TAZOBACTAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12N4O5S
Molecular Weight	300.2926
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]1(Cn2ccnn2)[C@]([H])(C(=O)O)N3C(=O)C[C@@]3([H])S1(=O)=O

InChI

InChIKey=LPQZKKCYTLCDGQ-WEDXCCLWSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf | http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206829s003lbl.pdf

Tazobactam is a beta-lactamase inhibitor, which was approved by FDA for the treatment of wide range of bacterial infections either in combination with piperacillin (Zosyn) or with ceftolozane (Zerbaxa).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial beta-lactamase TEM 10 Target ID: CHEMBL2364670 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206829s003lbl.pdf	Inhibitor 7728		0.01 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Intra-abdominal infections 46 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8043	ZOSYN Approved Use ZOSYN is a combination product consisting of a penicillin-class antibacterial, piperacillin, and a beta-lactamase inhibitor, tazobactam, indicated for the treatment of patients with intra-abdominal infections; skin and skin structure infections; female pelvic infections; community-acquired pneumonia; nosocomial pneumonia. Launch Date 7.5124802E11
Skin and skin structure infections 77 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8043	ZOSYN Approved Use ZOSYN is a combination product consisting of a penicillin-class antibacterial, piperacillin, and a beta-lactamase inhibitor, tazobactam, indicated for the treatment of patients with intra-abdominal infections; skin and skin structure infections; female pelvic infections; community-acquired pneumonia; nosocomial pneumonia. Launch Date 7.5116157E11
Female pelvic infections 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8043	ZOSYN Approved Use ZOSYN is a combination product consisting of a penicillin-class antibacterial, piperacillin, and a beta-lactamase inhibitor, tazobactam, indicated for the treatment of patients with intra-abdominal infections; skin and skin structure infections; female pelvic infections; community-acquired pneumonia; nosocomial pneumonia. Launch Date 7.5116157E11
Pneumonia 90 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8043	ZOSYN Approved Use ZOSYN is a combination product consisting of a penicillin-class antibacterial, piperacillin, and a beta-lactamase inhibitor, tazobactam, indicated for the treatment of patients with intra-abdominal infections; skin and skin structure infections; female pelvic infections; community-acquired pneumonia; nosocomial pneumonia. Launch Date 7.5116157E11
Complicated urinary tract infections 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206829s003lbl.pdf	Curative	Approved 8043	ZERBAXA Approved Use ZERBAXA (ceftolozane and tazobactam) is a combination product consisting of a cephalosporin-class antibacterial drug and a beta-lactamase inhibitor indicated for the treatment of complicated Intra-abdominal Infections, used in combination with metronidazole and complicated Urinary Tract Infections, including Pyelonephritis. Launch Date 1.4189472E12

