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Compound Detail

CHEMBL891

CLOXACILLIN
💊 Approved Drug
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💊 Approved Drug
Cc1onc(-c2ccccc2Cl)c1C(=O)N[C@@H]1C(=O)N2[C@@H]1SC(C)(C)[C@@H]2C(=O)O

Basic Information

ChEMBL ID CHEMBL891
Name CLOXACILLIN
Phase Approved
Structure Type MOL
InChI Key LQOLIRLGBULYKD-JKIFEVAISA-N
Therapeutic ✓ Yes

Known Names

Cloxacilina Cloxacillin Cloxacilline Orbenin
7
Targets
16
Activities
2
Assay Types
3
PK Parameters
20
Publications
4
Known Names
6
Indications

Molecular Properties

435.9
MW (Da)
2.55
ALogP
6
HBA
2
HBD
112.7
PSA (Ų)
0.71
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1974
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -cillin
USAN Year 1963

Extended Properties

Molecular Formula C19H18ClN3O5S
MW 435.89
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -0.33

Indications

Bacterial Infections Enterobacteriaceae Infections Staphylococcal Infections Gram-Positive Bacterial Infections Mastitis Osteomyelitis

ATC Classification

J01CF02
cloxacillin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 8 meas. best 8.4
Ki 8 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
Ki 9.7 9.17 0.2 2
Efflux transporter
CHEMBL1641337
IC50 8.4 8.4 4.0 1
Class C beta-lactamase CMY-36
CHEMBL1641338
IC50 8.4 8.4 4.0 1
Unchecked
CHEMBL612545
IC50 8.4 8.4 4.0 1
Beta-lactamase ACC-4
CHEMBL5305
IC50 7.58 7.58 26.0 1
Beta-lactamase TEM
CHEMBL2065
Ki 4.89 4.89 13000.0 1
Organic anion transporter 3
CHEMBL2073672
IC50 4.51 4.51 30900.0 1
Bile salt export pump
CHEMBL6020
IC50 4.38 4.38 41570.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.6 mL.min-1.kg-1 Homo sapiens
CL 0.6 mL.min-1.kg-1 Homo sapiens
F 37.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
18519727 10.1128/aac.00123-08 Staphylococcus aureus 110
30503946 10.1016/j.ejmech.2018.11.052 Staphylococcus aureus 28
19506058 10.1128/aac.01655-08 Campylobacter jejuni 24
20211889 10.1128/aac.01677-09 Escherichia coli 20
19029333 10.1128/aac.00485-08 Acinetobacter pittii 15
17060530 10.1128/aac.00261-06 Bifidobacterium longum 15
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
17060530 10.1128/aac.00261-06 NON-PROTEIN TARGET 10
17060530 10.1128/aac.00261-06 Bifidobacterium bifidum 10
17307986 10.1128/aac.01192-06 Staphylococcus aureus 9
19506059 10.1128/aac.00371-09 Salmonella enterica 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
17060530 10.1128/aac.00261-06 Bifidobacterium breve 8
20070106 10.1021/jm901371v Homo sapiens 7
19506058 10.1128/aac.01655-08 Campylobacter coli 6
23344796 10.1124/dmd.112.049569 Organic anion transporter 3 5
17060530 10.1128/aac.00261-06 Bifidobacterium thermophilum 4
27575438 10.1021/acs.jmedchem.6b00580 Staphylococcus aureus 4
20869876 10.1016/j.bmc.2010.08.052 Albumin 4

Data from ChEMBL 36 via Core Engine