Pefloxacin
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| Category | Antibiotics |
| Catalog number | BBF-03873 |
| CAS | 70458-92-3 |
| Molecular Weight | 333.36 |
| Molecular Formula | C17H20FN3O3 |
| Purity | >98% |
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Description
Pefloxacin is a synthetic broad-spectrum fluoroquinolone antibacterial agent active against most gram-negative and gram-positive bacteria. Pefloxacin inhibits the activity of microbial DNA gyrase and topoisomerase IV. This disrupts DNA replication and prevents cell division.
Specification
| Related CAS | 70458-95-6 (Mesylate) 149676-40-4 (mesylate dihydrate) |
| Synonyms | 1584RB; 1589 RB; EU 5306 EU-5306; Pefloxacinium |
| Storage | Store at 2-8°C |
| IUPAC Name | 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid |
| Canonical SMILES | CCN1C=C(C(=O)C2=CC(=C(C=C21)N3CCN(CC3)C)F)C(=O)O |
| InChI | InChI=1S/C17H20FN3O3/c1-3-20-10-12(17(23)24)16(22)11-8-13(18)15(9-14(11)20)21-6-4-19(2)5-7-21/h8-10H,3-7H2,1-2H3,(H,23,24) |
| InChI Key | FHFYDNQZQSQIAI-UHFFFAOYSA-N |
| Source | Synthetic |
Properties
| Appearance | Light Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 529.1°C at 760 mmHg |
| Density | 1.32 g/cm3 |
| Solubility | 0.1N NaOH (10mg/mL): Clear and very faint yellow solution |
Reference Reading
1.Fluoroquinolone Resistance in Salmonella and the Utility of Pefloxacin Disk Diffusion [corrected].
Fang FC1. J Clin Microbiol. 2015 Nov;53(11):3401-4. doi: 10.1128/JCM.02270-15. Epub 2015 Aug 26.
Fluoroquinolone resistance is a serious and increasingly common problem in Salmonella. Two companion studies in this issue of the Journal of Clinical Microbiology (E. Deak, R. Skov, J. A. Hindler, and R. M. Humphries, J Clin Microbiol 53:3405-3410, 2015, http://dx.doi.org/10.1128/JCM.01393-15; R. Skov, E. Matuschek, M. Sjölund-Karlsson, J. Åhman, A. Petersen, M. Stegger, M. Torpdahl, and G. Kahlmeter, J Clin Microbiol 53:3411-3417, 2015, http://dx.doi.org/10.1128/JCM.01287-15) provide data to support the use of pefloxacin disk diffusion as a convenient and inexpensive surrogate laboratory method to detect fluoroquinolone resistance in Salmonella when the direct measurement of fluoroquinolone MICs is not feasible [corrected]. Recently updated CLSI and EUCAST susceptibility breakpoints will help to optimize clinical outcomes and reduce the likelihood of emergent resistance.
2.Interspecies scaling of excretory amounts using allometry - retrospective analysis with rifapentine, aztreonam, carumonam, pefloxacin, miloxacin, trovafloxacin, doripenem, imipenem, cefozopran, ceftazidime, linezolid for urinary excretion and rifapentine,
Srinivas NR1. Xenobiotica. 2015 Dec 29:1-9. [Epub ahead of print]
1. Interspecies allometry scaling for prediction of human excretory amounts in urine or feces was performed for numerous antibacterials. Antibacterials used for urinary scaling were: rifapentine, pefloxacin, trovafloxacin (Gr1/low; <10%); miloxacin, linezolid, PNU-142300 (Gr2/medium; 10-40%); aztreonam, carumonam, cefozopran, doripenem, imipenem, and ceftazidime (Gr3/high; >50%). Rifapentine, cabotegravir, and dolutegravir was used for fecal scaling (high; >50%). 2. The employment of allometry equation: Y = aWb enabled scaling of urine/fecal amounts from animal species. Corresponding predicted amounts were converted into % recovery by considering the respective human dose. Comparison of predicted/observed values enabled fold difference and error calculations (mean absolute error [MAE] and root mean square error [RMSE]). Comparisons were made for urinary/fecal data; and qualitative assessment was made amongst Gr1/Gr2/Gr3 for urine.
3.Development of a Pefloxacin Disk Diffusion Method for Detection of Fluoroquinolone-Resistant Salmonella enterica.
Skov R1, Matuschek E2, Sjölund-Karlsson M3, Åhman J2, Petersen A4, Stegger M4, Torpdahl M4, Kahlmeter G2. J Clin Microbiol. 2015 Nov;53(11):3411-7. doi: 10.1128/JCM.01287-15. Epub 2015 Aug 19.
Fluoroquinolones (FQs) are among the drugs of choice for treatment of Salmonella infections. However, fluoroquinolone resistance is increasing in Salmonella due to chromosomal mutations in the quinolone resistance-determining regions (QRDRs) of the topoisomerase genes gyrA, gyrB, parC, and parE and/or plasmid-mediated quinolone resistance (PMQR) mechanisms including qnr variants, aac(6')-Ib-cr, qepA, and oqxAB. Some of these mutations cause only subtle increases in the MIC, i.e., MICs ranging from 0.12 to 0.25 mg/liter for ciprofloxacin (just above the wild-type MIC of ≤0.06 mg/liter). These isolates are difficult to detect with standard ciprofloxacin disk diffusion, and plasmid-mediated resistance, such as qnr, is often not detected by the nalidixic acid screen test. We evaluated 16 quinolone/fluoroquinolone disks for their ability to detect low-level-resistant Salmonella enterica isolates that are not serotype Typhi. A total of 153 Salmonella isolates characterized for the presence (n = 104) or absence (n = 49) of gyrA and/or parC topoisomerase mutations, qnrA, qnrB, qnrD, qnrS, aac(6')-Ib-cr, or qepA genes were investigated.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