C_max

Value	Dose	Co-administered	Analyte	Population
18.4 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
18 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg 3 times / day steady-state, intravenous dose: 500 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
6.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1656853/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TAZOBACTAM unknown	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
15 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	250 mg 4 times / day multiple, intravenous dose: 250 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
24 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	375 mg 4 times / day multiple, intravenous dose: 375 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
34 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	500 mg 4 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
24.4 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
25 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg 3 times / day steady-state, intravenous dose: 500 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
42.4 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1656853/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
18 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1656853/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TAZOBACTAM unknown	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
16 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	250 mg 4 times / day multiple, intravenous dose: 250 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
25 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	375 mg 4 times / day multiple, intravenous dose: 375 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
39.8 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	500 mg 4 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.91 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.03 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg 3 times / day steady-state, intravenous dose: 500 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.13 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1656853/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.94 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1656853/	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered:		TAZOBACTAM unknown	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.77 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	250 mg 4 times / day multiple, intravenous dose: 250 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
0.68 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	375 mg 4 times / day multiple, intravenous dose: 375 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
0.82 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	500 mg 4 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	500 mg 3 times / day steady-state, intravenous dose: 500 mg route of administration: Intravenous experiment type: STEADY-STATE co-administered: CEFTOLOZANE	CEFTOLOZANE	TAZOBACTAM plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	250 mg 4 times / day multiple, intravenous dose: 250 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	375 mg 4 times / day multiple, intravenous dose: 375 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/050684s88s89s90_050750s37s38s39lbl.pdf	500 mg 4 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: PIPERACILLIN	PIPERACILLIN	TAZOBACTAM plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
1 g 3 times / day multiple, intravenous Dose: 1 g, 3 times / day Route: intravenous Route: multiple Dose: 1 g, 3 times / day Co-administed with:: ceftolozane(2 g; 3/day) Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/	healthy, 36 n = 8 Health Status: healthy Age Group: 36 Sex: M Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/	Disc. AE: Vomiting... Other AEs: Nausea, Infusion site inflammation... AEs leading to discontinuation/dose reduction: Vomiting (12.5%) Other AEs: Nausea (12.5%) Infusion site inflammation (12.5%) Infusion site irritation (25%) Pain in extremity (12.5%) Flushing (12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/
0.5 g 3 times / day multiple, intravenous Recommended Dose: 0.5 g, 3 times / day Route: intravenous Route: multiple Dose: 0.5 g, 3 times / day Co-administed with:: ceftolozane(1 g; 3/day) Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/	healthy, 39 n = 4 Health Status: healthy Age Group: 39 Sex: M Population Size: 4 Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/	Other AEs: Infusion site irritation, Sensation of heaviness... Other AEs: Infusion site irritation (25%) Sensation of heaviness (25%) Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/
0.5 g 3 times / day multiple, intravenous Recommended Dose: 0.5 g, 3 times / day Route: intravenous Route: multiple Dose: 0.5 g, 3 times / day Co-administed with:: ceftolozane(1 g; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	unhealthy, adult n = 1015 Health Status: unhealthy Condition: Infections Age Group: adult Population Size: 1015 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	Disc. AE: Renal impairment... AEs leading to discontinuation/dose reduction: Renal impairment (0.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
0.5 g 3 times / day multiple, intravenous Recommended Dose: 0.5 g, 3 times / day Route: intravenous Route: multiple Dose: 0.5 g, 3 times / day Co-administed with:: ceftolozane(1 g; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	unhealthy, adult n = 482 Health Status: unhealthy Condition: Complicated Intra-abdominal Infections Age Group: adult Population Size: 482 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	Other AEs: Nausea, Headache... Other AEs: Nausea (7.9%) Headache (2.5%) Diarrhea (6.2%) Pyrexia (5.6%) Constipation (1.9%) Insomnia (3.5%) Vomiting (3.3%) Hypokalemia (3.3%) ALT increased (1.5%) AST increased (1%) Anemia (1.5%) Thrombocytosis (1.9%) Abdominal pain (1.2%) Anxiety (1.9%) Dizziness (0.8%) Hypotension (1.7%) Atrial fibrillation (1.2%) Rash (1.7%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf
0.5 g 3 times / day multiple, intravenous Recommended Dose: 0.5 g, 3 times / day Route: intravenous Route: multiple Dose: 0.5 g, 3 times / day Co-administed with:: ceftolozane(1 g; 3/day) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	unhealthy, adult n = 533 Health Status: unhealthy Condition: Complicated Urinary Tract Infections, Including Pyelonephritis Age Group: adult Population Size: 533 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	Other AEs: Anxiety, Dizziness... Other AEs: Anxiety (0.2%) Dizziness (1.1%) Hypotension (0.4%) Nausea (2.8%) Headache (5.8%) Diarrhea (1.9%) Pyrexia (1.7%) Constipation (3.9%) Insomnia (1.3%) Vomiting (1.1%) Hypokalemia (0.8%) ALT increased (1.7%) AST increased (1.7%) Anemia (0.4%) Thrombocytosis (0.4%) Abdominal pain (0.8%) Atrial fibrillation (0.2%) Rash (0.9%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
supressor 19 inhibitor 1467	inhibitor 1604	inhibitor 1702

