Compound Detail

CHEMBL777

CLAVULANIC ACID

💊 Approved Drug

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💊 Approved Drug

O=C(O)[C@H]1/C(=C/CO)O[C@@H]2CC(=O)N21

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL777
Name	CLAVULANIC ACID
Phase	Approved
Structure Type	MOL
InChI Key	HZZVJAQRINQKSD-PBFISZAISA-N
Therapeutic	✓ Yes

Known Names

Acide clavulanique Acido clavulanico BRL 14151 BRL-14151 Clavulanate Clavulanic acid RX-10100 Serdaxin

Targets

102

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

199.2

MW (Da)

-1.10

ALogP

HBA

HBD

87.1

PSA (Å²)

0.55

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1984
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Natural Product

USAN Year

1986

Extended Properties

Molecular Formula	C8H9NO5
MW	199.16
Aromatic Rings	0
Heavy Atoms	14
NP-Likeness	2.19

Indications

Bronchitis Bronchitis, Chronic Cholecystitis Clostridium Infections Cystitis, Hemorrhagic Enterobacteriaceae Infections Helicobacter Infections Hernia Infections Influenza, Human Otitis Media Otitis Media Otitis Media, Suppurative Pneumonia Severe Acute Respiratory Syndrome Sinusitis Urinary Bladder Neoplasms Urinary Tract Infections Asthma Buruli Ulcer

Activity Summary

IC50 80 meas. best 8.4

Ki 22 meas. best 7.7

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Unchecked CHEMBL612545	IC50	8.4	6.6383	4.0	36
Gil1 CHEMBL1075063	IC50	8.05	8.05	9.0	1
Beta-lactamase CTX-M CHEMBL6131	IC50	8.05	8.05	9.0	1
Extended-spectrum beta-lactamase CTX-M-53 CHEMBL1667678	IC50	8.0	8.0	10.0	1
Beta-lactamase CHEMBL2026	IC50	7.82	7.82	15.0	2
Unchecked CHEMBL612545	Ki	7.7	5.3873	20.0	11
Beta-lactamase SHV-55 CHEMBL1255144	IC50	7.7	7.7	20.0	1
Beta-lactamase SHV-1 CHEMBL5956	IC50	7.55	7.535	28.0	2
Beta-lactamase TEM CHEMBL2364670	IC50	7.53	7.53	29.5	1
Beta-lactamase TEM CHEMBL2065	IC50	7.52	6.47	30.0	7
Beta-lactamase CHEMBL3308938	IC50	7.44	7.44	36.0	1
Escherichia coli CHEMBL354	IC50	7.4	7.4	40.0	1
Beta-lactamase SCO-1 CHEMBL1075073	IC50	7.16	7.16	70.0	1
Beta-lactamase CHEMBL4114	IC50	7.1	7.1	80.0	1
Beta-lactamase CHEMBL5439	IC50	7.07	7.07	85.0	1
Beta-lactamase GES-13 CHEMBL1250341	IC50	7.0	7.0	100.0	1
Beta-lactamase CHEMBL3885668	IC50	7.0	7.0	100.0	1
Beta-lactamase bla(BEL1) CHEMBL3885670	IC50	7.0	7.0	100.0	1
Beta-lactamase SHV-1 CHEMBL5094	IC50	6.77	6.77	170.0	2
Beta-lactamase TEM CHEMBL2065	Ki	6.1	6.1	800.0	1
Beta-lactamase CHEMBL5031	IC50	6.1	6.1	800.0	1
Beta-lactamase SHV-72 CHEMBL1255121	IC50	5.76	5.76	1720.0	1
Class D beta-lactamase CHEMBL1255145	IC50	5.7	5.7	2000.0	1
Beta-lactamase OXA-1 CHEMBL4951	IC50	5.5	5.5	3200.0	1
Beta-lactamase TEM-125 CHEMBL5041	IC50	5.07	5.07	8600.0	1
Carbapenem-hydrolyzing beta-lactamase KPC CHEMBL6132	IC50	4.98	4.98	10500.0	1
Carbapenem-hydrolyzing beta-lactamase KPC CHEMBL6132	Ki	4.96	4.96	11000.0	1
Beta-lactamase SHV-5 CHEMBL1075174	Ki	4.6	4.6	25360.0	1
Carbapenem-hydrolizing beta-lactamase SFC-1 CHEMBL5042	IC50	4.14	4.14	72800.0	1
Beta-lactamase class C CHEMBL3499	IC50	4.0	4.0	100000.0	1
Enterobacter cloacae CHEMBL349	IC50	4.0	4.0	100000.0	1
Beta-lactamase CHEMBL2725	IC50	4.0	4.0	100000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	4700.0	ng.hr.mL-1	-
AUC	4500.0	ng.hr.mL-1	-
CL	3.1	mL.min-1.kg-1	Homo sapiens
CL	1.8	mL.min-1.kg-1	Homo sapiens
CL	3.1	mL.min-1.kg-1	Homo sapiens
CL	3.1	mL.min-1.kg-1	Homo sapiens
Cmax	10544.29	nM	-
Cmax	10544.29	nM	-
F	75.0	%	Homo sapiens
Fu	0.91	-	Homo sapiens
Fu	0.91	-	Homo sapiens
MRT	1.0	hr	Homo sapiens
T1/2	2.0	hr	-
T1/2	1.0	hr	-
T1/2	0.9	hr	Homo sapiens
Tmax	1.5	hr	-
Tmax	1.5	hr	-

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Unchecked	IC50	=	4.0	nM	8.4	Inhibition of beta-lactamase SHV-4 assessed as nitrocefin hydrolysis after 5 min...	20921316
Gil1	IC50	=	9.0	nM	8.05	Inhibition of Citrobacter gillenii CIP 106783 Beta-lactamase GIL1 expressed in E...	17242148
Beta-lactamase CTX-M	IC50	=	9.0	nM	8.05	Inhibition of Escherichia coli CTX-M-15	17591851
Unchecked	IC50	=	10.0	nM	8.0	Inhibition of Shigella sonnei UIH-1 beta-lactamase CTX-M-64 by spectrophotometry...	18955524
Extended-spectrum beta-lactamase CTX-M-53	IC50	=	10.0	nM	8.0	Inhibition of Salmonella enterica serotype Westhampton beta-lactamase CTX-M-53	19273683
Unchecked	IC50	=	12.0	nM	7.92	Inhibition of beta-lactamase CTX-M-15 assessed as nitrocefin hydrolysis after 5 ...	20921316
Unchecked	IC50	=	12.0	nM	7.92	Inhibition of bacterial SHV-5 using cefotaxime as substrate preincubated for 15 ...	31765155
Beta-lactamase	IC50	=	15.0	nM	7.82	Inhibitory activity against Escherichia coli TEM-3 Beta-lactamase	9767633
Beta-lactamase	IC50	=	15.0	nM	7.82	Inhibitory activity against Escherichia coli TEM-3 Beta-lactamase	9767633
Beta-lactamase SHV-55	IC50	=	20.0	nM	7.7	Inhibition of Klebsiella pneumoniae Beta-Lactamase SHV-55	18316524
Unchecked	IC50	=	20.0	nM	7.7	Inhibition of Escherichia coli DH5alpha beta-lactamase TEM-12	17709463
Unchecked	IC50	=	20.0	nM	7.7	Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM28	17220412
Unchecked	Ki	=	20.0	nM	7.7	Inhibition of Escherichia coli recombinant TEM-10 assessed as substrate nitrocef...	25782055
Unchecked	IC50	=	25.0	nM	7.6	Inhibition of Escherichia coli BL21(DE3) beta-lactamase TEM1	17220412
Unchecked	Ki	=	27.0	nM	7.57	Inhibition of Escherichia coli recombinant CTX-M-15 assessed as substrate nitroc...	25782055
Unchecked	IC50	=	28.0	nM	7.55	Inhibition of Klebsiella pneumoniae Beta-lactamase SHV-1	19075067
Beta-lactamase SHV-1	IC50	=	28.0	nM	7.55	Inhibition of Escherichia coli SHV1	17665896
Beta-lactamase TEM	IC50	=	29.5	nM	7.53	Cell Free Inhibition Assay: The inhibitory concentrations (IC50, [uM]) of the be...	-
Beta-lactamase TEM	IC50	=	30.0	nM	7.52	Inhibition of Escherichia coli TEM1	17665896
Unchecked	IC50	=	30.0	nM	7.52	Inhibition of Beta-lactamase TEM-1	19075067

Literature References

PubMed	DOI	Target Context	# Activities
17664320	10.1128/aac.01530-06	ADMET	49
19506058	10.1128/aac.01655-08	Campylobacter jejuni	27
31765155	10.1021/acs.jmedchem.9b01518	Unchecked	10
19506058	10.1128/aac.01655-08	Campylobacter coli	9
17709463	10.1128/aac.00614-07	Unchecked	8
23252553	10.1021/jm301490d	Unchecked	8
20921316	10.1128/aac.00568-10	Unchecked	8
20070106	10.1021/jm901371v	Homo sapiens	8
25782055	10.1021/acs.jmedchem.5b00127	Unchecked	6
17220412	10.1128/aac.01058-06	Unchecked	6
20696873	10.1128/aac.00771-10	Unchecked	6
-	10.1016/S0960-894X(01)80933-1	Beta-lactamase	5
20086146	10.1128/aac.00743-09	Unchecked	5
23252553	10.1021/jm301490d	Escherichia coli	5
3872369	10.1021/jm00382a025	Escherichia coli	4
8064298	10.1021/np50107a016	Beta-lactamase	4
20008772	10.1128/aac.00693-09	Unchecked	4
18426954	10.1124/dmd.108.020479	ADMET	4
3872369	10.1021/jm00382a025	Staphylococcus aureus	4
-	10.1016/S0960-894X(01)80506-0	Beta-lactamase	4

Data from ChEMBL 36 via Core Engine