Identification

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Name
Tazobactam
Accession Number
DB01606  (EXPT03012)
Type
Small Molecule
Groups
Approved
Description

Tazobactam is an antibiotic of the beta-lactamase inhibitor class that prevents the breakdown of other antibiotics by beta-lactamase enzyme producing organisms. It is combined with Piperacillin and Ceftolozane for the treatment of a variety of bacterial infections.

Piperacillin-tazobactam was initially approved by the FDA in 1994, and ceftolozane-tazobactam was approved by the FDA in 2014Label, providing wider antibacterial coverage for gram-negative infections. In June 2019, ceftolozane-tazobactam was approved by the FDA for treating hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia, which are significant causes of morbidity and mortality in hospitalized patients.14

Structure
Thumb
Synonyms
  • Tazobactam
  • Tazobactamum
External IDs
CL 298,741 / CL-298741 / 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 (0.5 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
Mylan-piperacillin and Tazobactam for InjectionTazobactam (0.25 g) + Piperacillin (2 g)Powder, for solutionIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.5 g) + Piperacillin (4 g)Powder, for solutionIntravenousTEVA Canada Limited2013-06-17Not applicableCanada
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.25 g) + Piperacillin (2 g)Powder, for solutionIntravenousTEVA Canada Limited2013-06-17Not applicableCanada
Piperacillin / Tazobactam Powder for InjectionTazobactam (0.375 g) + Piperacillin (3 g)Powder, for solutionIntravenousTEVA Canada Limited2013-06-17Not applicableCanada
Piperacillin and TazobactamTazobactam sodium (4.5 g/180mL) + Piperacillin sodium (36 g/180mL)Injection, powder, for solutionIntravenousFresenius Kabi USA, LLC2011-05-31Not applicableUs
Piperacillin and TazobactamTazobactam sodium (4.5 g/180mL) + Piperacillin sodium (36 g/180mL)Injection, powder, lyophilized, for solutionIntravenousApollo Pharmaceuticals Inc.2019-08-01Not applicableUs
Piperacillin and TazobactamTazobactam sodium (0.5 g/20mL) + Piperacillin sodium (4 g/20mL)Injection, powder, for solutionIntravenousSandoz2011-05-31Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Piperacillin, TazobactamTazobactam sodium (0.5 g/50mL) + Piperacillin sodium (4 g/50mL)Injection, powder, lyophilized, for solutionIntravenousX-GEN Pharmaceuticals, Inc.2017-02-142017-11-30Us
Piperacillin, TazobactamTazobactam sodium (0.375 g/20mL) + Piperacillin sodium (3 g/20mL)Injection, powder, lyophilized, for solutionIntravenousX-GEN Pharmaceuticals, Inc.2017-02-142017-11-30Us
Piperacillin, TazobactamTazobactam sodium (4.5 g/200mL) + Piperacillin sodium (36 g/200mL)Injection, powder, lyophilized, for solutionIntravenousX-GEN Pharmaceuticals, Inc.2017-02-142017-10-31Us
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

Tazobactam is used in combination with piperacillin or ceftolozane to broaden the spectrum of piperacillin antibacterial action, treating susceptible infections. As with any other antibiotic, tazobactam should only be used for infections that are either proven or strongly suspected to be susceptible to the tazobactam containing drug.

Tazobactam-piperacillin

When combined with piperacillin, it is used to treat a variety of infections, including those caused by aerobic and facultative gram-positive and gram-negative bacteria, in addition to gram-positive and gram-negative anaerobes. Some examples of infections treated with piperacillin-tazobactam include cellulitis, diabetic foot infections, appendicitis, and postpartum endometritis infections.11 Certain gram-negative bacilli infections with beta-lactamase producing organisms cannot be treated with piperacillin-tazobactam, due to a gene mutation conferring antibiotic resistance.1

Tazobactam-ceftolozane

Tazobactam-ceftolozane combined with metronidazole is used to treat complicated urinary tract infections (UTI) and complicated intra-abdominal infections, as well as ventilator-associated bacterial pneumonia and hospital-acquired bacterial pneumonia.Label. This combination increases efficacy against infections with gram-negative bacilli.2

