Nalidixic acid

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For Research Use Only.

Category

Phenols

Cat.No.

NP4607

CAS

389-08-2

Product Name

Nalidixic acid

Structure

Product Details

Description

Nalidixic acid is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of bacterial DNA polymerase (DNA gyrase) and avian myeloblastoma virus reverse transcriptase.

Synonyms

NSC-82174; NSC82174; 1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic Acid; 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic Acid; Betaxina; Cybis; Dixiben; Eucistin; NegGram; Nelidix; Wintomylon

IUPAC Name

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

Molecular Weight

232.24

Molecular Formula

C12H12N2O3

Canonical SMILES

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

InChI

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)

InChIKey

MHWLWQUZZRMNGJ-UHFFFAOYSA-N

Boiling Point

413.1°C at 760 mmHg

Melting Point

225-231°C

Purity

>98%

Density

1.331 g/cm3

Solubility

Slightly soluble in Chloroform, DMSO (Heated)

Appearance

Pale Yellow Solid

Storage

Store at 2-8°C

BRN

750515

Chemical Properties

Crystalline Powder

Color

White to light yellow

Definition

ChEBI: A monocarboxylic acid comprising 1,8-naphthyridin-4-one substituted by carboxylic acid, ethyl and methyl groups at positions 3, 1, and 7, respectively.

EINECS

206-864-7

8-10-23

Form

Powder

Hazard Class

HS Code

29339190

pKa

pKa 6.11± 0.02(Approximate)

Purification Methods

Nalidixic acid crystallises from H2O or EtOH as a pale buff powder. It is soluble at 23o in CHCl3 (3.5%), toluene (0.16%), MeOH (0.13%), EtOH (0.09%), H2O (0.01%) and Et2O (0.01%). It inhibits nucleic acid and protein synthesis in yeast.

Refractive Index

1.6660 (estimate)

Risk Statements

63-42/43-40-20/21/22-22

RTECS

QN2885000

Safety Statements

22-36/37-45-24-36

Stability

Stable. Incompatible with strong oxidizing agents.

Toxicity

LD50 in mice (mg/kg): 3300 orally; 500 s.c.; 176 i.v. (Lesher, 1962)

Uses

Quinolone antibacterial.

Water Solubility

0.1 g/L (23 °C)

WGK Germany

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