nalidixic acid 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
antibacterials, nalidixic acid derivatives 1875 389-08-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nalidixic acid
  • nalidic acid
  • nalidixinic acid
  • nalidixate
  • nalidixic acid sodium
  • nalidixic acid sodium salt
A synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA GYRASE.
  • Molecular weight: 232.24
  • Formula: C12H12N2O3
  • CLOGP: 1.02
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 70.50
  • ALOGS: -2
  • ROTB: 2
  • Status: OFM
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
4 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.43 mg/mL Bocci G, Oprea TI, Benet LZ
MRTD (Maximum Recommended Therapeutic Daily Dose) 287.20 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 96 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 0.176 Moderate 0.72
caco2-efflux Caco-2 efflux ratio (BA/AB) 1.102 Moderate 0.72
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 81.283 10^-6 cm/s Moderate 0.72
dh-clint Dog hepatocyte intrinsic clearance 8.035 uL/min/10^6 cells Moderate 0.72
dppb Dog plasma protein binding (% unbound) 32.320 % Moderate 0.72
fcs-ppb Fetal calf serum protein binding (% unbound) 36.370 % Moderate 0.72
herg hERG pIC50 4.310 pIC50 Moderate 0.72
hh-clint Human hepatocyte intrinsic clearance 1.191 uL/min/10^6 cells Moderate 0.72
hlm-clint Human liver microsomal intrinsic clearance 3.420 uL/min/mg protein Moderate 0.72
hppb Human plasma protein binding (% unbound) 14.120 % Moderate 0.72
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,ERBB2,GRK2,MAP3K21,MAPK7,NTRK2,PDK1,PDK2,PIK3CB,PIK3CD,PRKDC,SIK2,STK33,TEK 24
kinase-selectivity-class ACVR2A,ACVR2B,AXL,BRAF,CDK9,DDR1,DYRK1B,EIF2AK3,GRK2,MAP2K6,MAPK7,PIK3CB,PIK3CD,PIK3CG,PRKDC,STK33,SYK,TEK,TGFBR1,TTK 20
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 2.213 Moderate 0.72
mh-clint Mouse hepatocyte intrinsic clearance 13.996 Moderate 0.72
mppb Mouse plasma protein binding (% unbound) 30.580 Moderate 0.72
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 1.954 Moderate 0.72
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 20.040 % Moderate 0.72
rh-clint Rat hepatocyte intrinsic clearance 4.853 uL/min/10^6 cells Moderate 0.72
rh-fuinc Rat hepatocyte fraction unbound in incubation 87.570 % Moderate 0.72
rppb Rat plasma protein binding (% unbound) 6.700 % Moderate 0.72
solubility-dd Solubility at pH 7.4 in DMSO 959.401 uM Moderate 0.72

Approvals:

DateAgencyCompanyOrphan
March 6, 1964 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Idiopathic intracranial hypertension 26.26 23.32 3 3 3578 90624863

FDA Adverse Event Reporting System (Male)

None

FDA Adverse Event Reporting System (Geriatric)

None

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC J01MB02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIBACTERIALS FOR SYSTEMIC USE
QUINOLONE ANTIBACTERIALS
Other quinolones
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000900 Anti-Bacterial Agents
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D059005 Topoisomerase II Inhibitors
CHEBI has role CHEBI:33281 antimicrobial agent
CHEBI has role CHEBI:33282 antibacterial agent
CHEBI has role CHEBI:36047 antibacterial drug
CHEBI has role CHEBI:59517 DNA synthesis inhibitor

Related Drugs by ATC class:

J01MB Other quinolones 7 drugs
cinoxacinflumequinenemonoxacinoxolinic acidpipemidic acidpiromidic acidrosoxacin

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Bacterial urinary infection indication 312124009
Disorder of the central nervous system contraindication 23853001 DOID:331
Tendinitis contraindication 34840004 DOID:971
Acute nephropathy contraindication 58574008
Anemia due to enzyme deficiency contraindication 111577008
Deficiency of glucose-6-phosphate dehydrogenase contraindication 124134002 DOID:2862
Seizure disorder contraindication 128613002
Disease of liver contraindication 235856003 DOID:409
Peripheral nerve disease contraindication 302226006
Pseudomembranous enterocolitis contraindication 397683000
Traumatic rupture of tendon contraindication 415749005
Porphyria contraindication 418470004
Severe Cerebral Arteriosclerosis contraindication




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.27 acidic
pKa2 0.86 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
5-hydroxytryptamine receptor 2B GPCR IC50 5.10 WOMBAT-PK
Pyruvate kinase PKM Enzyme IC50 4.28 CHEMBL
DNA gyrase Enzyme INHIBITOR CHEMBL CHEMBL

External reference:

IDSource
4018247 VUID
N0000146578 NUI
D00183 KEGG_DRUG
4018247 VANDF
C0027353 UMLSCUI
CHEBI:100147 CHEBI
NIX PDB_CHEM_ID
CHEMBL5 ChEMBL_ID
DB00779 DRUGBANK_ID
D009268 MESH_DESCRIPTOR_UI
4421 PUBCHEM_CID
12773 IUPHAR_LIGAND_ID
1450 INN_ID
3B91HWA56M UNII
618425 RXNORM
2063 MMSL
5148 MMSL
d00157 MMSL
002860 NDDF
387261006 SNOMEDCT_US
47602007 SNOMEDCT_US

Pharmaceutical products:

None