TAZOBACTAM HEMIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C10H12N4O5S.H2O
Molecular Weight	618.597
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[H][C@@]12CC(=O)N1[C@@H](C(O)=O)[C@](C)(CN3C=CN=N3)S2(=O)=O.[H][C@@]45CC(=O)N4[C@@H](C(O)=O)[C@](C)(CN6C=CN=N6)S5(=O)=O

InChI

InChIKey=BULFSGHLDZFFAI-WNEKGKLGSA-N

InChI=1S/2C10H12N4O5S.H2O/c2*1-10(5-13-3-2-11-12-13)8(9(16)17)14-6(15)4-7(14)20(10,18)19;/h2*2-3,7-8H,4-5H2,1H3,(H,16,17);1H2/t2*7-,8+,10+;/m11./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 8297		0.01 µM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Intra-abdominal infections 49 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8429	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 80 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8429	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 8429	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 90 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050684s084s086,050750s034s035lbl.pdf	Curative	Approved 8429	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 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206829s003lbl.pdf	Curative	Approved 8429	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
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 21 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599 OAT3 642 CYP1A2 1524 CYP2B6 810 CYP2C8 911 CYP2C19 1478 P-gp 1461 OATP1B1 788 OATP1B3 706 OCT1 512 OCT2 647 BCRP 699 BSEP 402	OAT1 326 OAT3 339 P-gp 1537

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
BCRP 773	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
BSEP 403	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
BSEP 403	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OAT3 644	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
OATP1B1 803	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OATP1B3 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
OCT2 648	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
P-gp 1650	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no	tazobactam M1 metabolite 3
CYP1A2 1692	inhibitor 3277 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 715	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	weak
OCT1 543	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	weak
CYP3A4 1925	inhibitor 3277 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 1692	supressor 155 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes
CYP1A2 1692	supressor 155 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
CYP2B6 1001	supressor 155 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
CYP3A4 1925	supressor 155 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes
CYP3A4 1925	supressor 155 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
OAT1 603	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	yes	tazobactam M1 metabolite 3
OAT1 603	inhibitor 3277 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 644	inhibitor 3277 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 1537	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/206829Orig1s000ClinPharmR.pdf	no
OAT1 326	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/29277663/	yes
OAT3 339	substrate 3367 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
De-escalation antimicrobial chemotherapy in critically III patients: pros and cons.	2001 Nov	11936369
[Identification and susceptibility to antimicrobial agents of strictly anaerobic bacteria isolated from hospitalized patients].	2002	12632658
[Candida parapsilosis endocarditis after prolonged antibiotic therapy].	2002 Apr	14606382
Gateways to Clinical Trials.	2002 Apr	12087878
Successful medical management of emphysematous pyelonephritis.	2002 Aug 15	12208398
[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
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
Pharmacokinetics and pharmacodynamics of piperacillin/tazobactam when administered by continuous infusion and intermittent dosing.	2002 Jul	12182254
Geographic variations in activity of broad-spectrum beta-lactams against Pseudomonas aeruginosa: summary of the worldwide SENTRY Antimicrobial Surveillance Program (1997-2000).	2002 Jul	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 Jul	12096010
Development and optimization of a reversed-phase high-performance liquid chromatographic method for the determination of piperacillin and tazobactam in tazocin injectable powder.	2002 Jul 31	12093510
Ertapenem once daily versus piperacillin-tazobactam 4 times per day for treatment of complicated skin and skin-structure infections in adults: results of a prospective, randomized, double-blind multicenter study.	2002 Jun 1	12015692
[Piperacillin-tazobactam in the treatment of severe nosocomial infections].	2002 Mar	11942173
Pharmacokinetic and pharmacodynamic evaluation of two dosing regimens for piperacillin-tazobactam.	2002 May	12013355
Comparative pharmacokinetic and pharmacodynamic profile of piperacillin/tazobactam 3.375G Q4H and 4.5G Q6H.	2002 May	12011536
[Piperacillin/tazobactam--Tazocin. A penicillin-based alternative to 3rd generation cephalosporins and carbapenems].	2002 May 13	12043402
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
Two cases of immune haemolytic anaemia, associated with anti-piperacillin, detected by the 'immune complex' method.	2002 Oct	12366773
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
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
Understanding resistance to beta-lactams and beta-lactamase inhibitors in the SHV beta-lactamase: lessons from the mutagenesis of SER-130.	2003 Dec 26	14534312
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
[Phenotypes of beta-lactam resistance in the genus Aeromonas].	2003 Jul	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 Jul	12823734
Risk factors for piperacillin/tazobactam-resistant Escherichia coli in ICU patients: a clinical study.	2003 Jul	12774156
[New Beta-lactam agent in the treatment of intra-abdominal sepsis: double blind and randomized stage III study of ertapenem versus piperacillin/tazobactam].	2003 Jul-Sep	14532920
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
Variable susceptibility to piperacillin/tazobactam amongst Klebsiella spp. with extended-spectrum beta-lactamases.	2003 Mar	12615861
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
Efficacy of ertapenem in the treatment of serious infections caused by Enterobacteriaceae: analysis of pooled clinical trial data.	2003 May	12697633
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 HEMIHYDRATE

Common Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3-METHYL-7-OXO-3-(1H-1,2,3-TRIAZOL-1-YLMETHYL)-, 4,4-DIOXIDE, HYDRATE (2:1), (2S,3S,5R)-

Systematic Name

English

Code System Code Type Description

FDA UNII

2YRJ6OXK1M

Created by admin on Sat Dec 16 09:16:28 GMT 2023 , Edited by admin on Sat Dec 16 09:16:28 GMT 2023

PRIMARY

CAS

428863-55-2

Created by admin on Sat Dec 16 09:16:28 GMT 2023 , Edited by admin on Sat Dec 16 09:16:28 GMT 2023

PRIMARY

SMS_ID

300000047633

Created by admin on Sat Dec 16 09:16:28 GMT 2023 , Edited by admin on Sat Dec 16 09:16:28 GMT 2023

PRIMARY

PUBCHEM

133082183

Created by admin on Sat Dec 16 09:16:28 GMT 2023 , Edited by admin on Sat Dec 16 09:16:28 GMT 2023

PRIMARY

ACTIVE MOIETY


					SE10G96M8W

TAZOBACTAM

SUBSTANCE RECORD


					2YRJ6OXK1M

TAZOBACTAM HEMIHYDRATE

Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

F_unbound

Drug as perpetrator