Sarafloxacin hydrochloride

Sarafloxacin hydrochloride

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Sarafloxacin hydrochloride
Category Antibiotics
Catalog number BBF-03959
CAS 91296-87-6
Molecular Weight 421.83
Molecular Formula C20H17F2N3O3.HCl
Purity >98%

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Description

Sarafloxacin is a quinolone antibiotic drug, inhibiting the topoisomerase II ligase domain. It inhibits bacterial Topo II α (DNA gyrase, topoisomerase) and is effective against Mycobacterium tuberculosis.

Specification

Synonyms Sarafloxacin HCl; A-56620; A 56620; A56620
Storage Store at 2-8°C
IUPAC Name 6-fluoro-1-(4-fluorophenyl)-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid;hydrochloride
Canonical SMILES C1CN(CCN1)C2=C(C=C3C(=C2)N(C=C(C3=O)C(=O)O)C4=CC=C(C=C4)F)F.Cl
InChI InChI=1S/C20H17F2N3O3.ClH/c21-12-1-3-13(4-2-12)25-11-15(20(27)28)19(26)14-9-16(22)18(10-17(14)25)24-7-5-23-6-8-24;/h1-4,9-11,23H,5-8H2,(H,27,28);1H
InChI Key KNWODGJQLCISLC-UHFFFAOYSA-N
Source Synthetic

Properties

Appearance Pale Yellow Solid
Antibiotic Activity Spectrum mycobacteria
Boiling Point 621.4°C at 760 mmHg
Melting Point >240°C (dec.)
Solubility Soluble in DMSO

Reference Reading

1.Determination of fluoroquinolone residues in poultry muscle in Portugal.
Pena A1, Silva LJ, Pereira A, Meisel L, Lino CM. Anal Bioanal Chem. 2010 Jul;397(6):2615-21. doi: 10.1007/s00216-010-3819-0. Epub 2010 May 22.
A total of 98 poultry samples, including chicken and turkey muscle, were analysed, using a sensitive and reliable analytical method based on liquid chromatography (LC) with spectrofluorimetric detection, for simultaneous determination of four fluoroquinolone (FQ) antibiotics, namely enrofloxacin (ENRO), ciprofloxacin (CIPRO), norfloxacin (NOR), and sarafloxacin (SARA). The method involved extraction with 0.15 mol L(-1) HCl and clean-up by solid-phase extraction using Oasis HLB cartridges. Chromatographic separation was carried out on a C(18) TSK gel column, in isocratic mode, with 0.025 mol L(-1) H(3)PO(4) solution, adjusted to pH 3.0 with tetrabutylammonium hydroxide-methanol (78:22) as mobile phase. Good linearity over the investigated concentration range was observed, with mean values of correlation coefficients higher than 0.9989 for all the analytes studied. The limits of quantification (LOQ), expressed as the lowest fortification level with acceptable precision were 15 microg kg(-1) for ENRO, CIPRO, and NOR, and 30 microg kg(-1) for SARA; these values are in compliance with requirements for monitoring of maximum residues levels (MRLs).
2.In vitro activities of tosufloxacin, temafloxacin, and A-56620 against pathogens of diarrhea.
Bryan JP1, Waters C, Sheffield J, Krieg RE, Perine PL, Wagner K. Antimicrob Agents Chemother. 1990 Feb;34(2):368-70.
Tosufloxacin (A-60969 HCl), a new quinolone with broad activity against gram-positive and anaerobic organisms, was compared in vitro with other quinolones against bacterial pathogens of diarrhea. Tosufloxacin was the most active agent against Salmonella spp., Shigella spp., Campylobacter spp., Aeromonas hydrophila, and Vibrio spp. Temafloxacin (A-62254) also demonstrated good activity against these organisms.
3.Heat-induced formulation inhomogeneity of a three-component suspension.
Toongsuwan S1, Li LC, Chang HC, Stephens D, Robinson D. Drug Dev Ind Pharm. 2004 Aug;30(7):731-7.
A suspension formulation containing sarafloxacin HCl, triamcinolone acetonide, and clotrimazole was developed for the treatment of otitis externa in dogs. The potency for the three active ingredients in this suspension was monitored at 25 degrees C and 40 degrees C for up to 3 months. The potencies of triamcinolone and clotrimazole were found unchanged, but the potency of sarafloxacin HCl in the samples stored at 40 degrees C for 1 month varied significantly between samples. However, assay inconsistency for sarafloxacin HCl was not seen in samples stored at 25 degrees C. Under an optical microscope, large crystals were found in the 40 degrees C stability samples but not in the 25 degrees C samples. The large crystals in 40 degrees C samples were identified as sarafloxacin by high-performance liquid chromatography (HPLC). This finding suggests that crystal growth of sarafloxacin took place at 40 degrees C during storage, leading to the formation of larger crystals and the consequent sampling nonuniformity and assay inconsistency.

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