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127254-12-0 | 3-Quinolinecarboxylic acid, 7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-
CAS No: 127254-12-0 Catalog No: AG000WTZ MDL No:
Product Description
Catalog Number:
AG000WTZ
Chemical Name:
3-Quinolinecarboxylic acid, 7-[(7S)-7-amino-5-azaspiro[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-1,4-dihydro-4-oxo-
CAS Number:
127254-12-0
Molecular Formula:
C19H18ClF2N3O3
Molecular Weight:
409.8143
IUPAC Name:
7-[(7S)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-4-oxoquinoline-3-carboxylic acid
InChI:
InChI=1S/C19H18ClF2N3O3/c20-14-15-8(17(26)9(18(27)28)5-25(15)12-4-10(12)21)3-11(22)16(14)24-6-13(23)19(7-24)1-2-19/h3,5,10,12-13H,1-2,4,6-7,23H2,(H,27,28)/t10-,12+,13+/m0/s1
InChI Key:
PNUZDKCDAWUEGK-CYZMBNFOSA-N
SMILES:
F[C@H]1C[C@H]1n1cc(C(=O)O)c(=O)c2c1c(Cl)c(N1C[C@H](C3(C1)CC3)N)c(c2)F
UNII:
3GJC60U4Q8
Properties
Complexity:
761
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
409.1g/mol
Formal Charge:
0
Heavy Atom Count:
28
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
409.818g/mol
Monoisotopic Mass:
409.1g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
86.9A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.7
Literature
| Title | Journal |
|---|---|
| Impact of amino acid substitutions in B subunit of DNA gyrase in Mycobacterium leprae on fluoroquinolone resistance. | PLoS neglected tropical diseases 20121001 |
| 7-[(7S)-7-Aza-niumyl-5-aza-spiro-[2.4]hept-5-yl]-8-chloro-6-fluoro-1-[(1S,2R)-2-fluoro-cyclo-prop-yl]-4-oxo-1,4-dihydroquinoline-3-carboxyl-ate methanol monosolvate. | Acta crystallographica. Section E, Structure reports online 20120901 |
| [Helicobacter pylori-related diseases]. | Gastroenterologia y hepatologia 20120901 |
| Antimicrobial efficacies of several antibiotics against uterine cervicitis caused by Mycoplasma genitalium. | Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20120601 |
| Clinical and microbiological outcomes in treatment of men with non-gonococcal urethritis with a 100-mg twice-daily dose regimen of sitafloxacin. | Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20120601 |
| Effects of systemic sitafloxacin on periodontal infection control in elderly patients. | Gerodontology 20120601 |
| Activity of sitafloxacin against extracellular and intracellular Staphylococcus aureus in vitro and in vivo: comparison with levofloxacin and moxifloxacin. | The Journal of antibiotics 20120501 |
| Sensitivities of ciprofloxacin-resistant Mycobacterium tuberculosis clinical isolates to fluoroquinolones: role of mutant DNA gyrase subunits in drug resistance. | International journal of antimicrobial agents 20120501 |
| Correlation between variable-number tandem-repeat-based genotypes and drug susceptibility in Mycobacterium avium isolates. | European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 20120401 |
| Sitafloxacin resistance in Helicobacter pylori isolates and sitafloxacin-based triple therapy as a third-line regimen in Japan. | International journal of antimicrobial agents 20120401 |
| Rapid measurement of antituberculosis drug activity in vitro and in macrophages using bioluminescence. | The Journal of antimicrobial chemotherapy 20120201 |
| Fluoroquinolone resistance in Helicobacter pylori: role of mutations at position 87 and 91 of GyrA on the level of resistance and identification of a resistance conferring mutation in GyrB. | Helicobacter 20120201 |
| Comparative in vitro activity of sitafloxacin against bacteria isolated from Thai patients with urinary tract infections and lower respiratory tract infections. | Journal of the Medical Association of Thailand = Chotmaihet thangphaet 20120201 |
| Elucidation of the crystal structure-physicochemical property relationship among polymorphs and hydrates of sitafloxacin, a novel fluoroquinolone antibiotic. | International journal of pharmaceutics 20120117 |
| Characterization of non-stoichiometric hydration and the dehydration behavior of sitafloxacin hydrate. | Chemical & pharmaceutical bulletin 20120101 |
| Successful outcomes with oral fluoroquinolones combined with rifampicin in the treatment of Mycobacterium ulcerans: an observational cohort study. | PLoS neglected tropical diseases 20120101 |
