389-08-2
Nalidixic acid
CAS: 389-08-2
Molecular Formula: C12H12N2O3
389-08-2 - Names and Identifiers
| Name | Nalidixic acid |
| Synonyms | uroman uroneg uropan Win18,320 Wintomylon Nalidixicacid Nalidixic acid Nalidixic acid BP93.CH.P.95 Cetrimide Nalidixic acid Agar Supplement Nalidixic acid, Antibiotic for Culture Media Use Only 1-ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate 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 Nalidixic acid, 1,4-Dihydro-1-ethyl-7-methyl-1,8-naphthyridin-4-one-3-carboxylic acid |
| CAS | 389-08-2 |
| EINECS | 206-864-7 |
| InChI | InChI=1/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)/p-1 |
389-08-2 - Physico-chemical Properties
| Molecular Formula | C12H12N2O3 |
| Molar Mass | 232.24 |
| Density | 1.2243 (rough estimate) |
| Melting Point | 227-229 °C (lit.) |
| Boling Point | 374.4°C (rough estimate) |
| Flash Point | 203.6°C |
| Water Solubility | 0.1 G/L (23 ºC) |
| Solubility | Soluble in chloroform, slightly soluble in alcohol, strong lye, almost insoluble in water and ether |
| Vapor Presure | 1.45E-07mmHg at 25°C |
| Appearance | White to off-white powder |
| Color | White to light yellow |
| Merck | 14,6359 |
| BRN | 750515 |
| pKa | pKa 6.11± 0.02(Approximate) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | Sensitive to light and air |
| Refractive Index | 1.6660 (estimate) |
| MDL | MFCD00006884 |
| Physical and Chemical Properties | This product is light yellow crystalline powder. |
| Use | Anti-infective agents, E. Coli, Proteus and other bacilli have a certain antibacterial effect |
389-08-2 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R63 - Possible risk of harm to the unborn child R42/43 - May cause sensitization by inhalation and skin contact. R40 - Limited evidence of a carcinogenic effect R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R22 - Harmful if swallowed |
| Safety Description | S22 - Do not breathe dust. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S24 - Avoid contact with skin. S36 - Wear suitable protective clothing. |
| WGK Germany | 2 |
| RTECS | QN2885000 |
| FLUKA BRAND F CODES | 8-10-23 |
| HS Code | 29339190 |
| Toxicity | LD50 in mice (mg/kg): 3300 orally; 500 s.c.; 176 i.v. (Lesher, 1962) |
389-08-2 - Reference
| Reference Show more | 1. Wang Xiaodan, Luo Xiaoye, Qiu Shuyi. Isolation, screening and characterization of a strain of thermophilic actinomycete from taoku in Moutai [J]. China Brewing, 2018, 37(004):51-56. 2. Zhang Zheng, Ma gengqin, Wang Hongxuan, Hou Wenfu, Zhou Min. Biological characteristics and multi-drug efflux pump expression of drug-resistant Vibrio parahaemolyticus [J]. Modern food science and technology, 2020,36(08):15-22. |
389-08-2 - Introduction
Bacterial DNA synthetase and inhibitors of avian myeloblastoma virus reverse transcriptase.
Last Update：2022-10-16 17:25:02
389-08-2 - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| introduction | nalidixic acid, also known as nalidixic acid or tinman dragon, white to light yellow crystalline powder, odorless and tasteless. Melting point 229~230 ℃, insoluble in chloroform, alcohol, water, ether, is an antibacterial agent, used to treat urinary tract infections caused by gram-negative bacteria, and is the first generation of quinolones Representative of antibacterial drugs. |
| Mechanism of action | The mechanism of action of nalidixic acid is to inhibit the DNA gyrase of bacteria and interfere with the synthesis of DNA, thereby inhibiting the reproduction of bacteria in the growing period. The antibacterial spectrum is narrow and effective against most G-bacilli, but ineffective against Pseudomonas aeruginosa (Pseudomonas aeruginosa). It is ineffective against G bacteria and anaerobic bacteria. |
| biological activity | Nalidixic acid (NSC-82174) is a synthetic 1,8-diazaphthalene antibacterial agent with limited antibacterial spectrum and inhibition of bacterial DNA The A subunit of gyrogenase. |
| Target | Value |
| uses | anti-infective drugs have certain antibacterial effects on bacteria such as Escherichia coli and Proteus this product is an antibacterial agent, which can inhibit the synthesis of bacterial DNA and RNA and is used to treat urinary tract infections caused by gram-negative bacteria. Nalidixic acid is the representative of the first generation of quinolones, and the second generation is represented by pirazepam. The representative of the third generation quinolone antibacterial drugs is norfloxacin. inhibitors of bacterial DNA synthase (DNA gyrase) and avian myeloblastoma virus reverse transcriptase (avian myeloblastoma virus reverse transcriptase). |
| Production method | 2-amino-5-methylpyridine is prepared from 2-methylpyridine, and then it is condensed with ethyl orthoformate and diethyl malonate to synthesize N-(2-methyl-5-aminopyridine) methylmalonate diethyl ester, and then it is cyclized at 260-270 ℃ and then added to sodium hydroxide dilute solution for hydrolysis to obtain 7-Methyl -1, 8-Naphthalene-4-hydroxy-3-hydroxyacid. Finally, N-alkylation with bromoethane and heteroformation of nalidixic acid. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:32:06
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View History
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