The Nalidixic acid, with the CAS registry number 389-08-2, is also known as 1,4-Dihydro-1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carboxylic acid. It belongs to the product categories of Heterocyclic Compounds; Antibiotics for Research and Experimental Use; Biochemistry; Quinolones (Antibiotics for Research and Experimental Use); Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals. Its EINECS number is 206-864-7. This chemical's molecular formula is C₁₂H₁₂N₂O₃ and molecular weight is 232.24. What's more, its systematic name is 1-Ethyl-7-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid. Its classification codes are: (1)Anti-Infective Agents; (2)Antibacterial; (3)Drug / Therapeutic Agent; (4)Enzyme Inhibitors; (5)Human Data; (6)Mutation data; (7)Nucleic Acid Synthesis Inhibitors; (8)Reproductive Effect; (9)Tumor data. This chemical is a synthetic 1,8-naphthyridine antimicrobial agent with a limited bacteriocidal spectrum. It is an inhibitor of the subunit of bacterial DNA gyrase. It is also a tool in studies as a regulation of bacterial division. This chemical should be sealed and stored at the temperature of 0 - 6 °C. Moreover, it should be protected from light and air.

Physical properties of Nalidixic acid are: (1)ACD/LogP: 0.025; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.58; (4)ACD/LogD (pH 7.4): -1.54; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 6.12; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 70.5 Å²; (13)Index of Refraction: 1.605; (14)Molar Refractivity: 60.074 cm³; (15)Molar Volume: 174.429 cm³; (16)Polarizability: 23.815×10^-24cm³; (17)Surface Tension: 59.33 dyne/cm; (18)Density: 1.331 g/cm³; (19)Flash Point: 203.636 °C; (20)Enthalpy of Vaporization: 70.203 kJ/mol; (21)Boiling Point: 413.1 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 2-amino-5-methyl-pyridine which is derived from 2-methylpyridine, and then combines with ethyl orthoformate and diethyl malonate to get N-(2-methyl-5-amino pyridine). After cyclization at 260-270°C, hydrolyzation in sodium hydroxide to get 7-methyl-1,8-nalidixic 4-hydroxy-3-hydroxy acid. Finally, use bromoethane to do N-alkylation reaction and the product is isomerized to Nalidixic acid.

Uses of Nalidixic acid: it can be used to produce 1-ethyl-3-iodo-7-methyl-1H-[1,8]naphthyridin-4-one by heating. It will need reagents I₂, lead tetraacetate and solvent CCl₄ with the reaction time of 30 min. The yield is about 61.9%.

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It has a limited evidence of a carcinogenic effect and may cause sensitisation by inhalation and skin contact. This substance has a possible risk of harm to the unborn child. You should not breathe dust. When using it, you must avoid contact with eyes. When using it, you need wear suitable protective gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C\2c1c(nc(cc1)C)N(/C=C/2C(=O)O)CC
(2)Std. 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)
(3)Std. InChIKey: MHWLWQUZZRMNGJ-UHFFFAOYSA-N

The toxicity data is as follows: