U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H11N2O3.Na.H2O
Molecular Weight 272.2324
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALIDIXATE SODIUM

SMILES

O.[Na+].CCN1C=C(C([O-])=O)C(=O)C2=C1N=C(C)C=C2

InChI

InChIKey=OWEXQJSSKQXXSX-UHFFFAOYSA-M
InChI=1S/C12H12N2O3.Na.H2O/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14;;/h4-6H,3H2,1-2H3,(H,16,17);;1H2/q;+1;/p-1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C12H12N2O3
Molecular Weight 232.2353
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pmc/articles/PMC432036/pdf/pnas00033-0067.pdf

Nalidixic acid is a quinolone antibacterial indicated for the treatment of urinary tract infections. Nalidixic acid has marked antibacterial activity against gram-negative bacteria including Enterobacter species, Escherichia coli, Morganella Morganii; Proteus Mirabilis, Proteus vulgaris, and Providencia rettgeri. Pseudomonas species are generally resistant to the drug. It is suggested that nalidixic acid acts by inhibiting bacterial DNA gyrase.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Negligible amounts of nalidixic acid cross the blood brain barrier.

Originator

Approval Year

1964
102
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 110.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
NEGGRAM

Approved Use

NegGram (nalidixic acid, USP) is indicated for the treatment of urinary tract infections caused by susceptible gram-negative microorganisms, including the majority of E. Coli, Enterobacter species, Klebsiella species, and Proteus species. Disc susceptibility testing with the 30 mcg disc should be performed prior to administration of the drug, and during treatment if clinical response warrants.

Launch Date

1964
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
27.8 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7174858/
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NALIDIXIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
327.7 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7174858/
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NALIDIXIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7174858/
1 g single, oral
dose: 1 g
route of administration: Oral
experiment type: SINGLE
co-administered:
NALIDIXIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
28 g single, oral
Overdose
Dose: 28 g
Route: oral
Route: single
Dose: 28 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/500943/
healthy, 19 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/500943/
Disc. AE: Metabolic acidosis, Coma...
AEs leading to
discontinuation/dose reduction:
Metabolic acidosis (1 patient)
Coma (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/500943/
150 mg/kg single, oral
Overdose
Dose: 150 mg/kg
Route: oral
Route: single
Dose: 150 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
unhealthy, 6 months
n = 12
Health Status: unhealthy
Condition: acute bacillary dysentery
Age Group: 6 months
Sex: unknown
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
Disc. AE: Vomiting, Intracranial hypertension...
AEs leading to
discontinuation/dose reduction:
Vomiting (12 patients)
Intracranial hypertension (12 patients)
Convulsions (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21879777/
unhealthy, adult
Health Status: unhealthy
Condition: acute bacillary dysentery
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/21879777/
Other AEs: Phototoxicity...
Other AEs:
Phototoxicity
Sources:
https://pubmed.ncbi.nlm.nih.gov/21879777/
AEs

AEs

AESignificanceDosePopulation
Coma 1 patient
Disc. AE
28 g single, oral
Overdose
Dose: 28 g
Route: oral
Route: single
Dose: 28 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/500943/
healthy, 19 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/500943/
Metabolic acidosis 1 patient
Disc. AE
28 g single, oral
Overdose
Dose: 28 g
Route: oral
Route: single
Dose: 28 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/500943/
healthy, 19 years
n = 1
Health Status: healthy
Condition: suicide attempt
Age Group: 19 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/500943/
Intracranial hypertension 12 patients
Disc. AE
150 mg/kg single, oral
Overdose
Dose: 150 mg/kg
Route: oral
Route: single
Dose: 150 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
unhealthy, 6 months
n = 12
Health Status: unhealthy
Condition: acute bacillary dysentery
Age Group: 6 months
Sex: unknown
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
Vomiting 12 patients
Disc. AE
150 mg/kg single, oral
Overdose
Dose: 150 mg/kg
Route: oral
Route: single
Dose: 150 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
unhealthy, 6 months
n = 12
Health Status: unhealthy
Condition: acute bacillary dysentery
Age Group: 6 months
Sex: unknown
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
Convulsions 2 patients
Disc. AE
150 mg/kg single, oral
Overdose
Dose: 150 mg/kg
Route: oral
Route: single
Dose: 150 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
unhealthy, 6 months
n = 12
Health Status: unhealthy
Condition: acute bacillary dysentery
Age Group: 6 months
Sex: unknown
Population Size: 12
Sources:
https://pubmed.ncbi.nlm.nih.gov/1972527/
Phototoxicity
1 g 4 times / day steady, oral
Recommended
Dose: 1 g, 4 times / day
Route: oral
Route: steady
Dose: 1 g, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/21879777/
unhealthy, adult
Health Status: unhealthy
Condition: acute bacillary dysentery
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/21879777/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

