GARENOXACIN

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

Structure Search

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

HIDE SMILES / InChI

Description
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 The drug was withdrawn from the market in Europe and was never approved in the USA.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
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://www.shijiebiaopin.net/upload/product/201233119022430.pdf	Inhibitor 8297
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: http://www.shijiebiaopin.net/upload/product/201233119022430.pdf	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Acute bacterial exacerbation of chronic bronchitis 31 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500067888.pdf	Curative	Approved 8429	GARENOXACIN MESYLATE Approved Use Acute 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.
Acute bacterial sinusitis 26 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500067888.pdf	Curative	Approved 8429	GARENOXACIN MESYLATE Approved Use Laryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis
Community-acquired pneumonia 47 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500067888.pdf	Curative	Approved 8429	GARENOXACIN MESYLATE Approved Use Acute 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.
Skin and skin structure infections 80 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500067888.pdf	Curative	Approved 8429	GARENOXACIN MESYLATE Approved Use Acute 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.
Complicated intra-abdominal infections 20 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Application_withdrawal_assessment_report/2010/01/WC500067888.pdf	Curative	Approved 8429	GARENOXACIN MESYLATE Approved Use Acute 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.
Otitis media 41 Sources: http://www.shijiebiaopin.net/upload/product/201233119022430.pdf	Curative	Approved 8429	GENINAX Approved Use Laryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis Launch Date 2006
Tonsillitis 36 Sources: http://www.shijiebiaopin.net/upload/product/201233119022430.pdf	Curative	Approved 8429	GENINAX Approved Use Laryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis Launch Date 2006
Laryngopharyngitis 3 Sources: http://www.shijiebiaopin.net/upload/product/201233119022430.pdf	Curative	Approved 8429	GENINAX Approved Use Laryngopharyngitis, Tonsillitis (including peritonsillitis and peritonsillar abscess), Acute bronchitis, Pneumonia, Secondary infection in chronic respiratory lesion, Otitis media, Sinusitis Launch Date 2006

PubMed

Title	Date	PubMed
Antibacterial spectrum of a novel des-fluoro(6) quinolone, BMS-284756.	2000 Dec	11083639
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	12572531
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004 Apr	15047530
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	19915794

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dosage is 400 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

GARENOXACIN

Official Name

English

GARENOXACIN [MI]

Common Name

English

GARENOXACIN [MART.]

Common Name

English

Garenoxacin [WHO-DD]

Common Name

English

T-3811

Code

English

garenoxacin [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ01MA19