TAZOBACTAM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12N4O5S
Molecular Weight	300.291
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@]2(CN1C=CN=N1)[C@@H](N3[C@@H](CC3=O)S2(=O)=O)C(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

Molecular Formula	C10H12N4O5S
Molecular Weight	300.291
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 11 Target ID: CHEMBL2364670 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206829s003lbl.pdf	Inhibitor 8504		0.01 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Intra-abdominal infections 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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 1993
Skin and skin structure infections 81 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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 1993
Female pelvic infections 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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 1993
Pneumonia 91 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8583	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 1993
Complicated urinary tract infections 12 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206829s003lbl.pdf	Curative	Approved 8583	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 2014

C_max

Value	Dose	Co-administered	Analyte	Population
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 inflammatory exudate	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
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
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
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 inflammatory exudate	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
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
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
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 inflammatory exudate	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
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
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 Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/	healthy, 36 Health Status: healthy Age Group: 36 Sex: M 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 Sources: https://pubmed.ncbi.nlm.nih.gov/29517862/	healthy, 39 Health Status: healthy Age Group: 39 Sex: M 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	Other AEs: Nausea, Headache... Other AEs: 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%) Anxiety (0.2%) Dizziness (1.1%) Hypotension (0.4%) Atrial fibrillation (0.2%) Rash (0.9%) 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206829lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult 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

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
supressor 22 inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 725 OAT3 747 CYP1A2 2153 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 P-gp 1741 OATP1B1 1079 OATP1B3 961 OCT1 620 OCT2 779 BCRP 910 BSEP 550	OAT1 395 OAT3 391 P-gp 2052

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
BSEP 554	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
BSEP 554	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP1A2 2333	inhibitor 4027 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 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	weak
OCT1 656	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	weak
CYP3A4 2633	inhibitor 4027 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 2333	supressor 160 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes
CYP1A2 2333	supressor 160 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
CYP2B6 1160	supressor 160 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
CYP3A4 2633	supressor 160 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes
CYP3A4 2633	supressor 160 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
OAT1 730	inhibitor 4027 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 749	inhibitor 4027 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 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/29277663/	yes
OAT3 391	substrate 4014 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
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
MolPort	MolPort-002-500-123	https://www.molport.com/shop/molecule-link/MolPort-002-500-123
ZINC	ZINC000003787060	http://zinc15.docking.org/substances/ZINC000003787060