OAT1
599

OAT3
642

MRP4
204

UGT1A8
36

UGT1A10
32
OAT1
326

UGT
192
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
UGT1A10
41
 inconclusive
UGT1A8
48
 inconclusive
OAT3
644
 yes [IC50 0.3 uM]
MRP4
238
 yes [IC50 4.2 uM]
OAT1
603
 yes [IC50 78.3 uM]
CYP1A2
1692
 yes [Inhibition 500 uM]
no (co-administration study)
Comment: no effects on theophylline pharmacokinetics were reported
Page: 1,6
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
OAT1
326
 likely
UGT
192
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:100147
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:100147
ChemicalBook
CB1194283
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1194283
MolPort
MolPort-001-769-233
https://www.molport.com/shop/molecule-link/MolPort-001-769-233
Selleck Chemicals
Nalidixic-acid(NegGram)
http://www.selleckchem.com/products/Nalidixic-acid(NegGram).html
ZINC
ZINC000000057421
http://zinc15.docking.org/substances/ZINC000000057421
eMolecules
529362
https://www.emolecules.com/cgi-bin/more?vid=529362
PubMed

PubMed

TitleDatePubMed
Nalidixic acid induced pseudotumour cerebri in children.
1998 Oct
[The evolution of quinolone: from nalidixic acid to the quinolones of the third generation].
2001
Molecular characterization of Salmonella weltevreden isolated from poultry: evidence of conjugal transfer of plasmid and antibiotic resistance.
2001
Drug toxicity in E. coli cells expressing human topoisomerase I.
2001
Prevalence of resistance to antimicrobials of Escherichia coli isolates from clinical sources at a private hospital in Trinidad.
2001 Apr
Synthesis and properties of dextran-nalidixic acid ester as a colon-specific prodrug of nalidixic acid.
2001 Apr
Antimicrobial susceptibility of potentially pathogenic halophilic vibrios isolated from seafood.
2001 Aug
Positive effects of some gyrase inhibitors on survival and development of Pimpla turionellae (Hymenoptera: Ichneumonidae) larvae reared on an artificial diet.
2001 Feb
Antibiotic resistance in Salmonella enterica subsp. enterica strains isolated in Poland from 1998 to 1999.
2001 Jul
Enteric fever treatment failures: a global concern.
2001 Jul-Aug
Pathogenicity and drug susceptibility of the Pasteurella anatis isolated in chickens in Taiwan.
2001 Jul-Sep
Screening of antibiotic resistant inhibitors from local plant materials against two different strains of Pseudomonas aeruginosa.
2001 Jun
A population-based case-control teratologic study of nalidixic acid.
2001 Jun
Improved agar diffusion method for detecting residual antimicrobial agents.
2001 Mar
Characterization of high-level fluoroquinolone resistance in Escherichia coli O78:K80 isolated from turkeys.
2001 Mar
Antimicrobial resistance in salmonellae from humans, food and animals in Spain in 1998.
2001 Mar
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli.
2001 Mar-Apr
Transcription of essential cell division genes is linked to chromosome replication in Escherichia coli.
2001 May
Typhoid and paratyphoid fever: a 10-year retrospective study of 41 cases in a Parisian hospital.
2001 Nov-Dec
Epidemiological analysis of Salmonella enteritidis isolates in Singapore.
2001 Oct
Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients.
2001 Oct
[Comparative study of the bacteriostatic and bactericidal activity of levofloxacin against Pasteurella strains isolated from man].
2001 Oct
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.
2001 Oct
Epidemiology of shigellosis in Lagos, Nigeria: trends in antimicrobial resistance.
2001 Sep
Media for the isolation and enumeration of bifidobacteria in dairy products.
2001 Sep 28
Effect of an efflux pump inhibitor on the MIC of nalidixic acid for Acinetobacter baumannii and Stenotrophomonas maltophilia clinical isolates.
2002 Apr
Identification of an immunodominant drug efflux pump in Burkholderia cepacia.
2002 Apr
Serovars of Salmonella isolated from Danish turkeys between 1995 and 2000 and their antimicrobial resistance.
2002 Apr 13
Time-dependent toxicity in the long-term inhibition assay with Vibrio fischeri.
2002 Feb
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.
2002 Feb
Green fluorescent protein-based biosensor for detecting SOS-inducing activity of genotoxic compounds.
2002 Jan
Emergence and rapid spread of tetracycline-resistant Vibrio cholerae strains, Madagascar.
2002 Mar
Inactivation of Escherichia coli O157:H7 on inoculated alfalfa seeds with ozonated water and heat treatment.
2002 Mar
Patents