Associated Conditions
Pharmacodynamics

Tazobactam inhibits the action of bacterial beta-lactamase producing organisms, which are normally resistant to beta-lactam antibiotics. This augments the effects of antibiotics which would otherwise not be effective in treating certain infections. These antibiotics contain a beta-lactam ring in their chemical structure, which is destroyed by beta-lactam resistant organisms.4 When combined with other antibiotics, a variety of infections, including serious and life-threatening infections may be treated.Label,11

Mechanism of action

Tazobactam broadens the spectrum of piperacillin11 and ceftolozaneLabel by making them effective against organisms that express beta-lactamase and would normally degrade them. This occurs through the irreversible inhibition of beta-lactamase enzymes. In addition, tazobactam may bind covalently to plasmid-mediated and chromosome-mediated beta-lactamase enzymes. Tazobactam is predominantly effective against the OHIO-1, SHV-1, and TEM groups of beta-lactamases, but may also inhibit other beta-lactamases.8,9,10

Tazobactam shows little antibacterial activity by itself, and for this reason, is generally not administered alone.Label

TargetActionsOrganism
ABeta-lactamase TEM
inhibitor
Salmonella typhi
ABeta-lactamase Ohio-1
inhibitor
Enterobacter cloacae
ABeta-lactamase SHV-1
inhibitor
Escherichia coli
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Tazobactam is coadministered with piperacillin or ceftolozane, pharmacokinetic information will be provided for these combinations.

Piperacillin-tazobactam

Peak plasma concentrations occur immediately after the completion of intravenous infusion. Following several doses of piperacillin-tazobactam infusions every 6 hours, peak concentrations were similar to those that were measured after the initial dose.11

Ceftolozane-piperacillin

AUC: 24.4-25 mcg•h/mL

Peak concentrations are reached on day 1 after the first dose and range from 18 to 18.4 mcg/mL.Label

Volume of distribution

18.2 L when given with piperacillin 11

13.5-18.2 L when given with ceftolozane Label

Piperacillin-tazobactam is widely distributed in body tissues and fluids. These may include but are not limited to the intestine, gallbladder, lung, female reproductive organs, and the bile. Meningeal distribution of piperacillin-tazobactam increases with inflammation, but is otherwise low.11

Protein binding

Tazobactam is bout 30% bound to plasma proteins.11

Metabolism

Tazobactam is mainly metabolized to M1, an inactive metabolite.11 Hydrolysis occurs on the beta-lactam ring to form M1 (the inactive metabolite).Label,5

Route of elimination

Tazobactam and its metabolite are mainly eliminated by the kidneys with about 80% of the administered dose eliminated as unchanged drug. The remaining drug is excreted as a single metabolite.11

Half life

Piperacillin-tazobactam

After a single dose in healthy volunteers, the plasma half-life of piperacillin and tazobactam was in the range of 0.7 to 1.2 hours.11

Ceftolozane-tazobactam

0.91-1.03 hours Label

Clearance

Because tazobactam is cleared by the kidneys and is a substrate of the transporters OAT1 and OAT3, inhibitors of these transporters should be avoided to ensure efficacy.11 Dosage adjustments of piperacillin-tazobactam and ceftolozane-tazobactam must be made for patients with impaired renal clearance.Label,11,12

The mean clearance rate of tazobactam was found to be 48.3-83.6 mL/min in patients admitted to the intensive care unit who were given renal replacement therapy and receiving intravenous piperacillin-tazobactam.6

The clearance of tazobactam is dependent on renal function, as determined by renal clearance.Label,7

Toxicity

Overdose

Post-marketing reports have been made of overdose cases with piperacillin/tazobactam. Nausea, vomiting, and diarrhea are frequent manifestations of an overdose. Neuromuscular excitability or seizures may also occur with high intravenous doses or renal failure. There is no specific antidote. Provide supportive measures in case of an overdose. Anticonvulsive agents may be indicated when neuromuscular excitability or seizures occur. If anaphylaxis occurs, traditional measures should be taken to manage hypersensitivity (for example, adrenaline, antihistamines, corticosteroids, and oxygen/airway maintenance).12 Similar measures should be taken after a ceftolozane-tazobactam overdose.Label Hemodialysis can be used to remove the drug from the circulation Label,11.

A note on nephrotoxicity

Cases of life-threatening nephrotoxicity have been seen in critically ill patients receiving piperacillin-tazobactam. Alternative therapy and/or renal monitoring should be considered in critically ill patients.13

Carcinogenesis/Mutagenesis

Tazobactam tested negative for genotoxic effects in the Ames assay, an after in vitro chromosomal aberration and point mutation assay in the Chinese hamster, an various other assays.Label

Use in pregnancy

Tazobactam has been found cross the placenta in rats. No data on human studies are available, however, rat studies have shown no teratogenetic effects at doses 6-14 times the equivalent maximum recommended human dose.11

Use in lactation

There are no data on the presence of tazobactam in human breastmilk. No data are currently available on the effects of tazobactam on the infant, or how it affects milk production. Use clinical judgement and consider the maternal need for the drug and the benefits of breastfeeding the infant before administration during lactation.11 Small concentrations of piperacillin-tazobactam have been found in the breastmilk and can lead to hypersensitivity in a breastfeeding infant. In some cases, breastfeeding may have to be discontinued temporarily.12

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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.
AbciximabThe risk or severity of bleeding can be increased when Tazobactam is combined with Abciximab.
AcenocoumarolThe risk or severity of bleeding can be increased when Tazobactam is combined with Acenocoumarol.
AcetazolamideThe excretion of Tazobactam can be decreased when combined with Acetazolamide.
Acetylsalicylic acidThe risk or severity of bleeding can be increased when Tazobactam is 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.
AllopurinolThe excretion of Allopurinol can be decreased when combined with Tazobactam.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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
  1. Gin A, Dilay L, Karlowsky JA, Walkty A, Rubinstein E, Zhanel GG: Piperacillin-tazobactam: a beta-lactam/beta-lactamase inhibitor combination. Expert Rev Anti Infect Ther. 2007 Jun;5(3):365-83. doi: 10.1586/14787210.5.3.365. [PubMed:17547502]
  2. Zhanel GG, Chung P, Adam H, Zelenitsky S, Denisuik A, Schweizer F, Lagace-Wiens PR, Rubinstein E, Gin AS, Walkty A, Hoban DJ, Lynch JP 3rd, Karlowsky JA: Ceftolozane/tazobactam: a novel cephalosporin/beta-lactamase inhibitor combination with activity against multidrug-resistant gram-negative bacilli. Drugs. 2014 Jan;74(1):31-51. doi: 10.1007/s40265-013-0168-2. [PubMed:24352909]
  3. Wise R, Logan M, Cooper M, Andrews JM: Pharmacokinetics and tissue penetration of tazobactam administered alone and with piperacillin. Antimicrob Agents Chemother. 1991 Jun;35(6):1081-4. doi: 10.1128/aac.35.6.1081. [PubMed:1656853]
  4. Williams JD: Beta-lactamases and beta-lactamase inhibitors. Int J Antimicrob Agents. 1999 Aug;12 Suppl 1:S3-7; discussion S26-7. [PubMed:10526867]
  5. Derendorf H, Dalla Costa T: Pharmacokinetics of piperacillin, tazobactam and its metabolite in renal impairment. Int J Clin Pharmacol Ther. 1996 Nov;34(11):482-8. [PubMed:8937930]
  6. Bauer SR, Salem C, Connor MJ Jr, Groszek J, Taylor ME, Wei P, Tolwani AJ, Fissell WH: Pharmacokinetics and pharmacodynamics of piperacillin-tazobactam in 42 patients treated with concomitant CRRT. Clin J Am Soc Nephrol. 2012 Mar;7(3):452-7. doi: 10.2215/CJN.10741011. Epub 2012 Jan 26. [PubMed:22282479]
  7. Wooley M, Miller B, Krishna G, Hershberger E, Chandorkar G: Impact of renal function on the pharmacokinetics and safety of ceftolozane-tazobactam. Antimicrob Agents Chemother. 2014;58(4):2249-55. doi: 10.1128/AAC.02151-13. Epub 2014 Feb 3. [PubMed:24492369]
