Synonym
Rufloxacin HCl; Rufloxacin Hydrochloride; MF 934; Ruflox; Monos; Qari; Tebraxin; Uroflox; Uroclar;
IUPAC/Chemical Name
7-Fluoro-6-(4-methylpiperazin-1-yl)-10-oxo-4-thia-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid hydrochloride
InChi Key
LPQOADBMXVRBNX-UHFFFAOYSA-N
InChi Code
InChI=1S/C17H18FN3O3S.ClH/c1-19-2-4-20(5-3-19)14-12(18)8-10-13-16(14)25-7-6-21(13)9-11(15(10)22)17(23)24;/h8-9H,2-7H2,1H3,(H,23,24);1H
SMILES Code
O=C(C1=CN2CCSC3=C2C(C1=O)=CC(F)=C3N4CCN(C)CC4)O.[H]Cl
Appearance
A crystalline solid
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO and water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Rufloxacin is active against S. aureus, E. coli, P. aeruginosa, P. morganii, K. pneumoniae, and E. cloacae in vitro (MICs = 0.78, 0.78, 12.5, 1.56, <0.39, and <0.39 μg/ml, respectively). Rufloxacin inhibits M. luteus DNA gyrase with an IC50 value of 1.5 mM and inhibits DNA synthesis in S. aureus, E. coli, P. aeruginosa, K. pneumoniae, and E. cloacae (IC50s = 0.93, 1.03, 38.8, 0.55, and 0.66 μg/ml, respectively).
In vitro activity:
Rufloxacin significantly inhibited hOCT1-mediated uptake under initial test conditions but did not inhibit hOCT2.
Reference: Antimicrob Agents Chemother. 2013 Jun;57(6):2705-11. https://pubmed.ncbi.nlm.nih.gov/23545524/
In vivo activity:
Rufloxacin is very effective on both mouse strains, but can completely eradicate the salmonellae from livers and spleens when given early in the infection of CBA resistant mice.
Reference: J Chemother. 1992 Dec;4(6):353-7. https://pubmed.ncbi.nlm.nih.gov/1337552/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
0.1 |
0.21 |
|
| Water |
2.0 |
5.00 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
399.86
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Mulgaonkar A, Venitz J, Gründemann D, Sweet DH. Human organic cation transporters 1 (SLC22A1), 2 (SLC22A2), and 3 (SLC22A3) as disposition pathways for fluoroquinolone antimicrobials. Antimicrob Agents Chemother. 2013 Jun;57(6):2705-11. doi: 10.1128/AAC.02289-12. Epub 2013 Apr 1. PMID: 23545524; PMCID: PMC3716151.
2. Pessina A, Gribaldo L, Mineo E, Neri MG. In vitro short-term and long-term cytotoxicity of fluoroquinolones on murine cell lines. Indian J Exp Biol. 1994 Feb;32(2):113-8. PMID: 8045610.
3. Cuffini AM, Tullio V, Allocco A, Paizis G, De Leo C, Carlone NA. Effect of rufloxacin upon non-specific immune defences: in-vitro, ex-vivo and in-vivo results. J Antimicrob Chemother. 1994 Oct;34(4):545-53. doi: 10.1093/jac/34.4.545. PMID: 7868406.
4. Bonina L, Carbone M, Mastroeni P, Costa GB, Mastroeni P. Effects of rufloxacin in Salmonella typhimurium infection in mice. J Chemother. 1992 Dec;4(6):353-7. doi: 10.1080/1120009x.1992.11739191. PMID: 1337552.
In vitro protocol:
1. Mulgaonkar A, Venitz J, Gründemann D, Sweet DH. Human organic cation transporters 1 (SLC22A1), 2 (SLC22A2), and 3 (SLC22A3) as disposition pathways for fluoroquinolone antimicrobials. Antimicrob Agents Chemother. 2013 Jun;57(6):2705-11. doi: 10.1128/AAC.02289-12. Epub 2013 Apr 1. PMID: 23545524; PMCID: PMC3716151.
2. Pessina A, Gribaldo L, Mineo E, Neri MG. In vitro short-term and long-term cytotoxicity of fluoroquinolones on murine cell lines. Indian J Exp Biol. 1994 Feb;32(2):113-8. PMID: 8045610.
In vivo protocol:
1. Cuffini AM, Tullio V, Allocco A, Paizis G, De Leo C, Carlone NA. Effect of rufloxacin upon non-specific immune defences: in-vitro, ex-vivo and in-vivo results. J Antimicrob Chemother. 1994 Oct;34(4):545-53. doi: 10.1093/jac/34.4.545. PMID: 7868406.
2. Bonina L, Carbone M, Mastroeni P, Costa GB, Mastroeni P. Effects of rufloxacin in Salmonella typhimurium infection in mice. J Chemother. 1992 Dec;4(6):353-7. doi: 10.1080/1120009x.1992.11739191. PMID: 1337552.
1. Piddock, L.J.V., Panchal, S., and Norte, V. Comparison of the mechanism of action and resistance of two new fluoroquinolones, rufloxacin and MF961 with those of ofloxacin and fleroxacin in Gram-negative and Gram-positive bacteria. J. Antimicrob. Chemother. 31(6), 855-863 (1993).
2. Cecchetti, V., Fravolini, A., Fringuelli, R., et al. Quinolonecarboxylic acids. 2. Synthesis and antibacterial evaluation of 7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzothiazine-6-carboxylic acids. J. Med. Chem. 30(3), 465-473 (1987).
3. Fabbri, S., Broggini, M., Pagella, P., et al. The inhibition of supercoiling activity of DNA gyrase from Micrococcus luteus caused by rufloxacin (MF 934) and MF 961. J. Antimicrob. Chemother. 27(5), 687-689 (1991).
4. Bonina, L., Carbone, M., Mastroeni, P., et al. Effects of rufloxacin in Salmonella typhimurium infection in mice. J. Chemother. 4(6), 353-357 (1992).
5: Burgalassi S, Cappello B, Chetoni P, Iervolino M, Monti D, Saettone MF. Rufloxacin eyedrops: effect of different formulations on ocular pharmacokinetics in rabbits. Eur J Ophthalmol. 2006 Mar-Apr;16(2):311-7. doi: 10.1177/112067210601600219. PMID: 16703552.
6: Furlanetto S, Orlandini S, Porta EL, Coran S, Pinzauti S. Optimization and validation of a CZE method for rufloxacin hydrochloride determination in coated tablets. J Pharm Biomed Anal. 2002 Jun 15;28(6):1161-71. doi: 10.1016/s0731-7085(02)00054-7. PMID: 12049980.
