WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 328337
CAS#: 123447-62-1
Description: Prulifloxacin, also known as NM-441, is an inhibitor of bacterial DNA gyrase used to treat urinary tract infections. Prulifloxacin is an oral fluoroquinolone with a broad in vitro activity spectrum against Gram positive and negative bacteria and among fluoroquinolones has the lowest power of inducing resistance. In vitro and in vivo studies have shown its clinical efficacy and pathogen eradication.
MedKoo Cat#: 328337
Name: Prulifloxacin
CAS#: 123447-62-1
Chemical Formula: C21H20FN3O6S
Exact Mass: 461.1057
Molecular Weight: 461.4644
Elemental Analysis: C, 54.66; H, 4.37; F, 4.12; N, 9.11; O, 20.80; S, 6.95
Synonym: Prulifloxacin; NM-441; NM 441; NM441
IUPAC/Chemical Name: 6-fluoro-1-methyl-7-(4-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)piperazin-1-yl)-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid
InChi Key: PWNMXPDKBYZCOO-UHFFFAOYSA-N
InChi Code: InChI=1S/C21H20FN3O6S/c1-10-16(31-21(29)30-10)9-23-3-5-24(6-4-23)15-8-14-12(7-13(15)22)18(26)17(20(27)28)19-25(14)11(2)32-19/h7-8,11H,3-6,9H2,1-2H3,(H,27,28)
SMILES Code: O=C(C1=C(SC2C)N2C3=C(C=C(F)C(N4CCN(CC5=C(C)OC(O5)=O)CC4)=C3)C1=O)O
Appearance: Solid powder
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
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: | Prulifloxacin (NM441) is an orally active fluoroquinolone antibiotic with a broad spectrum of activity against Gram-positive and -negative bacteria. |
| In vitro activity: | Minimum inhibitory concentrations (MICs) and mutant prevention concentrations (MPCs) of prulifloxacin against 30 strains of Escherichia coli isolated from urinary tract infections as well as the 'biological cost' related to acquisition of resistance to the same drug in 10 uropathogenic E. coli were assessed. In terms of MIC(90), prulifloxacin was more potent than ciprofloxacin and levofloxacin. Prulifloxacin produced lower or equal MPC values than the other two fluoroquinolones (93.3% and 73.3% compared with levofloxacin and ciprofloxacin, respectively). Reference: Int J Antimicrob Agents. 2007 Jun;29(6):679-87. https://pubmed.ncbi.nlm.nih.gov/17363225/ |
| In vivo activity: | The therapeutic effect of prulifloxacin on experimental urinary tract infection with Escherichia coli in mice was equal to that of tosufloxacin and ciprofloxacin and superior to that of ofloxacin and levofloxacin. Its therapeutic effect on Pseudomonas aeruginosa infection was equal to that of tosufloxacin and ciprofloxacin, and superior to that of ofloxacin. Against urinary tract infection with olfloxacin-resistant Enterobacter cloacae, prulifloxacin was the most effective of all the drugs tested. In conclusion, prulifloxacin (NM394) showed potent antibacterial activity against clinical isolates and potent therapeutic efficacy against experimental infection in spite of its lower AUCs compared with the reference drugs. Reference: Arzneimittelforschung. 1996 Dec;46(12):1169-73. https://pubmed.ncbi.nlm.nih.gov/9006794/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO:PBS (pH 7.2) (1:5) | 0.16 | 0.35 |
The following data is based on the product molecular weight 461.4644 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.Gualco L, Schito AM, Schito GC, Marchese A. In vitro activity of prulifloxacin against Escherichia coli isolated from urinary tract infections and the biological cost of prulifloxacin resistance. Int J Antimicrob Agents. 2007 Jun;29(6):679-87. doi: 10.1016/j.ijantimicag.2007.01.009. Epub 2007 Mar 23. PMID: 17363225. 2.Tomii Y, Ozaki M, Matsuda M, Honmura T, Nishimura I, Yamaguchi R, Adachi T, Okawa Y, Nishino T. Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice. Arzneimittelforschung. 1996 Dec;46(12):1169-73. PMID: 9006794. |
| In vitro protocol: | Gualco L, Schito AM, Schito GC, Marchese A. In vitro activity of prulifloxacin against Escherichia coli isolated from urinary tract infections and the biological cost of prulifloxacin resistance. Int J Antimicrob Agents. 2007 Jun;29(6):679-87. doi: 10.1016/j.ijantimicag.2007.01.009. Epub 2007 Mar 23. PMID: 17363225. |
| In vivo protocol: | Tomii Y, Ozaki M, Matsuda M, Honmura T, Nishimura I, Yamaguchi R, Adachi T, Okawa Y, Nishino T. Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice. Arzneimittelforschung. 1996 Dec;46(12):1169-73. PMID: 9006794. |
1: Giusti M, Blasi F, Iori I, Mazzone A, Sgambato F, Politi C, Colagrande P, Casali A, Valerio A, Gussoni G, Bonizzoni E, Campanini M. Prulifloxacin vs Levofloxacin for Exacerbation of COPD after Failure of Other Antibiotics. COPD. 2016 Oct;13(5):555-60. doi: 10.3109/15412555.2016.1152236. Epub 2016 Mar 30. PubMed PMID: 27027547.
