Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H17ClFN3O3 |
| Molecular Weight | 365.787 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1CCN(C1)C2=C(Cl)C3=C(C=C2F)C(=O)C(=CN3C4CC4)C(O)=O
InChI
InChIKey=QGPKADBNRMWEQR-UHFFFAOYSA-N
InChI=1S/C17H17ClFN3O3/c18-13-14-10(5-12(19)15(13)21-4-3-8(20)6-21)16(23)11(17(24)25)7-22(14)9-1-2-9/h5,7-9H,1-4,6,20H2,(H,24,25)
| Molecular Formula | C17H17ClFN3O3 |
| Molecular Weight | 365.787 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Clinafloxacin is a broad-spectrum fluoroquinolone antibiotic that was originally developed and subsequently abandoned in the late 1990s as a human health antibiotic for respiratory diseases. Clinafloxacin displays broad-spectrum antibacterial activity against Gram-positive, Gram-negative, and anaerobic pathogens by inhibiting the bacterial regulatory enzyme DNA gyrase (IC50 = 0.92 ug/ml) as well as topoisomerase IV (IC50 = 1.62 ug/ml).
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| In vitro activity of PD 127,391, an enhanced-spectrum quinolone. | 1988 Aug |
|
| CI-960 (PD127391 or AM-1091), sparfloxacin, WIN 57273, and isepamicin activity against clinical isolates of Mycobacterium avium-intracellularae complex, M. chelonae, and M. fortuitum. | 1992 Feb |
|
| Comparative in-vitro activities of the new quinolone, Bay y 3118, and ciprofloxacin, sparfloxacin, tosufloxacin, CI-960 and CI-990. | 1993 Apr |
|
| In-vitro activity of quinolones and macrolides against mycobacteria. | 1994 Sep |
|
| Determination of MICs for Mycobacterium avium-M. intracellulare complex in liquid medium by a colorimetric method. | 1995 Jul |
|
| An in vitro investigation of the bioactivities of ciprofloxacin and the new fluoroquinolone agents clinafloxacin (CI-960) and PD 131628 against Mycobacterium tuberculosis in human macrophages. | 1995 Jul-Aug |
|
| Antimicrobial activity of CS-940, a new trifluorinated quinolone. | 1995 Oct |
|
| Structure-activity relationships of quinolone agents against mycobacteria: effect of structural modifications at the 8 position. | 1996 Oct |
|
| In vitro and in vivo activities of moxifloxacin and clinafloxacin against Mycobacterium tuberculosis. | 1998 Aug |
|
| [Pharmacokinetics and bioavailability of clinafloxacin in rats]. | 2001 Feb |
|
| Experimental study of clinafloxacin alone and in combination in the treatment of ciprofloxacin-susceptible and -resistant pneumococcal meningitis. | 2003 |
|
| Emergence of fluoroquinolone resistance among Bacteroides species. | 2003 Aug |
|
| Factors influencing fluoroquinolone resistance. | 2003 Dec |
|
| Development and mechanism of fluoroquinolone resistance in Legionella pneumophila. | 2003 Feb |
|
| Antimicrobial susceptibility profile of molecular typed cystic fibrosis Stenotrophomonas maltophilia isolates and differences with noncystic fibrosis isolates. | 2003 Feb |
|
| Maintaining fluoroquinolone class efficacy: review of influencing factors. | 2003 Jan |
|
| Activities of 13 quinolones by three susceptibility testing methods against a collection of Haemophilus influenzae isolates with different levels of susceptibility to ciprofloxacin: evidence for cross-resistance. | 2003 Jan |
|
| Antimicrobial susceptibility breakpoints and first-step parC mutations in Streptococcus pneumoniae: redefining fluoroquinolone resistance. | 2003 Jul |
|
| Maximizing efficacy and reducing the emergence of resistance. | 2003 May |
|
| Adverse drug reactions: implications for the development of fluoroquinolones. | 2003 May |
|
| Accumulation of garenoxacin by Bacteroides fragilis compared with that of five fluoroquinolones. | 2003 Oct |
|
| Fluoroquinolones as chemotherapeutics against mycobacterial infections. | 2004 |
|
| Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004 Apr |
|
| Mutant prevention concentration of nalidixic acid, ciprofloxacin, clinafloxacin, levofloxacin, norfloxacin, ofloxacin, sparfloxacin or trovafloxacin for Escherichia coli under different growth conditions. | 2004 Feb |
|
| [Synthesis and antibacterial activity of 7-(7-aminomethyl-5-azaspiro [2,4] hept-5-yl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and its analogues]. | 2004 Mar |
|
| Clinafloxacin for the treatment of bacterial endocarditis. | 2004 Mar 1 |
|
| Method for inducing experimental pneumococcal meningitis in outbred mice. | 2004 Sep 22 |