  8. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [PubMed:9066111]
  9. Schechter LM, Creely DP, Garner CD, Shortridge D, Nguyen H, Chen L, Hanson BM, Sodergren E, Weinstock GM, Dunne WM Jr, van Belkum A, Leopold SR: Extensive Gene Amplification as a Mechanism for Piperacillin-Tazobactam Resistance in Escherichia coli. MBio. 2018 Apr 24;9(2). pii: mBio.00583-18. doi: 10.1128/mBio.00583-18. [PubMed:29691340]
  10. Pagan-Rodriguez D, Zhou X, Simmons R, Bethel CR, Hujer AM, Helfand MS, Jin Z, Guo B, Anderson VE, Ng LM, Bonomo RA: Tazobactam inactivation of SHV-1 and the inhibitor-resistant Ser130 -->Gly SHV-1 beta-lactamase: insights into the mechanism of inhibition. J Biol Chem. 2004 May 7;279(19):19494-501. doi: 10.1074/jbc.M311669200. Epub 2004 Feb 2. [PubMed:14757767]
  11. Zosyn (Piperacillin and Tazobactam) FDA Label [Link]
  12. Medsafe NZ: Tazocin [Link]
  13. Pfizer medical information [Link]
  14. FDA approval information, Zerbaxa [Link]
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
FDA label
Download (707 KB)
MSDS
Download (25.8 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableImpaired Renal Function1
1CompletedNot AvailableInfection NOS1
1CompletedOtherDiabetes Mellitus (DM) / Healthy Volunteers / Wound Infections1
1CompletedOtherHealthy Volunteers2
1CompletedOtherSepsis1
1CompletedTreatmentCritically-ill Patients / Pneumonia1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentPeri-operative Prophylaxis / Proven or Suspected Gram-negative Bacterial Infection1
1RecruitingTreatmentInfection NOS1
1, 2Active Not RecruitingTreatmentOtitis Media (OM) / Otorrhoea1
1, 2Not Yet RecruitingBasic SciencePharmacokinetics1
2CompletedTreatmentComplicated Intra-Abdominal Infections1
2CompletedTreatmentCritical Illness / Hospital Acquired Infections / Pneumonia / Pyrexia / Systemic Inflammatory Response Syndrome (SIRS)1
2Not Yet RecruitingPreventionAllogeneic Hematopoietic Stem Cell Transplantation Recipient / Graft-versus-host Disease Prevention1
2RecruitingTreatmentComplicated Intra-Abdominal Infections1
2RecruitingTreatmentComplicated Urinary Tract Infections / Pyelonephritis1
2RecruitingTreatmentIntestinal Microbiome / Neutropenia, Febrile1
2RecruitingTreatmentOther Infectious Diseases1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
2TerminatedTreatmentOsteomyelitis1
2, 3CompletedTreatmentAcute Pyelonephritis / Urinary Tract Infection Complicated / Urinary Tract Infection Symptomatic1
2, 3CompletedTreatmentComplicated Intra Abdominal Infections1
2, 3RecruitingTreatmentAbdominal Infection1
2, 3Unknown StatusTreatmentTracheobronchitis1
3Active Not RecruitingTreatmentSevere Septic Syndrome (Severe Sepsis and Septic Shock) Diagnosed and Treated by Mobile Intensive Care Unit1
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
3CompletedTreatmentAbscess, Intra-Abdominal1
3CompletedTreatmentAbscesses / Diabetic Foot / Ulcers / Wound Infections1
3CompletedTreatmentAcute Calculous Cholecystitis1
3CompletedTreatmentAcute Pyelonephritis / Urinary Tract Infection Complicated1
3CompletedTreatmentChronic Lung Diseases / Healthcare-Associated Pneumonia / Hospital-acquired bacterial pneumonia / Ventilator-Associated Pneumonia (VAP)1
3CompletedTreatmentComplicated Intra-Abdominal Infections1
3CompletedTreatmentComplicated Intra-Abdominal Infections / Intra-Abdominal Infections1
3CompletedTreatmentComplicated Urinary Tract Infections / Pyelonephritis / Uncomplicated Pyelonephritis / Urinary Tract Infections (UTIs)1
3CompletedTreatmentFoot Infections in Diabetic Patients1
3CompletedTreatmentInfection; Diabetic Foot1
3CompletedTreatmentNeoplasms, Hematologic1
