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Compound Detail

CHEMBL5

NALIDIXIC ACID
💊 Approved Drug
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💊 Approved Drug
CCn1cc(C(=O)O)c(=O)c2ccc(C)nc21

Basic Information

ChEMBL ID CHEMBL5
Name NALIDIXIC ACID
Phase Approved
Structure Type MOL
InChI Key MHWLWQUZZRMNGJ-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acide nalidixique Acido nalidixico Mictral Nalidixane Nalidixate Nalidixic acid Nalix Neg gram Neggram Negram NSC-82174 Uriben +3 more
4
Targets
23
Activities
1
Assay Types
4
PK Parameters
20
Publications
15
Known Names
2
Indications
1
Mechanisms

Molecular Properties

232.2
MW (Da)
1.42
ALogP
4
HBA
1
HBD
72.2
PSA (Ų)
0.85
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Discontinued
Chirality Achiral

Routes of Administration

Oral

Flags

Natural Product
USAN Stem nal-
USAN Year 1962

Extended Properties

Molecular Formula C12H12N2O3
MW 232.24
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -0.98

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial DNA gyrase inhibitor INHIBITOR Bacterial DNA gyrase

Indications

Bacterial Infections Osteomyelitis

ATC Classification

J01MB02
nalidixic acid
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 23 meas. best 4.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Pyruvate kinase PKM
CHEMBL1075189
IC50 4.28 4.28 53000.0 3
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.24 4.24 57500.0 1
Unchecked
CHEMBL612545
IC50 4.22 4.14 60380.0 3
DNA gyrase
CHEMBL2094139
IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 3.46 uL.min-1.(10^6cells)-1 Homo sapiens
CL 4.0 mL.min-1.g-1 Homo sapiens
F 60.0 % Eutheria
T1/2 1.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
17908946 10.1128/aac.00294-07 Salmonella enterica subsp. enterica 55
17043131 10.1128/aac.00600-06 Salmonella typhimurium 44
18443112 10.1128/aac.00084-08 Salmonella typhimurium 41
18505849 10.1128/aac.00151-08 Klebsiella pneumoniae 33
18490500 10.1128/aac.01686-07 Escherichia coli 33
19104017 10.1128/aac.01005-08 Salmonella enteritidis 28
19414571 10.1128/aac.00023-09 Bordetella pertussis 23
19114678 10.1128/aac.01260-08 NON-PROTEIN TARGET 20
18180352 10.1128/aac.01094-07 Proteus mirabilis 19
18725440 10.1128/aac.00082-08 Streptococcus pneumoniae 19
19364872 10.1128/aac.01722-08 Escherichia coli 19
19721064 10.1128/aac.00787-09 Escherichia coli 18
17116660 10.1128/aac.00972-06 Streptococcus suis 18
20679507 10.1128/aac.01607-09 Klebsiella pneumoniae 17
19596880 10.1128/aac.00121-09 Escherichia coli 17
17283196 10.1128/aac.01437-06 Haemophilus influenzae 17
17220404 10.1128/aac.01128-06 Escherichia coli 17
20696876 10.1128/aac.00139-10 Escherichia coli 16
17893152 10.1128/aac.00830-07 Pseudomonas aeruginosa 16
18519713 10.1128/aac.01341-07 Enterobacter cloacae 16

Data from ChEMBL 36 via Core Engine