NALIDIXIC ACID

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H12N2O3
Molecular Weight	232.2353
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C=C(C(O)=O)C(=O)C2=C1N=C(C)C=C2

InChI

InChIKey=MHWLWQUZZRMNGJ-UHFFFAOYSA-N

InChI=1S/C12H12N2O3/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)

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/017430s032lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC432036/pdf/pnas00033-0067.pdf	Inhibitor 8504		110.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/017430s032lbl.pdf	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

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 OAT1 725 OAT3 747 MRP4 290 UGT1A8 37 UGT1A10 37	OAT1 395 UGT 219

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
UGT1A10 46	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/43/6/812.full.pdf?with-ds=yes	inconclusive
UGT1A8 49	inhibitor 4027 Sources: https://dmd.aspetjournals.org/content/dmd/43/6/812.full.pdf?with-ds=yes	inconclusive
OAT3 749	inhibitor 4027 Sources: https://jpet.aspetjournals.org/content/362/3/450#T2	yes [IC50 0.3 uM]
MRP4 345	inhibitor 4027 Sources: https://jpet.aspetjournals.org/content/362/3/450#T2	yes [IC50 4.2 uM]
OAT1 730	inhibitor 4027 Sources: https://jpet.aspetjournals.org/content/362/3/450#T2	yes [IC50 78.3 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC188773/pdf/aac00039-0070.pdf#page=1 Page: 1,6	yes [Inhibition 500 uM]	no (co-administration study) Comment: no effects on theophylline pharmacokinetics were reported Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC188773/pdf/aac00039-0070.pdf#page=1 Page: 1,6

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 395	substrate 4014 Sources: https://jpet.aspetjournals.org/content/362/3/450	likely
UGT 219	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/3205675/	yes