3CompletedTreatmentPneumonia1
3CompletedTreatmentPneumonia, Bacterial1
3CompletedTreatmentPseudomonas Aeruginosa Infection1
3Not Yet RecruitingTreatmentSurgical Site Infections1
3RecruitingTreatmentComplicated Intra-Abdominal Infections1
3RecruitingTreatmentEnterobacteriaceae Infections1
3RecruitingTreatmentMalignant Neoplasm of Pancreas / Pancreatic Diseases1
3RecruitingTreatmentShock, Septic1
3RecruitingTreatmentUrinary Tract Infections (UTIs)1
3RecruitingTreatmentVentilator-Associated Pneumonia (VAP)1
3TerminatedTreatmentVentilator-Associated Pneumonia (VAP)1
3WithdrawnTreatmentHospital-acquired bacterial pneumonia / Pneumonia, Hospital-Acquired / Ventilator-associated Bacterial Pneumonia / Ventilator-Associated Pneumonia (VAP)1
4Active Not RecruitingTreatmentCystic Fibrosis (CF)1
4CompletedNot AvailableHaematological Malignancies / Leukemias / Malignant Lymphomas / Myelodysplasia / Plasma Cell Myeloma / Transplantation, Stem Cell1
4CompletedNot AvailableInfection Due to Escherichia Coli / Infections, Gram-Positive Bacterial / Klebsiella Infections1
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
4CompletedTreatmentInfection NOS / Pneumonia1
4Enrolling by InvitationTreatmentEarly Phase of Severe Sepsis and Septic Shock1
4Enrolling by InvitationTreatmentPatients Who Received Imipenem or Meropenem or Piperacillin/Tazobactam or Sulbactam in ICU1
4Not Yet RecruitingTreatmentAntibiotic Resistance, Bacterial / Carbapenem / Clinical Trial / Enterobacteriaceae Infections / Infection Due to ESBL Bacteria / Infection Due to Escherichia Coli / Klebsiella Pneumoniae Infection / Urinary Tract Infections (UTIs)1
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
4RecruitingTreatmentAppendicitis1
4RecruitingTreatmentBacteremia / Beta Lactam Resistant Bacterial Infection / Enterobacteriaceae Infections1
4RecruitingTreatmentBloodstream Infections1
4RecruitingTreatmentCommunity Acquired Pneumonia (CAP)1
4RecruitingTreatmentPerforated Appendicitis / Postoperative Infections1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedTreatmentAcute Renal Failure (ARF) / Shock, Septic1
4TerminatedTreatmentBloodstream Infections1
4TerminatedTreatmentCystic Fibrosis (CF)1
4TerminatedTreatmentMinor burns1
Not AvailableActive Not RecruitingNot AvailablePseudomonas Aeruginosa / Pseudomonas Infections1
Not AvailableActive Not RecruitingTreatmentAppendicitis / Complicated Appendicitis / Perforated Appendicitis / Ruptured Appendicitis1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedBasic ScienceBMI >30 kg/m21
Not AvailableCompletedPreventionNeonatal Sepsis1
Not AvailableCompletedTreatmentAppendicitis Acute1
Not AvailableCompletedTreatmentChronic Bronchitis / Cystic Fibrosis (CF)1
Not AvailableCompletedTreatmentFebrile / Hematopoietic Stem Cell Transplantation (HSCT) / Neutropenias1
Not AvailableCompletedTreatmentShock, Septic1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Injury (AKI) / Haemodiafiltration / Sepsis1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1
Not AvailableNot Yet RecruitingNot AvailableResuscitation Patients With Sepsis1
Not AvailableNot Yet RecruitingTreatmentSepsis / Shock, Septic / Systemic Inflammatory Response Syndrome (SIRS)1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiety / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Bradycardia / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Cardiac Dysrhythmia / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Chronic Kidney Disease (CKD) / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Endocarditis / Epilepsies / Fibrinolytic Bleeding / Flu caused by Influenza / Gastroparesis / Gram-negative Infection / Gynaecological infection / Headaches / Heart Failure / Heavy Menstrual