Patents

20010006677
50
JP2001500477A
122
JP2002541233A
400
JP2009541210A
79
JPH02300140A
17
JPH04230631A
7
JPH09169668A
5
JPS5794299A
4
JPS606617A
6

Sample Use Guides

In Vivo Use Guide
1 g administered four times daily for one or two weeks (adults), 25 mg/lb/day (55 mg/kg/day), administered in four equally divided doses (pediatric use).
Route of Administration: Oral
In Vitro Use Guide
The susceptibilities of the 15-nalidixic acid susceptible and 59 nalidixic acid-resistant isolates of P.mirabilis were tested against nalidixic acid. MIC50 values were 8 mg/L and >512 mg/L, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:20 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:20 GMT 2023
Record UNII
J17QL41ZAG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NALIDIXATE SODIUM
USAN  
USAN  
Official Name English
NALIDIXATE SODIUM [USAN]
Common Name English
NALIDIXATE SODIUM MONOHYDRATE
Common Name English
1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1-ETHYL-1,4-DIHYDRO-7-METHYL-4-OXO-, SODIUM SALT, MONOHYDRATE
Common Name English
Sodium 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylate monohydrate
Systematic Name English
WIN-18320-3
Code English
WIN 18,320-3
Code English
Classification Tree Code System Code
NCI_THESAURUS C795
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
Code System Code Type Description
FDA UNII
J17QL41ZAG
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
PRIMARY
NCI_THESAURUS
C80641
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
PRIMARY
SMS_ID
300000040300
Created by admin on Fri Dec 15 15:03:21 GMT 2023 , Edited by admin on Fri Dec 15 15:03:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL5
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
PRIMARY
CAS
15769-77-4
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
PRIMARY
PUBCHEM
23675318
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID50935777
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
PRIMARY
EVMPD
SUB14627MIG
Created by admin on Fri Dec 15 15:03:20 GMT 2023 , Edited by admin on Fri Dec 15 15:03:20 GMT 2023
PRIMARY
Related Record Type Details
Structure of NALIDIXATE SODIUM ANHYDROUS
ANHYDROUS->SOLVATE
Structure of NALIDIXIC ACID
PARENT -> SALT/SOLVATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966