Compound Detail

CHEMBL404

TAZOBACTAM

💊 Approved Drug

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💊 Approved Drug

C[C@]1(Cn2ccnn2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL404
Name	TAZOBACTAM
Phase	Approved
Structure Type	MOL
InChI Key	LPQZKKCYTLCDGQ-WEDXCCLWSA-N
Therapeutic	✓ Yes

Known Names

CL 298,741 CL-298741 NSC-759887 Tazobactam YTR-830H

Targets

140

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

300.3

MW (Da)

-1.52

ALogP

HBA

HBD

122.5

PSA (Å²)

0.67

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1993
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product

USAN Stem	-bactam
USAN Year	1989

Extended Properties

Molecular Formula	C10H12N4O5S
MW	300.30
Aromatic Rings	1
Heavy Atoms	20
NP-Likeness	-0.31

Indications

Bacterial Infections Abscess Cholecystitis, Acute Diabetic Foot Enterobacteriaceae Infections Hematologic Neoplasms Infections Influenza, Human Lung Diseases Pneumonia Pneumonia, Bacterial Pneumonia, Ventilator-Associated Pseudomonas Infections Pyelonephritis Sepsis Severe Acute Respiratory Syndrome Shock, Septic Urinary Tract Infections Appendicitis Communicable Diseases