|
| In vitro activities of 11 fluoroquinolones against 226 Campylobacter jejuni strains isolated from Finnish patients, with special reference to ciprofloxacin resistance. | 2005 Dec |
|
| Toxicity of fluoroquinolone antibiotics to aquatic organisms. | 2005 Feb |
|
| Activity of the new quinolone WCK 771 against pneumococci. | 2005 Jan |
|
| The selection of resistance to and the mutagenicity of different fluoroquinolones in Staphylococcus aureus and Streptococcus pneumoniae. | 2005 Sep |
|
| 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. | 2005 Sep 5 |
|
| Comparative genomics of multidrug resistance in Acinetobacter baumannii. | 2006 Jan |
|
| Photo-chemically induced DNA effects in the comet assay with epidermal cells of SKH-1 mice after a single oral administration of different fluoroquinolones and 8-methoxypsoralen in combination with exposure to UVA. | 2006 Oct 10 |
|
| Tuberculosis chemotherapy: current drug delivery approaches. | 2006 Sep 19 |
|
| Tigecycline in the treatment of complicated intra-abdominal and complicated skin and skin structure infections. | 2007 Dec |
|
| Breakage-reunion domain of Streptococcus pneumoniae topoisomerase IV: crystal structure of a gram-positive quinolone target. | 2007 Mar 21 |
|
| Clinical review: balancing the therapeutic, safety, and economic issues underlying effective antipseudomonal carbapenem use. | 2008 |
|
| An overview of harms associated with beta-lactam antimicrobials: where do the carbapenems fit in? | 2008 |
|
| Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008 Dec |
|
| Sitafloxacin hydrate for bacterial infections. | 2008 Jul |
|
| Synthesis and antibacterial activity of novel pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid derivatives carrying the 3-cyclopropylaminomethyl-4-substituted-1-pyrrolidinyl group as a C-10 substituent. | 2008 Jun 12 |
|
| HPLC Method for Determination of Enantiomeric Purity of a Novel Respiratory Fluoroquinolone: WCK 1152. | 2008 May-Jun |
|
| Quinolones: action and resistance updated. | 2009 |
|
| Structural insight into the quinolone-DNA cleavage complex of type IIA topoisomerases. | 2009 Jun |
|
| Characterization of the quinolone resistant determining regions in clinical isolates of pneumococci collected in Canada. | 2010 Jan 18 |
|
| Real-time visualization of photochemically induced fluorescence of 8-halogenated quinolones: lomefloxacin, clinafloxacin and Bay3118 in live human HaCaT keratinocytes. | 2010 Jul-Aug |
|
| Modified intention to treat reporting in randomised controlled trials: systematic review. | 2010 Jun 14 |
|
| Effects of moxifloxacin and clinafloxacin on murine limb buds cultured in regular and in magnesium-deficient medium. | 2010 Mar |
|
| Relationship of cellular topoisomerase IIα inhibition to cytotoxicity and published genotoxicity of fluoroquinolone antibiotics in V79 cells. | 2013 Apr 25 |
Patents
Sample Use Guides
Patients were treated with clinafloxacin (200 mg iv q12h or, if known or suspected of being infected with more-resistant pathogens, 400 mg q12h).
Route of Administration:
Intravenous
In Vitro Use Guide
Curator's Comment: Typical MICs for α-streptococci are 0.06–0.12 ug/mL. MIC90 values for methicillin-resistant Staphylococcus aureus (MRSA) average 1.0 ug/mL. The MIC90 for enterococci is typically 0.5 ug/mL https://www.ncbi.nlm.nih.gov/pubmed/14986244
The MIC90 values for clinafloxacin against bovine P. multocida, M. haemolytica, Histophilus somni, and M. bovis were 0.125, 0.5, 0.125, and 1 ug/ml, respectively.
| Substance Class |
Chemical
Created
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on
Edited
Fri Dec 15 16:30:41 GMT 2023
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Fri Dec 15 16:30:41 GMT 2023
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| Record UNII |
8N86XTF9QD
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| Record Status |
Validated (UNII)
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| Record Version |
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C795
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C74372
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DB14025
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100000084295
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
