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Nalidixic acid

Product Name
Nalidixic acid
CAS No.
389-08-2
Chemical Name
Nalidixic acid
Synonyms
neggram;Nalidixic acid BP93.CH.P.95;1,4-DIHYDRO-1-ETHYL-7-METHYL-4-OXO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACID;cybis;nalix;NOGRAM;uropan;uroneg;uroman;negram
CBNumber
CB1194283
Molecular Formula
C12H12N2O3
Formula Weight
232.24
MOL File
389-08-2.mol
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Nalidixic acid Property

Melting point:
227-229 °C (lit.)
Boiling point:
374.4°C (rough estimate)
Density 
1.2243 (rough estimate)
refractive index 
1.6660 (estimate)
storage temp. 
2-8°C
solubility 
chloroform: 20 mg/mL, clear
pka
pKa 6.11± 0.02(Approximate)
form 
Powder
color 
White to light yellow
Water Solubility 
0.1 G/L (23 ºC)
Merck 
14,6359
BRN 
750515
Stability:
Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference
389-08-2(CAS DataBase Reference)
EPA Substance Registry System
Nalidixic acid (389-08-2)
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Safety

Hazard Codes 
Xn
Risk Statements 
63-42/43-40-20/21/22-22
Safety Statements 
22-36/37-45-24-36
WGK Germany 
2
RTECS 
QN2885000
F 
8-10-23
HS Code 
29339190
Hazardous Substances Data
389-08-2(Hazardous Substances Data)
Toxicity
LD50 in mice (mg/kg): 3300 orally; 500 s.c.; 176 i.v. (Lesher, 1962)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H351Suspected of causing cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
97023
Product name
Nalidixic acid
Purity
analytical standard
Packaging
100mg
Price
$72.6
Updated
2024/03/01
TCI Chemical
Product number
N0490
Product name
Nalidixic Acid
Purity
>95.0%(T)
Packaging
25g
Price
$63
Updated
2024/03/01
Alfa Aesar
Product number
B25096
Product name
Nalidixic acid, 99%
Packaging
5g
Price
$30.6
Updated
2024/03/01
Alfa Aesar
Product number
B25096
Product name
Nalidixic acid, 99%
Packaging
25g
Price
$98.5
Updated
2024/03/01
Cayman Chemical
Product number
19807
Product name
Nalidixic Acid
Purity
≥98%
Packaging
10g
Price
$32
Updated
2024/03/01
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Nalidixic acid Chemical Properties,Usage,Production

Chemical Properties

Crystalline Powder

Originator

Neggram,Winthrop,US,1964

Uses

Quinolone antibacterial.

Uses

Nalidixic acid(NegGram) is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the A subunit of bacterial DNA gyrase. Evidence exists that the active metabolite, hydroxynalidixic acid, binds stron

Uses

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.

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.

Manufacturing Process

A warm solution containing 41 grams of 4-hydroxy-7-methyl-1,8- naphthyridine-3-carboxylic acid and 39 grams of potassium hydroxide in 1 liter of ethanol and 200 cc of water was treated with 50 cc of ethyl iodide and the resulting mixture was refluxed gently overnight, acidified with hydrochloric acid and cooled. The resulting precipitate was collected and recrystallized twice from acetonitrile to yield 26 grams (56% yield) of 1-ethyl-7-methyl-4- oxo-1,8-naphthyridine-3-carboxylic acid, MP 229° to 230°C.
The starting material is prepared by reacting 2-amino-6-methylpyridine with ethoxymethylene-malonic acid diethyl ester and then reacting that product with sodium hydroxide.

brand name

Neggram(Sanofi Aventis).

Therapeutic Function

Antibacterial

Antimicrobial activity

It displays good activity in vitro against a wide range of Enterobacteriaceae.

General Description

Cream-colored powder.

Air & Water Reactions

Insoluble in water.

Health Hazard

SYMPTOMS: Ingestion of Nalidixic acid may cause nausea, vomiting, abdominal pain, allergic reactions and possible liver damage.

Fire Hazard

Flash point data for Nalidixic acid are not available, but Nalidixic acid is probably combustible.

Pharmaceutical Applications

A 1,8 naphthyridone derivative available for oral administration.

Pharmacokinetics

Oral absorption: >90%
Cmax 1 g oral: c. 25 mg/L
Plasma half-life:c.1.5h
Volume of distribution :0.4 L/kg
Plasma protein binding: 93%
The plasma concentrations achieved after oral administration vary widely. In infants with acute shigellosis, absorption is much impaired by diarrhea. Administration with an alkaline compound leads to higher plasma concentrations, partly as the result of enhanced solubility (nalidixic acid is much more soluble at higher pH) and absorption and partly because of reduced tubular reabsorption.
It is rapidly metabolized, principally to the hydroxy acid, which is bacteriologically active, and glucuronide conjugates, which are not. The entire administered dose appears in the urine over a 24 h period. Elimination is reduced by probenecid. In the presence of renal impairment there is little accumulation of the active compound because it continues to be metabolized. However, elimination of metabolites is progressively delayed as renal function declines. About 4% of a dose appears in the feces.

Clinical Use

1-Ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid (NegGram) occurs as a pale buff crystalline powder that is sparingly soluble in water and ether but solublein most polar organic solvents.Nalidixic acid is useful in the treatment of urinary tractinfections in which Gram-negative bacteria predominate.The activity against indole-positive Proteus spp. is particularlynoteworthy, and nalidixic acid and its congeners representimportant alternatives for the treatment of urinary tractinfections caused by strains of these bacteria resistant toother agents. Nalidixic acid is rapidly absorbed, extensivelymetabolized, and rapidly excreted after oral administration.The 7-hydroxymethyl metabolite is significantly more activethan the parent compound. Further metabolism of theactive metabolite to inactive glucuronide and 7-carboxylicacid metabolites also occurs. Nalidixic acid possesses at1/2elim of 6 to 7 hours. It is eliminated, in part, unchanged inthe urine and 80% as metabolites.

Side effects

Adverse reactions are generally those common to all quinolones: gastrointestinal tract and CNS disturbances and skin rashes, including eruptions related to photosensitivity. About half of the reported CNS reactions involve visual disturbances, hallucinations or disordered sensory perception. Severe excitatory states, including acute psychoses and convulsions, are usually observed in patients receiving high dosages. The drug should be avoided in patients with psychiatric disorders or epilepsy.
Acute intracranial hypertension has been observed in children, some of whom have also manifested cranial nerve palsies. Hemorrhage has occurred in patients who were also receiving warfarin, presumably due to displacement of the anticoagulant from its protein binding sites by the nalidixic acid. Hemolytic anemia has been described several times in infants with or without glucose-6-phosphate dehydrogenase deficiency; in adults, death has occurred from autoimmune hemolytic anemia. Arthralgia and severe metabolic acidosis have rarely been reported.

Safety Profile

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion and subcutaneous routes. An experimental teratogen. Human systemic effects: convulsions, hyperglycemia, sweating, and blood changes in children. Experimental reproductive effects.Questionable carcinogen with experimental carcinogenic and tumorigenic data. Human mutation data reported. Used as an antibacterial agent and urinary tract antiseptic. When heated to decomposition it emits toxic fumes of NOx.

Synthesis

Nalidixic acid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthiridin-3- carboxylic acid (33.2.4), is synthesized by the following scheme. In the first stage, the reaction of 2-amino-6-methylpyridine and diethyl ethoxymethylenemalonate forms the substituted product (33.2.1), which when heated cyclizes to ethyl ester of 4-hydroxy -7-methyl-1,8-napthiridin-3-carboxylic acid (33.2.2). Hydrolyzing the resulting product with a base gives the corresponding acid (33.2.3). Alkylating this with ethyl iodide in the presence of potassium hydroxide gives nalidixic acid.

Drug interactions

Potentially hazardous interactions with other drugs
Aminophylline and theophylline: possibly increased risk of convulsions.
Analgesics: increased risk of convulsions with NSAIDs.
Antibacterials: possibly antagonised by nitrofurantoin.
Anticoagulants: anticoagulant effect of coumarins enhanced.
Antimalarials: manufacturer of artemether with lumefantrine advises avoid.
Ciclosporin: increased risk of nephrotoxicity.
Cytotoxics: increases risk of melphalan toxicity

Metabolism

Nalidixic acid is partially metabolised in the liver to hydroxynalidixic acid, which has antibacterial activity similar to that of nalidixic acid and accounts for about 30% of active drug in the blood. Both nalidixic acid and hydroxynalidixic acid are rapidly metabolised to inactive glucuronide and dicarboxylic acid derivatives; the major inactive metabolite 7-carboxynalidixic acid is usually only detected in urine.

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. [Lesher et al. J Med & Pharm Chem 5 1063 1962.]

Nalidixic acid Preparation Products And Raw materials

Raw materials

Diethyl ester 2-Amino-5-methylpyridine 1,8-Naphthyridine Diethyl ethoxymethylenemalonate Triethyl orthoformate 5-Amino-2-methylpyridine Bromoethane Malonic acid

Preparation Products

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View Lastest Price from Nalidixic acid manufacturers

Hebei Yanxi Chemical Co., Ltd.
Product
Nalidixic acid 389-08-2
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20 tons
Release date
2023-10-07
Shaanxi Dideu Medichem Co. Ltd
Product
Nalidixic acid 389-08-2
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20t
Release date
2024-06-25
Zhuozhou Wenxi import and Export Co., Ltd
Product
Nalidixic acid 389-08-2
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-08-11

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  • NALIDIXIC ACID FREE ACID
  • NALIDIXIC ACID, USP
  • NALIDIXIC ACID HIGH PURITY GRADE 98+%
  • Nalidixic acid, 99.50%
  • NALIDIXICACID,CRYSTAL,REAGENT