| Prevalence of fluoroquinolone-resistant Escherichia coli O25:H4-ST131 (CTX-M-15-nonproducing) strains isolated in Japan. | Chemotherapy 20120101 |
| In vitro activity of sitafloxacin against Burkholderia pseudomallei. | International journal of antimicrobial agents 20111001 |
| [Helicobacter pylori-related diseases: dyspepsia, ulcers and gastric cancer]. | Gastroenterologia y hepatologia 20111001 |
| [Efficacy and safety of sitafloxacin for lower respiratory tract infections]. | The Japanese journal of antibiotics 20111001 |
| [Study on the safety and efficacy of sitafloxacin--results of the use-results survey]. | The Japanese journal of antibiotics 20111001 |
| Effect of gatifloxacin against Mycoplasma genitalium-related urethritis: an open clinical trial. | Sexually transmitted infections 20110801 |
| Comparison of drug sensitivity and genotypes of clinically isolated strains of levofloxacin-resistant Streptococcus pneumoniae obtained from Okinawa Island, the Japanese main island and Hong Kong. | The Journal of antibiotics 20110801 |
| [Current value of quinolones in Helicobacter pylori therapy]. | Zeitschrift fur Gastroenterologie 20110801 |
| Sitafloxacin: in bacterial infections. | Drugs 20110416 |
| Comparative in vitro and in vivo antimicrobial activities of sitafloxacin, gatifloxacin and moxifloxacin against Mycobacterium avium. | International journal of antimicrobial agents 20110401 |
| Antimicrobials & cholera: are we stranded? | The Indian journal of medical research 20110201 |
| Intensified treatment with high dose rifampicin and levofloxacin compared to standard treatment for adult patients with tuberculous meningitis (TBM-IT): protocol for a randomized controlled trial. | Trials 20110101 |
| Fluoroquinolones, the cornerstone of treatment of drug-resistant tuberculosis: a pharmacokinetic and pharmacodynamic approach. | Current pharmaceutical design 20110101 |
| Studies on mechanism of thermal crystal transformation of sitafloxacin hydrates through melting and recrystallization, yielding different anhydrates depending on initial crystalline forms. | International journal of pharmaceutics 20101215 |
| [In vitro activity of sitafloxacin against clinical isolates in 2009]. | The Japanese journal of antibiotics 20101201 |
| Changes in 12-Year First-Line Eradication Rate of Helicobacter pylori Based on Triple Therapy with Proton Pump Inhibitor, Amoxicillin and Clarithromycin. | Journal of clinical biochemistry and nutrition 20100701 |
| In vitro susceptibility to antimicrobial agents and ultrastructural characteristics related to swimming motility and drug action in Campylobacter jejuni and C. coli. | Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20100601 |
| [Susceptibility test of the Mycobacterium avium complex to sixteen anti-infective agents]. | Zhonghua jie he he hu xi za zhi = Zhonghua jiehe he huxi zazhi = Chinese journal of tuberculosis and respiratory diseases 20100501 |
| [Update on antimicrobial chemotherapy]. | Medecine et maladies infectieuses 20100301 |
| Characterization of the quinolone resistant determining regions in clinical isolates of pneumococci collected in Canada. | Annals of clinical microbiology and antimicrobials 20100101 |
| Imipenem resistance of Pseudomonas in pneumonia: a systematic literature review. | BMC pulmonary medicine 20100101 |
| A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy. | British journal of cancer 20091201 |
| [Present status and future prospect of 3rd rescue regimen for H. pylori infection]. | Nihon rinsho. Japanese journal of clinical medicine 20091201 |
| In vivo efficacy of sitafloxacin in a new murine model of non-typeable Haemophilus influenzae pneumonia by sterile intratracheal tube. | International journal of antimicrobial agents 20090901 |
| Susceptibility and bactericidal activity of 8 oral quinolones against conventional-fluoroquinolone-resistant Streptococcus pneumoniae clinical isolates. | Diagnostic microbiology and infectious disease 20090901 |
| Convulsant activity of sitafloxacin and its interactions with anti-inflammatory drugs in mice. | Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20090801 |
| Quinolones: action and resistance updated. | Current topics in medicinal chemistry 20090801 |
| [In vitro susceptibilities to levofloxacin and various antibacterial agents of 12,919 clinical isolates obtained from 72 centers in 2007]. | The Japanese journal of antibiotics 20090801 |
