acetylsalicylic acid.
AcyclovirThe excretion of Tazobactam can be decreased when combined with Acyclovir.
Adefovir DipivoxilThe excretion of Tazobactam can be decreased when combined with Adefovir Dipivoxil.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Tazobactam.
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
HMDB0015544
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
J01CG02 — Tazobactam

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableInfection NOS1
1CompletedOtherHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentPeri-operative Prophylaxis / Proven or Suspected Gram-negative Bacterial Infection1
1RecruitingOtherDiabetes Mellitus (DM) / 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
2RecruitingTreatmentComplicated Intra-Abdominal Infections1
2RecruitingTreatmentComplicated Urinary Tract Infections / Pyelonephritis1
2RecruitingTreatmentOther Infectious Diseases1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
2TerminatedTreatmentOsteomyelitis1
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
3CompletedTreatmentHospital-acquired bacterial pneumonia1
3Not Yet RecruitingTreatmentHospital-acquired bacterial pneumonia / Pneumonia, Hospital-Acquired / Ventilator-associated Bacterial Pneumonia / Ventilator-Associated Pneumonia (VAP)1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentPneumonia, Bacterial1
3RecruitingTreatmentUrinary Tract Infections (UTIs)1
3TerminatedTreatmentVentilator-Associated Pneumonia (VAP)1
4CompletedNot AvailableInfections, Gram-Positive Bacterial1
4CompletedNot AvailableUrinary Tract Infections (UTIs)1
4CompletedHealth Services ResearchBacterial Infections1
4CompletedOtherCystic Fibrosis (CF) / Cystic Fibrosis Pulmonary Exacerbation / Pseudomonas Aeruginosa Infection1
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 RecruitingTreatmentBacteremia / Beta Lactam Resistant Bacterial Infection / Enterobacteriaceae Infections1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4RecruitingOtherChronic Obstructive Pulmonary Disease (COPD) / Pseudomonas Aeruginosa / Respiratory Tract Infections (RTI)1
4RecruitingOtherMinor burns / Pharmacokinetics1
4RecruitingPreventionFractures, Open / Post-Op Wound Infection1
4RecruitingTreatmentBloodstream Infections1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentAcute Renal Failure (ARF) / Shock, Septic1
4TerminatedTreatmentBloodstream Infections1
4TerminatedTreatmentCystic Fibrosis (CF)1
Not AvailableCompletedBasic ScienceBMI >30 kg/m21
Not AvailableCompletedTreatmentAppendicitis Acute1
Not AvailableCompletedTreatmentFebrile / Hematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1
Not AvailableNot Yet RecruitingNot AvailableBacterial Infections1
Not AvailableRecruitingNot AvailableCritical Illness / Infection NOS1
Not AvailableRecruitingTreatmentAppendicitis1
Not AvailableUnknown StatusPreventionHematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Apotex Inc.
  • Baxter International Inc.
  • Cardinal Health
  • Wyeth Pharmaceuticals
Dosage forms
FormRouteStrength
Injection, powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous; Parenteral
Powder, for solutionIntravenous
Injection, powder, lyophilized, for solutionIntravenous
Injection, solutionIntravenous
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6900184No2005-05-312023-04-14Us
US8133883No2012-03-132023-04-14Us
US7915229No2011-03-292023-04-14Us
US6207661No2001-03-272019-02-22Us
US7129232No2006-10-312024-10-21Us
US8685957No2014-04-012032-09-27Us
US8968753No2015-03-032034-03-14Us
US8476425No2013-07-022032-09-27Us
US8906898No2014-12-092034-05-28Us
US9320740No2016-04-262034-03-14Us
US9872906No2018-01-232034-03-14Us

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]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Wen S, Wang C, Duan Y, Huo X, Meng Q, Liu Z, Yang S, Zhu Y, Sun H, Ma X, Yang S, Liu K: OAT1 and OAT3 also mediate the drug-drug interaction between piperacillin and tazobactam. Int J Pharm. 2018 Feb 15;537(1-2):172-182. doi: 10.1016/j.ijpharm.2017.12.037. Epub 2017 Dec 23. [PubMed:29277663]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Wen S, Wang C, Duan Y, Huo X, Meng Q, Liu Z, Yang S, Zhu Y, Sun H, Ma X, Yang S, Liu K: OAT1 and OAT3 also mediate the drug-drug interaction between piperacillin and tazobactam. Int J Pharm. 2018 Feb 15;537(1-2):172-182. doi: 10.1016/j.ijpharm.2017.12.037. Epub 2017 Dec 23. [PubMed:29277663]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 08:52