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 554 OAT3 588 CYP1A2 1383 CYP2B6 717 CYP2C8 818 CYP2C19 1325 P-gp 1330 OATP1B1 733 OATP1B3 657 OCT1 480 OCT2 594 BCRP 643 BSEP 376	OAT1 294 OAT3 305 P-gp 1400

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 713	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
BCRP 713	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
BSEP 377	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
BSEP 377	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2B6 884	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2B6 884	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C19 1392	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C8 865	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C8 865	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C9 1648	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2D6 1738	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OAT3 590	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OATP1B1 748	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
OATP1B1 748	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OATP1B3 666	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OCT2 595	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
P-gp 1514	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
P-gp 1514	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP1A2 1532	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no		unlikely (co-administration study) Comment: In general, the results of these in vitro trials did not suggest a potential for drug interactions Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf
OATP1B3 666	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	weak
OCT1 495	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	weak
CYP3A4 1772	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	weak		yes (co-administration study) Comment: Tazobactam showed some inhibition of CYP3A4 at concentrations well above the expected clinical concentration of 22 µg/mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf
CYP1A2 1532	supressor 140 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes
CYP1A2 1532	supressor 140 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
CYP2B6 884	supressor 140 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
CYP3A4 1772	supressor 140 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes
CYP3A4 1772	supressor 140 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
OAT1 558	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
OAT1 558	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes		yes (co-administration study) Comment: IC50 = 117.7 ug/mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf
OAT3 590	inhibitor 3045 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes		yes (co-administration study) Comment: IC50 = 146.7 ug/mL Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf

Drug as victim

Target	Modality	Activity
P-gp 1400	substrate 3113 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
OAT1 294	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/29277663/	yes
OAT3 305	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/29277663/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9421	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9421
ChemicalBook	CB7473784	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7473784
MolPort	MolPort-002-500-123	https://www.molport.com/shop/molecule-link/MolPort-002-500-123
ZINC	ZINC000003787060	http://zinc15.docking.org/substances/ZINC000003787060
eMolecules	2724829	https://www.emolecules.com/cgi-bin/more?vid=2724829
eMolecules	29706580	https://www.emolecules.com/cgi-bin/more?vid=29706580
eMolecules	36552982	https://www.emolecules.com/cgi-bin/more?vid=36552982