| [Clinical position of sitafloxacin in outpatient chemotherapy. (discussion)]. | The Japanese journal of antibiotics 20090601 |
| Comparative mutant prevention concentration and mutant selection window of sitafloxacin versus other quinolones using strains of Haemophilus influenzae with decreasing susceptibility to levofloxacin. | International journal of antimicrobial agents 20090501 |
| Quinolone-Based Third-Line Therapy for Helicobacter pylori Eradication. | Journal of clinical biochemistry and nutrition 20090301 |
| [Pharmacological profile and clinical efficacy of sitafloxacin, a novel quinolone antibacterial agent]. | Nihon yakurigaku zasshi. Folia pharmacologica Japonica 20090101 |
| Quinolones with enhanced bactericidal activity induce autolysis in Streptococcus pneumoniae. | Chemotherapy 20090101 |
| Effects of treatment with antimicrobial agents on the human colonic microflora. | Therapeutics and clinical risk management 20081201 |
| Dual-targeting properties of the 3-aminopyrrolidyl quinolones, DC-159a and sitafloxacin, against DNA gyrase and topoisomerase IV: contribution to reducing in vitro emergence of quinolone-resistant Streptococcus pneumoniae. | The Journal of antimicrobial chemotherapy 20080701 |
| Sitafloxacin hydrate for bacterial infections. | Drugs of today (Barcelona, Spain : 1998) 20080701 |
| Successful treatment of Mycobacterium ulcerans osteomyelitis with minor surgical debridement and prolonged rifampicin and ciprofloxacin therapy: a case report. | Journal of medical case reports 20080101 |
| Susceptibilities of healthcare- and community-associated methicillin-resistant staphylococci to the novel des-F(6)-quinolone DX-619. | The Journal of antimicrobial chemotherapy 20071201 |
| History and evolution of antibiotic resistance in coagulase-negative staphylococci: Susceptibility profiles of new anti-staphylococcal agents. | Therapeutics and clinical risk management 20071201 |
| Pseudomonas aeruginosa: resistance and therapeutic options at the turn of the new millennium. | Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20070601 |
| Skin and skin structure infections: treatment with newer generation fluoroquinolones. | Therapeutics and clinical risk management 20070601 |
| The potent antibacterial activity of Sitafloxacin against fluoroquinolone-resistant clinical isolates of Vibrio cholerae O1. | Microbiology and immunology 20070101 |
| In vitro activity of sitafloxacin against clinical strains of Streptococcus pneumoniae with defined amino acid substitutions in QRDRs of gyrase A and topoisomerase IV. | The Journal of antimicrobial chemotherapy 20061201 |
| [In-vitro susceptibilites to levofloxacin and various antibacterial agents of 18,639 clinical isolates obtained from 77 centers in 2004]. | The Japanese journal of antibiotics 20061201 |
| [Separation of sitafloxacin epimers by capillary electrophoresis]. | Se pu = Chinese journal of chromatography 20060901 |
| New trends in development of antimycobacterial compounds. | Infectious disorders drug targets 20060601 |
| Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101. | Toxicology in vitro : an international journal published in association with BIBRA 20060401 |
| In vitro activity of sitafloxacin compared with several fluoroquinolones against Streptococcus anginosus and Streptococcus constellatus. | International journal of antimicrobial agents 20060201 |
| Antimicrobial activity of picolinic acid against extracellular and intracellular Mycobacterium avium complex and its combined activity with clarithromycin, rifampicin and fluoroquinolones. | The Journal of antimicrobial chemotherapy 20060101 |
| Fluoroquinolones: an important class of antibiotics against tuberculosis. | Current medicinal chemistry 20060101 |
| In vitro activities of 11 fluoroquinolones against 226 Campylobacter jejuni strains isolated from Finnish patients, with special reference to ciprofloxacin resistance. | The Journal of antimicrobial chemotherapy 20051201 |
| Determination of in vitro synergy when three antimicrobial agents are combined against Mycobacterium tuberculosis. | International journal of antimicrobial agents 20051001 |
| Investigational new drugs for the treatment of resistant pneumococcal infections. | Expert opinion on investigational drugs 20050801 |
| Acyl glucuronidation of fluoroquinolone antibiotics by the UDP-glucuronosyltransferase 1A subfamily in human liver microsomes. | Drug metabolism and disposition: the biological fate of chemicals 20050601 |
| Characterization of fluoroquinolone and carbapenem susceptibilities in clinical isolates of levofloxacin-resistant Pseudomonas aeruginosa. | Chemotherapy 20050501 |
| Reproducibility of gemifloxacin and comparison fluoroquinolone MIC results using Sensititre commercial dry-form panels. | Diagnostic microbiology and infectious disease 20050301 |
| Quantitative assessment of the hepatic pharmacokinetics of the antimicrobial sitafloxacin in humans using in vivoF magnetic resonance spectroscopy. | British journal of clinical pharmacology 20050201 |
| In vitro activities of 11 fluoroquinolones against 816 non-typhoidal strains of Salmonella enterica isolated from Finnish patients with special reference to reduced ciprofloxacin susceptibility. | Annals of clinical microbiology and antimicrobials 20050101 |
| In vitro activity of older and newer fluoroquinolones against efflux-mediated high-level ciprofloxacin-resistant Streptococcus pneumoniae. | International journal of antimicrobial agents 20040801 |
| Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | Antimicrobial agents and chemotherapy 20040401 |
| In vivo experimental approach for the risk assessment of fluoroquinolone antibacterial agents-induced long QT syndrome. | European journal of pharmacology 20040220 |
| Fluoroquinolones as chemotherapeutics against mycobacterial infections. | Current pharmaceutical design 20040101 |
| Pharmacokinetics, tissue distribution, and excretion of sitafloxacin, a new fluoroquinolone antibiotic, in rats, dogs, and monkeys. | Arzneimittel-Forschung 20040101 |
| MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 2: achieving activity in vivo through the use of alternative scaffolds. | Bioorganic & medicinal chemistry letters 20031201 |
| A randomized controlled trial (volunteer study) of sitafloxacin, enoxacin, levofloxacin and sparfloxacin phototoxicity. | The British journal of dermatology 20031201 |
| Factors influencing fluoroquinolone resistance. | Emerging infectious diseases 20031201 |
| Antibacterial susceptibility of a vancomycin-resistant Staphylococcus aureus strain isolated at the Hershey Medical Center. | The Journal of antimicrobial chemotherapy 20031101 |
| A topological-substructural molecular design (TOPS-MODE) approach to determining pharmacokinetics and pharmacological properties of 6-fluoroquinolone derivatives. | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20030901 |
| Comparative antimicrobial activities of gatifloxacin, sitafloxacin and levofloxacin against Mycobacterium tuberculosis replicating within Mono Mac 6 human macrophage and A-549 type II alveolar cell lines. | The Journal of antimicrobial chemotherapy 20030801 |
| Detection of mutations in quinolone resistance-determining regions in levofloxacin- and methicillin-resistant Staphylococcus aureus: effects of the mutations on fluoroquinolone MICs. | Diagnostic microbiology and infectious disease 20030601 |
| Adverse drug reactions: implications for the development of fluoroquinolones. | The Journal of antimicrobial chemotherapy 20030501 |
| Detection of macrolide resistance in Streptococcus pneumoniae. | Chemotherapy 20030501 |
| In vitro antibacterial activity and pharmacodynamics of new quinolones. | European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 20030401 |
| Novel antibacterial agents for the treatment of serious Gram-positive infections. | Expert opinion on investigational drugs 20030301 |
| In vivo susceptibility of Mycobacterium leprae to sitafloxacin (DU-6859a), either singly or in combination with rifampicin analogues. | International journal of antimicrobial agents 20030301 |
| In-vitro activity of sitafloxacin (DU-6859a), either singly or in combination with rifampin analogs, against Mycobacterium leprae. | Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20030301 |
| Activities of sitafloxacin (DU-6859a), either singly or in combination with rifampin, against Mycobacterium ulcerans infection in mice. | Journal of chemotherapy (Florence, Italy) 20030201 |
| Pharmacological evaluation of garenoxacin, a novel des-F(6)-quinolone antimicrobial agent: effects on the central nervous system. | The Journal of toxicological sciences 20030201 |
| Sitafloxacin: DU 6859, DU 6859A, Gracevit, sitafloxacin hydrate. | Drugs in R&D 20030101 |
| Effects of disruption of heat shock genes on susceptibility of Escherichia coli to fluoroquinolones. | BMC microbiology 20030101 |
| In vitro activity of sitafloxacin (DU-6859a) alone, or in combination with rifampicin, against Mycobacterium ulcerans. | The Journal of antimicrobial chemotherapy 20021101 |
| [Prospects for development of new antituberculous drugs]. | Kekkaku : [Tuberculosis] 20020801 |
| Trends in antimicrobial susceptibility of the Streptococcus milleri group. | Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20020601 |
| In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation. | Mutation research 20020527 |
| Anti-Mycobacterium tuberculosis activities of new fluoroquinolones in combination with other antituberculous drugs. | The Journal of infection 20020401 |
| New single-isomer compounds on the horizon. | CNS spectrums 20020401 |
| In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates. | Antimicrobial agents and chemotherapy 20020301 |
| Photochemical behavior of sitafloxacin, fluoroquinolone antibiotic, in an aqueous solution. | Chemical & pharmaceutical bulletin 20020201 |
| Antimicrobial activities of clarithromycin, gatifloxacin and sitafloxacin, in combination with various antimycobacterial drugs against extracellular and intramacrophage Mycobacterium avium complex. | International journal of antimicrobial agents 20020201 |
| A critical review of the fluoroquinolones: focus on respiratory infections. | Drugs 20020101 |
| Pharmacokinetics and absolute bioavailability of sitafloxacin, a new fluoroquinolone antibiotic, in healthy male and female Caucasian subjects. | Xenobiotica; the fate of foreign compounds in biological systems 20011101 |
| A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia. | Japanese journal of pharmacology 20011101 |
| Phototoxic retinal degeneration and toxicokinetics of sitafloxacin, a quinolone antibacterial agent, in mice. | Archives of toxicology 20010901 |
| In vitro activity of sitafloxacin against Clostridium difficile. | The Journal of antimicrobial chemotherapy 20010501 |
| Inhibitory activity of quinolones against DNA gyrase of Mycobacterium tuberculosis. | The Journal of antimicrobial chemotherapy 20010401 |
| [Injectable quinolones]. | Nihon rinsho. Japanese journal of clinical medicine 20010401 |
| An open, randomised, multi-centre study comparing the safety and efficacy of sitafloxacin and imipenem/cilastatin in the intravenous treatment of hospitalised patients with pneumonia. | International journal of antimicrobial agents 20010301 |
| Comparative pharmacokinetics and pharmacodynamics of the newer fluoroquinolone antibacterials. | Clinical pharmacokinetics 20010101 |
| Recent advances in the field of quinolones. | Farmaco (Societa chimica italiana : 1989) 20010101 |
| Possible relationship between phototoxicity and photodegradation of sitafloxacin, a quinolone antibacterial agent, in the auricular skin of albino mice. | Toxicological sciences : an official journal of the Society of Toxicology 20000801 |
| Comparative in vitro antimicrobial activities of the newly synthesized quinolone HSR-903, sitafloxacin (DU-6859a), gatifloxacin (AM-1155), and levofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex. | Antimicrobial agents and chemotherapy 19991201 |
| Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae. | The Journal of antimicrobial chemotherapy 19991001 |
| [In vitro anti-MAC activities of new quinolones in focus (2)]. | Kekkaku : [Tuberculosis] 19960901 |
| In vitro and in vivo antifungal activities of DU-6859a, a fluoroquinolone, in combination with amphotericin B and fluconazole against pathogenic fungi. | Antimicrobial agents and chemotherapy 19950701 |
| Pharmacokinetics and tolerance of DU-6859a, a new fluoroquinolone, after single and multiple oral doses in healthy volunteers. | Antimicrobial agents and chemotherapy 19950101 |
| In vitro and in vivo antimycobacterial activities of a new quinolone, DU-6859a. | Antimicrobial agents and chemotherapy 19941201 |
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