Norfloxacin

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Norfloxacin
Category Antibiotics
Catalog number BBF-04625
CAS 70458-96-7
Molecular Weight 319.33
Molecular Formula C16H18FN3O3
Purity >98%

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Description

Norfloxacin is a broad-spectrum antibiotic that is active against both Gram-positive and Gram-negative bacteria, which functions by inhibiting DNA gyrase. It is a synthetic chemotherapeutic antibacterial agent occasionally used to treat common as well as complicated urinary tract infections. It is approved for use in children older than one year of age. However, it is associated with a number of rare serious adverse reactions as well as spontaneous tendon ruptures and irreversible peripheral neuropathy.

Specification

Related CAS 68077-27-0 (hydrochloride)
Synonyms Noroxin; Chibroxin; AM-715; MK-366; AM 715; MK 366; AM715; MK366; 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic Acid; Baccidal; Barazan; Chibroxine; N-Desmethylpefloxacin; Sebercim; Zoroxin
Storage Store at -20°C under inert atmosphere
IUPAC Name 1-ethyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
Canonical SMILES CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCNCC3)F)C(=O)O
InChI InChI=1S/C16H18FN3O3/c1-2-19-9-11(16(22)23)15(21)10-7-12(17)14(8-13(10)19)20-5-3-18-4-6-20/h7-9,18H,2-6H2,1H3,(H,22,23)
InChI Key OGJPXUAPXNRGGI-UHFFFAOYSA-N
Source Synthetic

Properties

Appearance Pale Yellow Solid
Application Anti-bacterial agents; enzyme inhibitors; nucleic acid synthesis inhibitors
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 555.8±50.0°C (Predicted)
Melting Point 220-221°C
Density 1.344 g/cm3
Solubility Soluble in Acetone, Chloroform; Freely soluble in Water; Slightly soluble in DMSO, Methanol (Heated)

Reference Reading

1.Degradation of quinolone antibiotic, norfloxacin, in aqueous solution using gamma-ray irradiation.
Sayed M1,2, Khan JA3, Shah LA3, Shah NS3,4, Khan HM5, Rehman F3, Khan AR6, Khan AM6. Environ Sci Pollut Res Int. 2016 Mar 28. [Epub ahead of print]
This study reports the efficiency of gamma-ray irradiation to degrade quinolone antibiotic, norfloxacin, in aqueous solution. Laboratory batch experiments were conducted to determine the "pseudo-first" order degradation kinetics of norfloxacin in the concentration ranges of 3.4-16.1 mg L-1 by gamma-ray irradiation. The dose constant was found to be dependent on the initial concentration of norfloxacin and gamma-ray irradiation dose rate (D r). The saturation of norfloxacin sample solutions with N2, air or N2O, and the presence of tert-butanol and 2-propanol showed that •OH played more crucial role in the degradation of norfloxacin. The second order rate constants of •OH, eaq -, and •H with norfloxacin were calculated to be 8.81 × 109, 9.54 × 108, and 1.10 × 109 M-1 s-1, respectively. The effects of various additives including CO3 2-, HCO3 -, NO3 -, NO2 -, and thiourea and the pH of the medium on the degradation of norfloxacin were also investigated.
2.Tannic Acid as a Potential Modulator of Norfloxacin Resistance in Staphylococcus Aureus Overexpressing norA.
Diniz-Silva HT, Cirino IC, Falcão-Silva Vdos S, Magnani M, de Souza EL, Siqueira-Júnior JP. Chemotherapy. 2016;61(6):319-22. doi: 10.1159/000443495. Epub 2016 May 3.
BACKGROUND: Tannins have shown inhibitory effects against pathogenic bacteria, and these properties make tannins potential modifying agents in bacterial resistance.

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