2: Passali D, Crisanti A, Bellussi LM. Role of prulifloxacin in the treatment of acute rhinosinusitis. Infez Med. 2015 Dec;23(4):301-6. PubMed PMID: 26700078.
3: Blasi F, Schaberg T, Centanni S, Del Vecchio A, Rosignoli MT, Dionisio P. Prulifloxacin versus levofloxacin in the treatment of severe COPD patients with acute exacerbations of chronic bronchitis. Pulm Pharmacol Ther. 2013 Oct;26(5):609-16. doi: 10.1016/j.pupt.2013.03.014. Epub 2013 Mar 26. PubMed PMID: 23538168.
4: Costantini E, Zucchi A, Salvini E, Cicalese A, Li Marzi V, Filocamo MT, Bini V, Lazzeri M. Prulifloxacin vs fosfomycin for prophylaxis in female patients with recurrent UTIs: a non-inferiority trial. Int Urogynecol J. 2014 Sep;25(9):1173-8. doi: 10.1007/s00192-013-2318-1. Epub 2014 Feb 20. PubMed PMID: 24554302.
5: Locatelli M, Cifelli R, Carlucci G, Romagnoli A. Stability study of Prulifloxacin and Ulifloxacin in human plasma by HPLC-DAD. J Enzyme Inhib Med Chem. 2016;31(1):106-11. doi: 10.3109/14756366.2015.1004062. Epub 2015 Feb 16. PubMed PMID: 25683081.
6: Wu T, Fang B, Chang L, Liu M, Chen F. Sensitive determination of DNA based on the interaction between prulifloxacin-terbium(III) complex and DNA. Luminescence. 2013 Nov-Dec;28(6):894-9. doi: 10.1002/bio.2453. Epub 2013 Jan 7. PubMed PMID: 23297144.
7: Busetto GM, Giovannone R, Ferro M, Tricarico S, Del Giudice F, Matei DV, De Cobelli O, Gentile V, De Berardinis E. Chronic bacterial prostatitis: efficacy of short-lasting antibiotic therapy with prulifloxacin (Unidrox®) in association with saw palmetto extract, lactobacillus sporogens and arbutin (Lactorepens®). BMC Urol. 2014 Jul 19;14:53. doi: 10.1186/1471-2490-14-53. PubMed PMID: 25038794; PubMed Central PMCID: PMC4108969.
8: Nandi U, Roy B, Das AK, Pal TK. Correlation among the toxicity profiling (28-days repeated oral dose toxicity), toxicokinetics and tissue distribution data of ulifloxacin, the active metabolite of prulifloxacin in Wistar albino rats. Environ Toxicol Pharmacol. 2012 Sep;34(2):588-607. doi: 10.1016/j.etap.2012.07.001. Epub 2012 Jul 14. PubMed PMID: 22885677.
9: Karageorgopoulos DE, Maraki S, Vatopoulos AC, Samonis G, Schito GC, Falagas ME. Antimicrobial activity of prulifloxacin in comparison with other fluoroquinolones against community-acquired urinary and respiratory pathogens isolated in Greece. Eur J Clin Microbiol Infect Dis. 2013 Nov;32(11):1417-22. doi: 10.1007/s10096-013-1891-z. Epub 2013 May 19. PubMed PMID: 23686506.
10: Chen Y, Yang H, Lu G, Wu X, Huang W, Wu Y, Lv X, Wu G, Zhang G, Li Q, Sun Y. Prulifloxacin versus levofloxacin in the treatment of respiratory and urinary tract infections: a multicentre, double-blind, randomized controlled clinical trial. Chemotherapy. 2012;58(3):249-56. doi: 10.1159/000339718. Epub 2012 Aug 9. PubMed PMID: 22890091.
