NALIDIXIC ACID

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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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	Inhibitor 8,504		110.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207	Curative		Approved 8,583	NEGGRAM

C_max

Value	Dose	Co-administered	Analyte	Population
27.8 μg/mL	1 g single, oral		NALIDIXIC ACID plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
327.7 μg × h/mL	1 g single, oral		NALIDIXIC ACID plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.5 h	1 g single, oral		NALIDIXIC ACID plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
28 g single, oral Overdose	healthy, 19 years	Disc. AE: Metabolic acidosis, Coma...
150 mg/kg single, oral Overdose	unhealthy, 6 months	Disc. AE: Vomiting, Intracranial hypertension...
1 g 4 times / day steady, oral Recommended	unhealthy, adult	Other AEs: Phototoxicity...

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AEs

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AE	Significance	Dose	Population
Coma	1 patient Disc. AE	28 g single, oral Overdose	healthy, 19 years
Metabolic acidosis	1 patient Disc. AE	28 g single, oral Overdose	healthy, 19 years
Intracranial hypertension	12 patients Disc. AE	150 mg/kg single, oral Overdose	unhealthy, 6 months
Vomiting	12 patients Disc. AE	150 mg/kg single, oral Overdose	unhealthy, 6 months
Convulsions	2 patients Disc. AE	150 mg/kg single, oral Overdose	unhealthy, 6 months

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 OAT1 725 OAT3 747 MRP4 290 UGT1A8 37 UGT1A10 37	OAT1 395 UGT 219

Drug as perpetrator

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Target	Modality	Activity
UGT1A10 46	inhibitor 4,027	inconclusive
UGT1A8 49	inhibitor 4,027	inconclusive
OAT3 749	inhibitor 4,027	yes [IC50 0.3 uM]
MRP4 345	inhibitor 4,027	yes [IC50 4.2 uM]
OAT1 730	inhibitor 4,027	yes [IC50 78.3 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
OAT1 395	substrate 4,014	likely
UGT 219	substrate 4,014	yes

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Large-scale preparation of recombinant ovine prolactin and determination of its in vitro and in vivo activity.	2001 Aug	11483014
Susceptibility of Arcobacter butzleri isolates to 23 antimicrobial agents.	2001 Dec	11737626
Quinolones and false-positive urine screening for opiates by immunoassay technology.	2001 Dec 26	11754677
Evaluation of a selective broth for detection of Staphylococcus aureus using impedance microbiology.	2001 Jan	11198440
Etiologies of the urinary tract infections in a Yemeni City.	2001 Jul	11479641

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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
Record UNII	3B91HWA56M
Record Status	`Validated (UNII)`
Record Version

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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

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Classification Tree

Code System

Code

Antibacterial

LIVERTOX

663

Other quinolones

WHO-ATC

J01MB02

Antibiotic

NCI_THESAURUS

C795

Other quinolones

WHO-VATC

QJ01MB02

Anti-Infective Agent

NCI_THESAURUS

C255

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Code System

Code

Type

Description

RXCUI

7240

PRIMARY

SMS_ID

100000092361

PRIMARY

INN

1450

PRIMARY

MERCK INDEX

m7714

PRIMARY

Merck Index

FDA UNII

3B91HWA56M

PRIMARY

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Related Record

Type

Details


					J17QL41ZAG

NALIDIXATE SODIUM

SALT/SOLVATE -> PARENT


					06F1BL6L7G

MEGLUMINE NALIDIXIC ACID

SALT/SOLVATE -> PARENT

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Related Record

Type

Details


					NZJ3R8S4EH

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

METABOLITE -> PARENT

Comments:

Metabolite to parent drug ratio in non-uraemic human plasma.

Interaction Type:

METABOLITE TO PARENT DRUG RATIO

Qualification:

PLASMA; URINE

Amount:

RELATIONSHIP_AMOUNT [0.15 to 0.2] METABOLITE/PARENT RATIO (limits)

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Related Record

Type

Details


					3B91HWA56M

NALIDIXIC ACID

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator