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
- Molecular Weight:
- 232.24
- MOL File:
- 389-08-2.mol
- Modify Date:
- 2024/6/25 20:17:06
| 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 |
| form | Powder |
| pka | pKa 6.11± 0.02(Approximate) |
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
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|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302-H351 | |||||||||
| Precautionary statements | P202-P264-P270-P280-P301+P312-P308+P313 | |||||||||
| 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 | |||||||||
| Toxicity | LD50 in mice (mg/kg): 3300 orally; 500 s.c.; 176 i.v. (Lesher, 1962) | |||||||||
| NFPA 704 |
|
Nalidixic acid price More Price(9)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | N8878 | Nalidixic acid ≥98% | 389-08-2 | 5G | ₹2340 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | N8878 | Nalidixic acid ≥98% | 389-08-2 | 25G | ₹8730 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | N8878 | Nalidixic acid ≥98% | 389-08-2 | 100G | ₹18803.03 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 97023 | Nalidixic acid analytical standard | 389-08-2 | 100MG | ₹5780.55 | 2022-06-14 | Buy |
| TCI Chemicals (India) | N0490 | Nalidixic Acid | 389-08-2 | 25G | ₹4400 | 2022-05-26 | Buy |
Nalidixic acid Chemical Properties,Uses,Production
Chemical Properties
Crystalline Powder
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
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.
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.
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
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chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| WARUKSHA LABORATORIES PVT LTD | +91-7485988764 +91-7485988764 | Gujarat, India | 77 | 58 | Inquiry |
| Ions Pharma | +912266707500 | Maharashtra, India | 89 | 58 | Inquiry |
| Elixir Pharma | +91-9712378624 +91-9558826007 | Gujarat, India | 22 | 58 | Inquiry |
| Ishita Drugs And Industries Ltd | +91-7226995614 +91-7226995613 | Telangana, India | 47 | 58 | Inquiry |
| S D Fine Chem Limited | +91-9323715856 +91-9323715856 | Maharashtra, India | 368 | 58 | Inquiry |
| Unimark Remedies Ltd | +91-2267304120 +91-2267304120 | Maharashtra, India | 48 | 58 | Inquiry |
| Remedy Labs | 08048984743 | Ahmedabad, India | 78 | 58 | Inquiry |
| Gradient Exports | 91-22-66103373 | Maharashtra, India | 77 | 58 | Inquiry |
| Unimark Remedies Ltd. | 91-22-67304120 | Maharashtra, India | 26 | 58 | Inquiry |
| Tradeimpex International | 91-22-22010843 | Maharashtra, India | 64 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| WARUKSHA LABORATORIES PVT LTD | 58 |
| Ions Pharma | 58 |
| Elixir Pharma | 58 |
| Ishita Drugs And Industries Ltd | 58 |
| S D Fine Chem Limited | 58 |
| Unimark Remedies Ltd | 58 |
| Remedy Labs | 58 |
| Gradient Exports | 58 |
| Unimark Remedies Ltd. | 58 |
| Tradeimpex International | 58 |
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- Mar 11，2022
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