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Antimicrobial susceptibility patterns of Campylobacter jejuni strains isolated from hospitalized children in Athens, Greece.	2002-05	12003974
Increasing quinolone resistance in Salmonella enterica serotype Enteritidis.	2002-05	11996688
Excess mortality associated with antimicrobial drug-resistant Salmonella typhimurium.	2002-05	11996684
Trends in fluoroquinolone (ciprofloxacin) resistance in enterobacteriaceae from bacteremias, England and Wales, 1990-1999.	2002-05	11996681
On the effect of covalently appended quinolones on termini of DNA duplexes.	2002-04-24	11960452
Serovars of Salmonella isolated from Danish turkeys between 1995 and 2000 and their antimicrobial resistance.	2002-04-13	11995678
Incidence and molecular analysis of Vibrio cholerae associated with cholera outbreak subsequent to the super cyclone in Orissa, India.	2002-04	12002529
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.	2002-04	11971772
Effect of an efflux pump inhibitor on the MIC of nalidixic acid for Acinetobacter baumannii and Stenotrophomonas maltophilia clinical isolates.	2002-04	11909848
Identification of an immunodominant drug efflux pump in Burkholderia cepacia.	2002-04	11909835
Comparison of aqueous commercial cleaners for effectiveness in removing Escherichia coli O157:H7 and Salmonella muenchen from the surface of apples.	2002-03-25	11929170
[Studies on halophilic vibrios causing a food poisoning outbreak in the city of Vladivostok].	2002-03-08	11881491
Comparison of aztreonam against other antibiotics used in urinary tract infections.	2002-03-05	11873424
Febrile urinary tract infection: Escherichia coli susceptibility to oral antimicrobials.	2002-03	11956854
Emergence and rapid spread of tetracycline-resistant Vibrio cholerae strains, Madagascar.	2002-03	11927038
Inactivation of Escherichia coli O157:H7 on inoculated alfalfa seeds with ozonated water and heat treatment.	2002-03	11899041
Resistance of Klebsiella pneumoniae strains producing and not producing ESBL (extended-spectrum beta-lactamase) type enzymes to selected non-beta-lactam antibiotics.	2002-03	11889457
Activity of clinafloxacin, compared with six other quinolones, against Acinetobacter baumannii clinical isolates.	2002-03	11864947
Screening of antibiotic resistant inhibitors from local plant materials against two different strains of Staphylococcus aureus.	2002-03	11849842
Modified Pseudomonas agar: new differential medium for the detection/enumeration of Pseudomonas aeruginosa in mineral water.	2002-03	11777584
Time-dependent toxicity in the long-term inhibition assay with Vibrio fischeri.	2002-02	11999781
Comparative antibiotic resistance of diarrheal pathogens from Vietnam and Thailand, 1996-1999.	2002-02	11897070
[Evolution of susceptibility of aerobic gram-negative aerobic bacilli to quinolones and fluoroquinolones in a university hospital (1992-2000)].	2002-02	11873626
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.	2002-02	11858908
Green fluorescent protein-based biosensor for detecting SOS-inducing activity of genotoxic compounds.	2002-01	11733081
In vitro antibiotic susceptibility of bacteria isolated from EUS-affected fishes in India.	2002	11967051
Quinolones and false-positive urine screening for opiates by immunoassay technology.	2001-12-26	11754677
Reduced fluoroquinolone susceptibility in Salmonella enterica serotypes in travelers returning from Southeast Asia.	2001-12-19	11747728
Campylobacter, Salmonella, Shigella and Escherichia coli in live and dressed poultry from metropolitan accra.	2001-12-04	11764888
Synthesis, characterization and antitumor activity of quinolone-platinum(II) conjugates.	2001-12-01	11730897
Typhoid and paratyphoid fever: a 10-year retrospective study of 41 cases in a Parisian hospital.	2001-12-01	11726293
[Activity of new fluoroquinolones against clinical isolates of Acinetobacter baumannii].	2001-12	11856982
Susceptibility of Arcobacter butzleri isolates to 23 antimicrobial agents.	2001-12	11737626
[Increasing incidence and the mechanism of resistance of nalidixic acid resistant Shigella sonnei].	2001-11	11766375
Induction of pCW3-encoded tetracycline resistance in Clostridium perfringens involves a host-encoded factor.	2001-11	11735372
Susceptibility patterns of enteroaggregative Escherichia coli associated with traveller's diarrhoea: emergence of quinolone resistance.	2001-11	11699598
Tropical diarrhoea: new developments in traveller's diarrhoea.	2001-10	11964874
Epidemiological analysis of Salmonella enteritidis isolates in Singapore.	2001-10	11798253
Comparison of minimum inhibitory concentration values for fluoroquinolones against Escherichia coli causing urinary tract infection in both hospitalized patients and outpatients.	2001-10	11744939
Bacterial aetiology and anti-microbial resistance of childhood diarrhoea in Yemen.	2001-10	11695731
[Comparative study of the bacteriostatic and bactericidal activity of levofloxacin against Pasteurella strains isolated from man].	2001-10	11692747
Antibiotic resistance in Escherichia coli isolates obtained from animals, foods and humans in Spain.	2001-10	11691568
Trends in quinolone susceptibility of Enterobacteriaceae among inpatients of a large university hospital: 1992-98.	2001-10	11683796
[The current antimicrobial resistance situation in Swiss veterinary medicine].	2001-10	11680911
Fluoroquinolone adverse effects and drug interactions.	2001-10	11642691
Epidemiology of shigellosis in Lagos, Nigeria: trends in antimicrobial resistance.	2001-09	11761772
Antibiotic resistance and sero-groups of shigella among paediatric out-patients in southwest Ethiopia.	2001-06	12002106
Enterococcal urinary tract infections: eight years experience at a regional hospital in Trinidad, West Indies.	2001-01	11779446
Single or double mutational alterations of gyrA associated with fluoroquinolone resistance in Campylobacter jejuni and Campylobacter coli.	2001	11759087
[Multidrug resistance to antibacterial drugs of Salmonella enterica subsp. enterica strains isolated in Poland in the 1998-1999 period].	2001	11757401

Patents

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 `Wed Apr 02 07:48:09 GMT 2025` Edited by `admin` on `Wed Apr 02 07:48:09 GMT 2025`
Record UNII	3B91HWA56M
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NALIDIXIC ACID

Official Name

English

NEGGRAM

Preferred Name

English

WIN-18320

Code

English

1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID, 1-ETHYL-1,4-DIHYDRO-7-METHYL-4-OXO-

Common Name

English

NALIDIXIC ACID [VANDF]

Common Name

English

NALIDIXIC ACID [MI]

Common Name

English

NSC-82174

Code

English

NALIDIXIC ACID [JAN]

Common Name

English

NALIDIXIC ACID [HSDB]

Common Name

English

NALIDIXIC ACID [ORANGE BOOK]

Common Name

English

NALIDIXIC ACID [EP IMPURITY]

Common Name

English

WIN 18,320

Code

English

1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid

Systematic Name

English

NALIDIXATE

Common Name

English

nalidixic acid [INN]

Common Name

English

NALIDIXIC ACID [MART.]

Common Name

English

NALIDIXIC ACID [USAN]

Common Name

English

Nalidixic acid [WHO-DD]

Common Name

English

NALIDIXIC ACID [USP IMPURITY]

Common Name

English

Classification Tree Code System Code

LIVERTOX

663