PubMed

Title	Date	PubMed
[Multicentre clinical trial on efficacy and safety of domestic piperacillin/tazobactam for treatment of acute bacterial infections].	2001 Jan 10	11798851
Faecal concentrations of piperacillin and tazobactam in elderly patients.	2001 Jul	11418534
Inactivation of CMY-2 beta-lactamase by tazobactam: initial mass spectroscopic characterization.	2001 Jun 11	11410275
Penicillins and beta-lactamase inhibitor combinations.	2001 Jun 15	11417732
De-escalation antimicrobial chemotherapy in critically III patients: pros and cons.	2001 Nov	11936369
CAPD-associated peritonitis caused by Alcaligenes xylosoxidans sp. xylosoxidans.	2001 Nov-Dec	11799270
Piperacillin/Tazobactam versus cefotaxime plus metronidazole for treatment of children with intra-abdominal infections requiring surgery.	2001 Sep	11714046
[Identification and susceptibility to antimicrobial agents of strictly anaerobic bacteria isolated from hospitalized patients].	2002	12632658
Probing substrate binding to metallo-beta-lactamase L1 from Stenotrophomonas maltophilia by using site-directed mutagenesis.	2002	11876827
[Candida parapsilosis endocarditis after prolonged antibiotic therapy].	2002 Apr	14606382
[A multicenter clinical trial of piperacillin/tazobactam in burn infection].	2002 Apr	12515649
Gateways to Clinical Trials.	2002 Apr	12087878
[Initial empirical antimicrobial therapy with piperacillin/tazobactam in intra-abdominal infections due to perforation of the large intestine and rectum and in postoperative complications after resection of the large intestine and rectum].	2002 Dec	12666475
Postoperative infection with group A beta-hemolytic Streptococcus after blepharoplasty.	2002 Dec	12470763
Biochemical analysis of the ceftazidime-hydrolysing extended-spectrum beta-lactamase CTX-M-15 and of its structurally related beta-lactamase CTX-M-3.	2002 Dec	12461028
Localised necrosis of scrotum (Fournier's gangrene) in a spinal cord injury patient - a case report.	2002 Dec 5	12466026
[Study on water of crystallization in tazobactam].	2002 Feb	12579963
[In vitro interaction of tazobactam/piperacillin combined with aminoglycosides against Pseudomonas aeruginosa, Klebsiella pneumoniae, Escherichia coli AND Staphylococcus aureus].	2002 Feb	11977921
Penetration of piperacillin/tazobactam (4 g/500 mg) into synovial tissue.	2002 Feb	11892900
Antibacterial activities of beta-lactamase inhibitors associated with morphological changes of cell wall in Helicobacter pylori.	2002 Feb	11886472
[Susceptibility of Pseudomonas aeruginosa to antibiotics isolated from patients of intensive care units in France in 1998. Resistant phenotypes to beta-lactams].	2002 Feb	11873623
Piperacillin 2 g/tazobactam 0.5 g is as effective as imipenem 0.5 g/cilastatin 0.5 g for the treatment of acute uncomplicated pyelonephritis and complicated urinary tract infections.	2002 Feb	11850161
Clinafloxacin versus piperacillin/tazobactam in the treatment of severe skin and soft-tissue infections in adults at a Veterans Affairs medical center.	2002 Jan	11833836
[Piperacillin-tazobactam in the treatment of severe nosocomial infections].	2002 Mar	11942173
Substitution of Met-69 by Ala or Gly in TEM-1 beta-lactamase confer an increased susceptibility to clavulanic acid and other inhibitors.	2002 May 21	12052544
Influence of a new prophylactic antibiotic therapy on the incidence of liver abscesses after chemoembolization treatment of liver tumors.	2002 Nov	12427817
Antimicrobial prophylaxis for transrectal prostatic biopsy: a prospective study of ciprofloxacin vs piperacillin/tazobactam.	2002 Nov	12410751
Piperacillin/Tazobactam inducing seizures in a hemodialysed patient.	2002 Oct	12400853
Susceptibility patterns of Escherichia coli: prevalence of multidrug-resistant isolates and extended spectrum beta-lactamase phenotype.	2002 Sep	12532575
Efficacy and tolerability of prophylactic treatment with intravenous piperacillin/tazobactam in patients undergoing hematopoietic stem cell transplantation.	2002 Sep	12421457
Morganella morganii causing solitary liver abscess complicated by pyopericardium and left pleural effusion in a nondiabetic patient.	2002 Sep	12380794
Pharmacodynamic profiling of continuously infused piperacillin/tazobactam against Pseudomonas aeruginosa using Monte Carlo analysis.	2002 Sep	12376031
Cefepime, piperacillin/tazobactam, gentamicin, ciprofloxacin, and levofloxacin alone and in combination against Pseudomonas aeruginosa.	2002 Sep	12376029
[Pharmacokinetics of antibiotics in inflamed and healthy lung tissue].	2003	13677255
Bacteraemia and sinusitis due to Flavimonas oryzihabitans infection.	2003	12953957
Ertapenem once a day versus piperacillin-tazobactam every 6 hours for treatment of acute pelvic infections: a prospective, multicenter, randomized, double-blind study.	2003	12839630
[Carbapenem antibiotic ertapenem in the treatment of extrahospital intraabdominal infections].	2003	12744138
Thrombocytosis under ciprofloxacin and tazobactam/piperacillin.	2003 Aug	12944250
Sciatic nerve palsy as presenting sign of a perianal abscess.	2003 Feb	12639627
Current status of drug resistance among gram-negative bacilli isolated from admitted cases in a tertiary care centre.	2003 Jan	12693450
Positive direct antiglobulin tests and haemolytic anaemia following therapy with the beta-lactamase inhibitor, tazobactam, may also be associated with non-immunologic adsorption of protein onto red blood cells.	2003 Jul	12823734
Penetration of piperacillin and tazobactam into pneumonic human lung tissue measured by in vivo microdialysis.	2003 Jun	12814459
Piperacillin-tazobactam is more effective than ceftriaxone plus gentamicin in febrile neutropenic patients with hematological malignancies: a randomized comparison.	2003 Jun	12690546
Piperacillin induced bone marrow suppression: a case report.	2003 Jun 5	12791166
[beta-Lactamase-inhibitor combinations].	2003 Mar	12717975
Role of pharmacodynamics in designing dosage regimens for beta-lactams.	2003 May	12802841
[Assay of Acinetobacter SPP drug-resistance by Kirby-Bauer and Etest method].	2003 May	12754133
Antimicrobial therapy of unexplained fever in neutropenic patients--guidelines of the Infectious Diseases Working Party (AGIHO) of the German Society of Hematology and Oncology (DGHO), Study Group Interventional Therapy of Unexplained Fever, Arbeitsgemeinschaft Supportivmassnahmen in der Onkologie (ASO) of the Deutsche Krebsgesellschaft (DKG-German Cancer Society).	2003 Oct	13680173
Intracameral antibiotic agents for endophthalmitis prophylaxis: a pharmacokinetic model.	2003 Sep	14522303
Severe acute respiratory syndrome: clinical outcome and prognostic correlates.	2003 Sep	14519241