ATC Classification

J01CG02

tazobactam

Level 1: ANTIINFECTIVES FOR SYSTEMIC USE

Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 113 meas. best 9.0

Ki 27 meas. best 9.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	Ki	9.4	5.9279	0.4	19
Unchecked CHEMBL612545	IC50	9.0	6.4358	1.0	43
Beta-lactamase CTX-M CHEMBL6131	IC50	8.7	8.7	2.0	1
Extended-spectrum beta-lactamase CTX-M-53 CHEMBL1667678	IC50	8.66	8.66	2.2	1
Beta-lactamase CHEMBL5439	IC50	8.4	8.4	4.0	1
Beta-lactamase SCO-1 CHEMBL1075073	IC50	8.0	8.0	10.0	1
Beta-lactamase TEM CHEMBL2065	IC50	7.77	7.2186	17.0	7
Beta-lactamase TEM CHEMBL2364670	IC50	7.76	7.76	17.2	1
IMI-1 CHEMBL5219	IC50	7.52	7.52	30.0	2
Gil1 CHEMBL1075063	IC50	7.4	7.4	40.0	1
Beta-lactamase CHEMBL3308938	IC50	7.4	7.4	40.0	1
Beta-lactamase TEM CHEMBL3652	IC50	7.22	7.22	60.0	1
Beta-lactamase GES-13 CHEMBL1250341	IC50	7.22	7.22	60.0	1
Beta-lactamase SHV-72 CHEMBL1255121	IC50	7.1	7.1	80.0	1
PER-2 beta-lactamase CHEMBL5303	IC50	7.02	7.02	96.0	1
Beta-lactamase CHEMBL2725	IC50	7.0	5.7524	100.0	17
Beta-lactamase SHV-1 CHEMBL5094	IC50	6.96	6.96	110.0	1
Class D beta-lactamase CHEMBL1255145	IC50	6.8	6.8	160.0	1
Beta-lactamase TEM CHEMBL2364670	Ki	6.72	6.72	190.0	1
Beta-lactamase CHEMBL5764	IC50	6.72	6.72	190.0	1
Beta-lactamase SHV-1 CHEMBL5956	IC50	6.65	6.65	222.0	2
Beta-lactamase TEM-125 CHEMBL5041	IC50	6.62	6.62	240.0	1
Beta-lactamase CHEMBL2026	IC50	6.6	4.9167	250.0	6
Carbapenem-hydrolyzing beta-lactamase KPC CHEMBL6132	IC50	6.43	6.43	370.0	2
Beta-lactamase CHEMBL4114	IC50	6.3	6.3	500.0	1
PenB class A beta-lactamase CHEMBL1641339	IC50	6.3	6.3	500.0	1
Beta-lactamase CHEMBL5633	IC50	6.29	6.29	510.0	1
Beta-lactamase CHEMBL5031	IC50	6.09	5.3875	820.0	4
Beta-lactamase CHEMBL1255130	IC50	6.03	6.03	930.0	1
Beta-lactamase bla(BEL1) CHEMBL3885670	IC50	5.7	5.7	2000.0	1
Beta-lactamase CHEMBL3885668	IC50	5.7	5.7	2000.0	1
Klebsiella pneumoniae CHEMBL350	IC50	5.44	5.44	3600.0	1
Beta-lactamase OXA-1 CHEMBL4951	IC50	5.32	5.32	4800.0	1
Carbapenem-hydrolizing beta-lactamase SFC-1 CHEMBL5042	IC50	5.16	5.16	6900.0	1
Carbapenem-hydrolyzing beta-lactamase KPC CHEMBL6132	Ki	4.13	4.13	74000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
T1/2	7.7	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	Ki	=	0.4	nM	9.4	Inhibition of Escherichia coli recombinant SHV-12 assessed as substrate nitrocef...	25782055
Unchecked	Ki	=	1.0	nM	9.0	Inhibition of Escherichia coli recombinant CTX-M-15 assessed as substrate nitroc...	25782055
Unchecked	IC50	=	1.0	nM	9.0	Inhibition of bacterial CTX-M-15 using cefotaxime as substrate preincubated for ...	31765155
Beta-lactamase CTX-M	IC50	=	2.0	nM	8.7	Inhibition of Escherichia coli CTX-M-15	17591851
Extended-spectrum beta-lactamase CTX-M-53	IC50	=	2.2	nM	8.66	Inhibition of Salmonella enterica serotype Westhampton beta-lactamase CTX-M-53	19273683
Beta-lactamase	IC50	=	4.0	nM	8.4	Inhibition of Bacillus clausii NR beta-lactamase BCL1 expressed in Escherichia c...	17846134
Unchecked	Ki	=	5.0	nM	8.3	Inhibition of Escherichia coli recombinant TEM-10 assessed as substrate nitrocef...	25782055
Unchecked	IC50	=	6.0	nM	8.22	Inhibition of beta-lactamase CTX-M-15 assessed as nitrocefin hydrolysis after 5 ...	20921316
Beta-lactamase SCO-1	IC50	=	10.0	nM	8.0	Inhibition of Escherichia coli beta-lactamase SCO1	17353248
Unchecked	IC50	=	14.0	nM	7.85	Inhibition of Beta-lactamase TEM-1	19075067
Unchecked	IC50	=	15.0	nM	7.82	Inhibition of bacterial SHV-5 using cefotaxime as substrate preincubated for 15 ...	31765155
Beta-lactamase TEM	IC50	=	17.0	nM	7.77	Inhibition of Escherichia coli TEM1	17665896
Beta-lactamase TEM	IC50	=	17.2	nM	7.76	Cell Free Inhibition Assay: The inhibitory concentrations (IC50, [uM]) of the be...	-
Unchecked	IC50	=	20.0	nM	7.7	Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM28	17220412
Beta-lactamase TEM	IC50	=	25.0	nM	7.6	Inhibitory activity against beta-Lactamase enzyme derived from Escherichia coli ...	-
Unchecked	Ki	=	30.0	nM	7.52	Inhibition of beta-lactamase TEM-1 after 5 seconds incubation with nitrocefin su...	20921316
Unchecked	IC50	=	30.0	nM	7.52	Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM1	17220412
IMI-1	IC50	=	30.0	nM	7.52	Inhibition of Enterobacter cloacae IMI1 beta lactamase expressed in Escherichia ...	17875998
IMI-1	IC50	=	30.0	nM	7.52	In vitro inhibitory activity against Class A (Imi-1) beta-Lactamases	15214794
Unchecked	IC50	=	30.0	nM	7.52	Inhibition of Beta-lactamase GES-2 E104, N170 mutant preincubated for 5 mins bef...	20696873

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	228
31765155	10.1021/acs.jmedchem.9b01518	Unchecked	56
19506058	10.1128/aac.01655-08	Campylobacter jejuni	26
8809160	10.1021/jm9601967	Beta-lactamase	18
20696871	10.1128/aac.00414-10	Acinetobacter baumannii	17
31269398	10.1021/acs.jmedchem.9b00735	Unchecked	12
30288219	10.1039/C8MD00342D	Unchecked	12
8809160	10.1021/jm9601967	Escherichia coli	9
19506058	10.1128/aac.01655-08	Campylobacter coli	9
20921316	10.1128/aac.00568-10	Unchecked	8
23252553	10.1021/jm301490d	Unchecked	8
20921316	10.1128/aac.00568-10	Beta-lactamase	6
17220412	10.1128/aac.01058-06	Unchecked	6
20696873	10.1128/aac.00771-10	Unchecked	6
25782055	10.1021/acs.jmedchem.5b00127	Unchecked	6
20086146	10.1128/aac.00743-09	Unchecked	5
-	10.1016/S0960-894X(01)80933-1	Beta-lactamase	5
23252553	10.1021/jm301490d	Escherichia coli	5
28994597	10.1021/acs.jmedchem.7b01164	Acinetobacter baumannii	5
20008772	10.1128/aac.00693-09	Unchecked	4

Data from ChEMBL 36 via Core Engine