Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H20F2N2O4 |
Molecular Weight | 426.4127 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H]1NCC2=CC(=CC=C12)C3=CC=C4C(=O)C(=CN(C5CC5)C4=C3OC(F)F)C(O)=O
InChI
InChIKey=NJDRXTDGYFKORP-LLVKDONJSA-N
InChI=1S/C23H20F2N2O4/c1-11-15-5-2-12(8-13(15)9-26-11)16-6-7-17-19(21(16)31-23(24)25)27(14-3-4-14)10-18(20(17)28)22(29)30/h2,5-8,10-11,14,23,26H,3-4,9H2,1H3,(H,29,30)/t11-/m1/s1
DescriptionSources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500067888.pdfCurator's Comment: description was created based on several sources, including, http://www.shijiebiaopin.com/upload/product/201233119022430.pdf
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500067888.pdf
Curator's Comment: description was created based on several sources, including, http://www.shijiebiaopin.com/upload/product/201233119022430.pdf
Garenoxacin is an antibacterial agent active against a range of aerobic Gram-positive and Gram-negative bacteria. It exerts its action by inhibiting bacterial DNA gyrase and topoisomerase IV. The drug was withdrawn from the market in Europe and was never approved in the USA. Garenoxacin is still marketed in Japan under the name Geninax.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2363076 |
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Target ID: CHEMBL2311224 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Curative | GARENOXACIN MESYLATE Approved UseAcute bacterial exacerbation of chronic bronchitis, Acute bacterial sinusitis, Community-acquired pneumonia, Uncomplicated skin and skin structures infections, Complicated skin and skin structure infections including diabetic foot infections, Complicated intra-abdominal infections, including post-surgical and acute pelvic infections. |
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Curative | GARENOXACIN MESYLATE Approved UseLaryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis |
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Curative | GARENOXACIN MESYLATE Approved UseAcute bacterial exacerbation of chronic bronchitis, Acute bacterial sinusitis, Community-acquired pneumonia, Uncomplicated skin and skin structures infections, Complicated skin and skin structure infections including diabetic foot infections, Complicated intra-abdominal infections, including post-surgical and acute pelvic infections. |
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Curative | GARENOXACIN MESYLATE Approved UseAcute bacterial exacerbation of chronic bronchitis, Acute bacterial sinusitis, Community-acquired pneumonia, Uncomplicated skin and skin structures infections, Complicated skin and skin structure infections including diabetic foot infections, Complicated intra-abdominal infections, including post-surgical and acute pelvic infections. |
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Curative | GARENOXACIN MESYLATE Approved UseAcute bacterial exacerbation of chronic bronchitis, Acute bacterial sinusitis, Community-acquired pneumonia, Uncomplicated skin and skin structures infections, Complicated skin and skin structure infections including diabetic foot infections, Complicated intra-abdominal infections, including post-surgical and acute pelvic infections. |
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Curative | GENINAX Approved UseLaryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis Launch Date2006 |
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Curative | GENINAX Approved UseLaryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis Launch Date2006 |
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Curative | GENINAX Approved UseLaryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis Launch Date2006 |
PubMed
Title | Date | PubMed |
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In vitro and in vivo antimicrobial activities of T-3811ME, a novel des-F(6)-quinolone. | 1999 May |
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Antibacterial spectrum of a novel des-fluoro(6) quinolone, BMS-284756. | 2000 Dec |
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Synthesis, antibacterial activity, and toxicity of 7-(isoindolin-5-yl)-4-oxoquinoline-3-carboxylic acids. Discovery of the novel des-F(6)-quinolone antibacterial agent garenoxacin (T-3811 or BMS-284756). | 2002 |
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The in vitro activity of BMS-284756, a new des-fluorinated quinolone. | 2002 Jan |
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In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates. | 2002 Mar |
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Garenoxacin (BMS-284756) and moxifloxacin in experimental meningitis caused by vancomycin-tolerant pneumococci. | 2003 Jan |
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Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity. | 2004 Apr |
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In vitro susceptibility of Mycobacterium tuberculosis clinical isolates to garenoxacin and DA-7867. | 2005 Oct |
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Torsades de Pointes induced by a combination of garenoxacin and disopyramide and other cytochrome P450, family 3, subfamily A polypeptide-4-influencing drugs during hypokalemia due to licorice. | 2010 Apr |
Patents
Sample Use Guides
The MICs was 0.025-0.78 ug/ml against aerobic and facultative anaerobic Gram-positive bacteria, 0.00313-12.5 ug/ml against aerobic and facultative anaerobic Gram-negative bacteria, 0.1-3.13 ug/ml against obligate anaerobic Gram-positive bacteria and 0.05-0.78 ug/ml for obligate Gram-negative bacteria. The MICs against C. pneumoniae, C. psittaci, M. pneumoniae and Legionella spp., were 0.008, 0.002, 0.016, 0.0313 and 0.0039-0.0313 ug/ml, respectively.
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QJ01MA19
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NCI_THESAURUS |
C795
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WHO-ATC |
J01MA19
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100000091588
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m5672
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194804-75-6
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8237
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V72H9867WB
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Garenoxacin
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C65800
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SUB25475
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DTXSID30173135
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4053
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CHEMBL215303
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C419689
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DB06160
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124093
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)