PubMed

Title	Date	PubMed
Understanding resistance to beta-lactams and beta-lactamase inhibitors in the SHV beta-lactamase: lessons from the mutagenesis of SER-130.	2003-12-26	14534312
[New Beta-lactam agent in the treatment of intra-abdominal sepsis: double blind and randomized stage III study of ertapenem versus piperacillin/tazobactam].	2003-10-09	14532920
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).	2003-10	13680173
Intracameral antibiotic agents for endophthalmitis prophylaxis: a pharmacokinetic model.	2003-09	14522303
Severe acute respiratory syndrome: clinical outcome and prognostic correlates.	2003-09	14519241
Thrombocytosis under ciprofloxacin and tazobactam/piperacillin.	2003-08	12944250
[Phenotypes of beta-lactam resistance in the genus Aeromonas].	2003-07	14567197
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.	2003-07	12823734
Risk factors for piperacillin/tazobactam-resistant Escherichia coli in ICU patients: a clinical study.	2003-07	12774156
Piperacillin induced bone marrow suppression: a case report.	2003-06-05	12791166
Penetration of piperacillin and tazobactam into pneumonic human lung tissue measured by in vivo microdialysis.	2003-06	12814459
Piperacillin-tazobactam is more effective than ceftriaxone plus gentamicin in febrile neutropenic patients with hematological malignancies: a randomized comparison.	2003-06	12690546
Role of pharmacodynamics in designing dosage regimens for beta-lactams.	2003-05	12802841
[Assay of Acinetobacter SPP drug-resistance by Kirby-Bauer and Etest method].	2003-05	12754133
Efficacy of ertapenem in the treatment of serious infections caused by Enterobacteriaceae: analysis of pooled clinical trial data.	2003-05	12697633
[beta-Lactamase-inhibitor combinations].	2003-03	12717975
Variable susceptibility to piperacillin/tazobactam amongst Klebsiella spp. with extended-spectrum beta-lactamases.	2003-03	12615861
Sciatic nerve palsy as presenting sign of a perianal abscess.	2003-02	12639627
Current status of drug resistance among gram-negative bacilli isolated from admitted cases in a tertiary care centre.	2003-01	12693450
[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
Localised necrosis of scrotum (Fournier's gangrene) in a spinal cord injury patient - a case report.	2002-12-05	12466026
[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].	2002-12	12666475
Postoperative infection with group A beta-hemolytic Streptococcus after blepharoplasty.	2002-12	12470763
Biochemical analysis of the ceftazidime-hydrolysing extended-spectrum beta-lactamase CTX-M-15 and of its structurally related beta-lactamase CTX-M-3.	2002-12	12461028
Influence of a new prophylactic antibiotic therapy on the incidence of liver abscesses after chemoembolization treatment of liver tumors.	2002-11	12427817
Antimicrobial prophylaxis for transrectal prostatic biopsy: a prospective study of ciprofloxacin vs piperacillin/tazobactam.	2002-11	12410751
Piperacillin/Tazobactam inducing seizures in a hemodialysed patient.	2002-10	12400853
Two cases of immune haemolytic anaemia, associated with anti-piperacillin, detected by the 'immune complex' method.	2002-10	12366773
General microbiology and in vitro susceptibility of anaerobes isolated from complicated skin and skin-structure infections in patients enrolled in a comparative trial of ertapenem versus piperacillin-tazobactam.	2002-09-01	12173120
Susceptibility patterns of Escherichia coli: prevalence of multidrug-resistant isolates and extended spectrum beta-lactamase phenotype.	2002-09	12532575
Efficacy and tolerability of prophylactic treatment with intravenous piperacillin/tazobactam in patients undergoing hematopoietic stem cell transplantation.	2002-09	12421457
Morganella morganii causing solitary liver abscess complicated by pyopericardium and left pleural effusion in a nondiabetic patient.	2002-09	12380794
Pharmacodynamic profiling of continuously infused piperacillin/tazobactam against Pseudomonas aeruginosa using Monte Carlo analysis.	2002-09	12376031
Cefepime, piperacillin/tazobactam, gentamicin, ciprofloxacin, and levofloxacin alone and in combination against Pseudomonas aeruginosa.	2002-09	12376029
Successful medical management of emphysematous pyelonephritis.	2002-08-15	12208398
Molecular dynamics at the root of expansion of function in the M69L inhibitor-resistant TEM beta-lactamase from Escherichia coli.	2002-08-14	12167037
New and rapid fully automated method for determination of tazobactam and piperacillin in fatty tissue and serum by column-switching liquid chromatography.	2002-08-05	12113978
Development and optimization of a reversed-phase high-performance liquid chromatographic method for the determination of piperacillin and tazobactam in tazocin injectable powder.	2002-07-31	12093510
Pharmacokinetics and pharmacodynamics of piperacillin/tazobactam when administered by continuous infusion and intermittent dosing.	2002-07	12182254
Infecting one animal with two different strains of the same bacteria may cause misleading results.	2002-07	12138335
Geographic variations in activity of broad-spectrum beta-lactams against Pseudomonas aeruginosa: summary of the worldwide SENTRY Antimicrobial Surveillance Program (1997-2000).	2002-07	12106958
Cefepime plus amikacin versus piperacillin-tazobactam plus amikacin for initial antibiotic therapy in haematology patients with febrile neutropenia: results of an open, randomized, multicentre trial.	2002-07	12096010
Emerging antimicrobial resistances among Proteus mirabilis in Europe: report from the MYSTIC Program (1997-2001). Meropenem Yearly Susceptibility Test Information Collection.	2002-06	12120879
[Candida parapsilosis endocarditis after prolonged antibiotic therapy].	2002-04	14606382
[A multicenter clinical trial of piperacillin/tazobactam in burn infection].	2002-04	12515649
[Study on water of crystallization in tazobactam].	2002-02	12579963
[Identification and susceptibility to antimicrobial agents of strictly anaerobic bacteria isolated from hospitalized patients].	2002	12632658

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:11:28 GMT 2025` Edited by `admin` on `Mon Mar 31 18:11:28 GMT 2025`
Record UNII	SE10G96M8W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TAZOBACTAM

Official Name

English

CL 298,741

Preferred Name

English

NSC-759887

Code

English

TAZOBACTAM [MI]

Common Name

English

tazobactam [INN]

Common Name

English

TAZOBACTAM [JAN]

Common Name

English

TAZOBACTAM [USP IMPURITY]

Common Name

English

YTR-830H

Code

English

Tazobactam [WHO-DD]

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

NBK548825