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Details

Stereochemistry ACHIRAL
Molecular Formula C12H11N2O3.Na
Molecular Weight 254.2171
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NALIDIXATE SODIUM ANHYDROUS

SMILES

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

InChI

InChIKey=ROKRAUFZFDQWLE-UHFFFAOYSA-M
InChI=1S/C12H12N2O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C12H11N2O3
Molecular Weight 231.2273
Charge -1
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 TargetPharmacologyConditionPotency
110.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NEGGRAM

Cmax

ValueDoseCo-administeredAnalytePopulation
27.8 μg/mL
1 g single, oral
NALIDIXIC ACID plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
327.7 μg × h/mL
1 g single, oral
NALIDIXIC ACID plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.5 h
1 g single, oral
NALIDIXIC ACID plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​

Drug as victim

PubMed

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
Y7NU182221
Record Status Validated (UNII)
Record Version