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

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H12N2O3.C7H17NO5
Molecular Weight 427.4489
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEGLUMINE NALIDIXIC ACID

SMILES

CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCN1C=C(C(O)=O)C(=O)C2=CC=C(C)N=C12

InChI

InChIKey=JWZFGKNDDDVNBX-WZTVWXICSA-N
InChI=1S/C12H12N2O3.C7H17NO5/c1-3-14-6-9(12(16)17)10(15)8-5-4-7(2)13-11(8)14;1-8-2-4(10)6(12)7(13)5(11)3-9/h4-6H,3H2,1-2H3,(H,16,17);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1

HIDE SMILES / InChI
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
Molecular Formula C7H17NO5
Molecular Weight 195.2136
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

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
2588
Curator's Comment: Negligible amounts of nalidixic acid cross the blood brain barrier.

Originator

Approval Year

1964
103
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 110.0 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
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
Health Status: healthy
Age Group: 19 years
Sex: F
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
Health Status: unhealthy
Age Group: 6 months
Sex: unknown
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
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
Health Status: healthy
Age Group: 19 years
Sex: F
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
Health Status: healthy
Age Group: 19 years
Sex: F
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
Health Status: unhealthy
Age Group: 6 months
Sex: unknown
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
Health Status: unhealthy
Age Group: 6 months
Sex: unknown
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
Health Status: unhealthy
Age Group: 6 months
Sex: unknown
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
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/21879777/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

OAT1
725

OAT3
747

MRP4
290

UGT1A8
37

UGT1A10
37
OAT1
395

UGT
219
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
UGT1A10
46
 inconclusive
UGT1A8
49
 inconclusive
OAT3
749
 yes [IC50 0.3 uM]
MRP4
345
 yes [IC50 4.2 uM]
OAT1
730
 yes [IC50 78.3 uM]
CYP1A2
2333
 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
395
 likely
UGT
219
 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
eMolecules
529362
https://www.emolecules.com/cgi-bin/more?vid=529362
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
PubMed

PubMed

TitleDatePubMed
Antimicrobial susceptibility patterns of Campylobacter jejuni strains isolated from hospitalized children in Athens, Greece.
2002-05
Increasing quinolone resistance in Salmonella enterica serotype Enteritidis.
2002-05
Excess mortality associated with antimicrobial drug-resistant Salmonella typhimurium.
2002-05
Trends in fluoroquinolone (ciprofloxacin) resistance in enterobacteriaceae from bacteremias, England and Wales, 1990-1999.
2002-05
On the effect of covalently appended quinolones on termini of DNA duplexes.
2002-04-24
Serovars of Salmonella isolated from Danish turkeys between 1995 and 2000 and their antimicrobial resistance.
2002-04-13
Incidence and molecular analysis of Vibrio cholerae associated with cholera outbreak subsequent to the super cyclone in Orissa, India.
2002-04
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.
2002-04
Effect of an efflux pump inhibitor on the MIC of nalidixic acid for Acinetobacter baumannii and Stenotrophomonas maltophilia clinical isolates.
2002-04
Identification of an immunodominant drug efflux pump in Burkholderia cepacia.
2002-04
Comparison of aqueous commercial cleaners for effectiveness in removing Escherichia coli O157:H7 and Salmonella muenchen from the surface of apples.
2002-03-25
[Studies on halophilic vibrios causing a food poisoning outbreak in the city of Vladivostok].
2002-03-08
Comparison of aztreonam against other antibiotics used in urinary tract infections.
2002-03-05
Febrile urinary tract infection: Escherichia coli susceptibility to oral antimicrobials.
2002-03
Emergence and rapid spread of tetracycline-resistant Vibrio cholerae strains, Madagascar.
2002-03
Inactivation of Escherichia coli O157:H7 on inoculated alfalfa seeds with ozonated water and heat treatment.
2002-03
Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics.
2002-03
Activity of clinafloxacin, compared with six other quinolones, against Acinetobacter baumannii clinical isolates.
2002-03
Screening of antibiotic resistant inhibitors from local plant materials against two different strains of Staphylococcus aureus.
2002-03
Modified Pseudomonas agar: new differential medium for the detection/enumeration of Pseudomonas aeruginosa in mineral water.
2002-03
Time-dependent toxicity in the long-term inhibition assay with Vibrio fischeri.
2002-02
Comparative antibiotic resistance of diarrheal pathogens from Vietnam and Thailand, 1996-1999.
2002-02
[Evolution of susceptibility of aerobic gram-negative aerobic bacilli to quinolones and fluoroquinolones in a university hospital (1992-2000)].
2002-02
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.
2002-02
Green fluorescent protein-based biosensor for detecting SOS-inducing activity of genotoxic compounds.
2002-01
In vitro antibiotic susceptibility of bacteria isolated from EUS-affected fishes in India.
2002
Quinolones and false-positive urine screening for opiates by immunoassay technology.
2001-12-26
Reduced fluoroquinolone susceptibility in Salmonella enterica serotypes in travelers returning from Southeast Asia.
2001-12-19
Campylobacter, Salmonella, Shigella and Escherichia coli in live and dressed poultry from metropolitan accra.
2001-12-04
Synthesis, characterization and antitumor activity of quinolone-platinum(II) conjugates.
2001-12-01
Typhoid and paratyphoid fever: a 10-year retrospective study of 41 cases in a Parisian hospital.
2001-12-01
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].
2001-12
Susceptibility of Arcobacter butzleri isolates to 23 antimicrobial agents.
2001-12
[Increasing incidence and the mechanism of resistance of nalidixic acid resistant Shigella sonnei].
2001-11
Induction of pCW3-encoded tetracycline resistance in Clostridium perfringens involves a host-encoded factor.
2001-11
Susceptibility patterns of enteroaggregative Escherichia coli associated with traveller's diarrhoea: emergence of quinolone resistance.
2001-11
Tropical diarrhoea: new developments in traveller's diarrhoea.
2001-10
Epidemiological analysis of Salmonella enteritidis isolates in Singapore.
2001-10
Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients.
2001-10
Bacterial aetiology and anti-microbial resistance of childhood diarrhoea in Yemen.
2001-10
[Comparative study of the bacteriostatic and bactericidal activity of levofloxacin against Pasteurella strains isolated from man].
2001-10
Antibiotic resistance in Escherichia coli isolates obtained from animals, foods and humans in Spain.
2001-10
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.
2001-10
[The current antimicrobial resistance situation in Swiss veterinary medicine].
2001-10
Fluoroquinolone adverse effects and drug interactions.
2001-10
Epidemiology of shigellosis in Lagos, Nigeria: trends in antimicrobial resistance.
2001-09
Antibiotic resistance and sero-groups of shigella among paediatric out-patients in southwest Ethiopia.
2001-06
Enterococcal urinary tract infections: eight years experience at a regional hospital in Trinidad, West Indies.
2001-01
Single or double mutational alterations of gyrA associated with fluoroquinolone resistance in Campylobacter jejuni and Campylobacter coli.
2001
[Multidrug resistance to antibacterial drugs of Salmonella enterica subsp. enterica strains isolated in Poland in the 1998-1999 period].
2001
Patents

Patents

20010006677
50
JP2001500477A
122
JP2002541233A
406
JP2009541210A
80
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 Mon Mar 31 18:46:39 GMT 2025
Edited
by admin
on Mon Mar 31 18:46:39 GMT 2025
Record UNII
06F1BL6L7G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLGLUCAMINE SALT OF NALIDIXIC ACID
Preferred Name English
MEGLUMINE NALIDIXIC ACID
Common Name English
Code System Code Type Description
CAS
23277-59-0
Created by admin on Mon Mar 31 18:46:39 GMT 2025 , Edited by admin on Mon Mar 31 18:46:39 GMT 2025
PRIMARY
FDA UNII
06F1BL6L7G
Created by admin on Mon Mar 31 18:46:39 GMT 2025 , Edited by admin on Mon Mar 31 18:46:39 GMT 2025
PRIMARY
PUBCHEM
76972612
Created by admin on Mon Mar 31 18:46:39 GMT 2025 , Edited by admin on Mon Mar 31 18:46:39 GMT 2025
PRIMARY
Related Record Type Details
Structure of MEGLUMINE
PARENT -> SALT/SOLVATE
Structure of NALIDIXIC ACID
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of NALIDIXIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
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