Bleeding / Hemophilia / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperaldosteronism / Hyperlipidemias / Hypokalaemia / Infantile Hemangiomas / Infection caused by staphylococci / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Methicillin Resistant Staphylococcus Aureus (MRSA) / Migraine / Muscle Spasms / Nausea / Neuromuscular Blockade / Neutropenias / Oedema / Opioid Addiction / Pain NOS / Plague / Pneumonia / Prophylaxis / Psittacosis / Pulmonary Arterial Hypertension (PAH) / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Sleeplessness / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingNot AvailableAntibiotic Selection Pressure1
Not AvailableRecruitingNot AvailableBacterial Infections1
Not AvailableRecruitingNot AvailableCritical Illness1
Not AvailableRecruitingNot AvailableCritical Illness / Infection NOS1
Not AvailableRecruitingNot AvailableDrug Effect1
Not AvailableRecruitingNot AvailableEarly Onset Neonatal Sepsis1
Not AvailableRecruitingNot AvailableGeneral Surgery1
Not AvailableRecruitingPreventionAntibiotic Prophylaxis / Postoperative Infections1
Not AvailableRecruitingTreatmentAppendicitis1
Not AvailableRecruitingTreatmentSepsis1
Not AvailableSuspendedBasic ScienceCystic Fibrosis (CF)1
Not AvailableTerminatedTreatmentAppendicitis1
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
PowderNot applicable
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
US10125149No2018-11-132035-08-14Us
US9724353No2017-08-082032-09-07Us
US10028963No2018-07-242032-09-07Us
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)140-147https://www.caymanchem.com/msdss/17185m.pdf
boiling point (°C)77https://www.chemicalbook.com/ChemicalProductProperty_US_CB3181854.aspx
water solubility50 mg/mLhttps://www.chemicalbook.com/ChemicalProductProperty_US_CB3181854.aspx
pKa2.1Not 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
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]
  2. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [PubMed:9066111]
  3. Schechter LM, Creely DP, Garner CD, Shortridge D, Nguyen H, Chen L, Hanson BM, Sodergren E, Weinstock GM, Dunne WM Jr, van Belkum A, Leopold SR: Extensive Gene Amplification as a Mechanism for Piperacillin-Tazobactam Resistance in Escherichia coli. MBio. 2018 Apr 24;9(2). pii: mBio.00583-18. doi: 10.1128/mBio.00583-18. [PubMed:29691340]
Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
Beta-lactamase activity
Gene Name
Not Available
Uniprot ID
P18251
Uniprot Name
Beta-lactamase Ohio-1
Molecular Weight
31353.795 Da
References
  1. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [PubMed:9066111]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Yes
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. Pagan-Rodriguez D, Zhou X, Simmons R, Bethel CR, Hujer AM, Helfand MS, Jin Z, Guo B, Anderson VE, Ng LM, Bonomo RA: Tazobactam inactivation of SHV-1 and the inhibitor-resistant Ser130 -->Gly SHV-1 beta-lactamase: insights into the mechanism of inhibition. J Biol Chem. 2004 May 7;279(19):19494-501. doi: 10.1074/jbc.M311669200. Epub 2004 Feb 2. [PubMed:14757767]
  2. Bonomo RA, Rudin SA, Shlaes DM: Tazobactam is a potent inactivator of selected inhibitor-resistant class A beta-lactamases. FEMS Microbiol Lett. 1997 Mar 1;148(1):59-62. doi: 10.1111/j.1574-6968.1997.tb10267.x. [PubMed:9066111]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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]
  2. FDA label, Zerbaxa [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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]
  2. Clinical pharmacology and biopharmaceutics review [Link]
  3. FDA label, Zerbaxa [Link]

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 21:50