Nalidixic acid

Base Information

• Chemical Name: Nalidixic acid
• CAS No.: 389-08-2
• Molecular Formula: C12H12N2O3
• Molecular Weight: 232.239
• Hs Code.: 29339190
• European Community (EC) Number: 206-864-7
• NSC Number: 757432,82174
• UN Number: 3249
• UNII: 3B91HWA56M
• DSSTox Substance ID: DTXSID3020912
• Nikkaji Number: J2.039G
• Wikipedia: Nalidixic_acid
• Wikidata: Q281082
• NCI Thesaurus Code: C47630
• Metabolomics Workbench ID: 43074
• ChEMBL ID: CHEMBL5
• Mol file: 389-08-2.mol

Synonyms:1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylicacid;1-Ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid;1-Ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid;3-Carboxy-1-ethyl-7-methyl-1,8-naphthyridin-4-one;1,8-Naphthyridine-3-carboxylicacid, 1-ethyl-1,4-dihydro-7-methyl-4-oxo-;Dixiben;Eucistin;Innoxalomn;Nalidicron;Nalidixan;Nalidixin;Nalitucsan;Nalurin;Nelidix;Nevigramon;Poleon;Specifin;Urisal;Uroman;Wintomylon;

Chemical Property of Nalidixic acid

Chemical Property:

• Appearance/Colour: crystalline powder
• Vapor Pressure: 1.45E-07mmHg at 25°C
• Melting Point: 227-229 °C(lit.)
• Refractive Index: 1.6660 (estimate)
• Boiling Point: 413.1 °C at 760 mmHg
• PKA: pKa 6.11± 0.02(Approximate)
• Flash Point: 203.636 °C
• PSA: 72.19000
• Density: 1.331 g/cm³
• LogP: 1.42300
• Storage Temp.: 0-6°C
• Solubility.: chloroform: 20 mg/mL, clear
• Water Solubility.: 0.1 G/L (23 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 232.08479225
• Heavy Atom Count: 17
• Complexity: 378
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Nalidixic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-42/43-40-20/21/22-22
• Safety Statements: 22-36/37-45-24-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN1C=C(C(=O)C2=C1N=C(C=C2)C)C(=O)O
• 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 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.
• Therapeutic Function: Antibacterial
• 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.
• 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

Technology Process of Nalidixic acid

There total 20 articles about Nalidixic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

ethyl 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (33331-59-8) → nalidixic Acid (389-08-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 8h; Heating;

DOI:10.1055/s-2005-870019

Reference yield: 86.0%

→ nalidixic Acid (389-08-2)

Guidance literature:

Reference yield:

C16H19N3O5 (934343-42-7) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + methyl N-methylcarbamate (6642-30-4) + nalidixic Acid (389-08-2)

Guidance literature:

With aq. buffer; In acetonitrile; at 39 ℃; pH=7.1; Kinetics;

DOI:10.1016/j.bmcl.2006.11.074

upstream raw materials:

[(1-Ethyl-7-methyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carbonyl)-amino]-acetic acid ethyl ester

ethyl 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

2-Amino-6-methylpyridine

diethyl 2-{[(6-methyl-2-pyridyl)amino]methylene}propane-1,3-dioate

Downstream raw materials:

1-ethyl-7-methyl-1,8-naphthyridin-4(1H)-one

Ethyl 4-N-(1-Ethyl-1,4-Dihydro-7-Methyl-4-Oxo-1,8-Naphthyridine-3-Carbonyl)Aminomethylcyclohexanecarboxylate

C₁₉H₁₇N₅O₄

N'-(4-hydroxybenzylidene)-1-ethyl-1,4-dihydro-7-methyl-4-oxo-1,8-naphthyridine-3-carbohydrazide

Refernces

• 1、 Santilli et al.. "-". . p. 1038,1039. Retrieved 1975.
• 2、 Singh, Ram,Geetanjali. "Synthesis of selected novel covalently linked flavoquinolones". . p. 2315 - 2320. Retrieved 2007/10/03.