Patents

Sample Use Guides

In Vivo Use Guide

The usual daily dose of Zosyn for adults is 3.375 g every 6 h totaling 13.5 g (12.0 g piperacillin/1.5 g tazobactam). Initial treatment of nosocomial pneumonia should start with Zosyn at a dosage of 4.5 g every 6 h plus an aminoglycoside, totaling 18.0 g (16.0 g piperacillin/2.0 g tazobactam). For children with appendicitis and/or peritonitis the recommended Zosyn dosage is 100 mg piperacillin/12.5 mg tazobactam/kg every 8 h in pediatric patients 9 months of age and older. For pediatric patients 2 to 9 months of age, the recommended dosage is 80 mg piperacillin/10 mg tazobactam/kg, every 8 h. The recommended dosage regimen of Zerbaxa is 1.5 g (ceftolozane 1 g and tazobactam 0.5 g) administered every 8 h by intravenous infusion over 1 h in patients 18 years or older and with normal renal function or mild renal impairment.

Route of Administration: Intravenous

In Vitro Use Guide

In a susceptibility test the minimal inhibitory concentration of 4 ug/ml tazobactam in combination with serial dilutions of piperacillin were <16 mcg/ml for susceptible strains of Enterobacteriaceae, Pseudomonas aeruginosa and Acinetobacter baumannii, <1 mcg/ml for susceptible strains of Haemophilus influenzae, <32 mcg/ml for susceptible strains of Bacteroides fragilis group.

Name

Type

Language

TAZOBACTAM

Official Name

English

NSC-759887

Code

English

TAZOBACTAM [WHO-DD]

Common Name

English

TAZOBACTAM [MI]

Common Name

English

TAZOBACTAM [INN]

Common Name

English

CL 298,741

Code

English

TAZOBACTAM [JAN]

Common Name

English

YTR-830H

Code

English

TAZOBACTAM [USP]

Common Name

English

TAZOBACTAM [USP MONOGRAPH]

Common Name

English

TAZOBACTAM [USAN]

Common Name

English

TAZOBACTAM [USP-RS]

Common Name

English

Classification Tree Code System Code

LIVERTOX

924