GARENOXACIN MESYLATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H20F2N2O4.CH4O3S.H2O
Molecular Weight	540.534
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CS(O)(=O)=O.C[C@H]1NCC2=CC(=CC=C12)C3=CC=C4C(=O)C(=CN(C5CC5)C4=C3OC(F)F)C(O)=O

InChI

InChIKey=IGTHEWGRXUAFKF-NVJADKKVSA-N

InChI=1S/C23H20F2N2O4.CH4O3S.H2O/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;1-5(2,3)4;/h2,5-8,10-11,14,23,26H,3-4,9H2,1H3,(H,29,30);1H3,(H,2,3,4);1H2/t11-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	C23H20F2N2O4
Molecular Weight	426.4127
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 The drug was withdrawn from the market in Europe and was never approved in the USA.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
The in vitro activity of BMS-284756, a new des-fluorinated quinolone.	2002 Jan	11751785
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.	2002 Mar	11850285
Garenoxacin (BMS-284756) and moxifloxacin in experimental meningitis caused by vancomycin-tolerant pneumococci.	2003 Jan	12499193

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:25:55 GMT 2023` Edited by `admin` on `Fri Dec 15 15:25:55 GMT 2023`
Record UNII	OXI6EF55FR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GARENOXACIN MESYLATE

Official Name

English

1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-1-METHYL-2,3-DIHYDRO-1H-5-ISOINDOLYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID MESYLATE MONOHYDRATE

Systematic Name

English

1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-1-METHYL-2,3-DIHYDRO-1H-ISOINDOL-5-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID MONOMETHANESULPHONATE MONOHYDRATE

Systematic Name

English

GARENOXACIN MESILATE HYDRATE [JAN]

Common Name

English

Garenoxacin mesilate monohydrate [WHO-DD]

Common Name

English

GARENOXACIN MESILATE MONOHYDRATE [MART.]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-2,3-DIHYDRO-1-METHYL-1H-ISOINDOL-5-YL)-1,4-DIHYDRO-4-OXO-, MONOMETHANESULFONATE, MONOHYDRATE

Common Name

English

1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-1-METHYL-2,3-DIHYDRO-1H-5-ISOINDOLYL)-4-OXO-1,4-DIHYDRO-3-QUINOLINECARBOXYLIC ACID MESILATE MONOHYDRATE

Systematic Name

English

GARENOXACIN MESILATE MONOHYDRATE

Common Name

English

1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-1-METHYL-2,3-DIHYDRO-1H-ISOINDOL-5-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID METHANESULPHONATE HYDRATE

Systematic Name

English

1-Cyclopropyl-8-(difluoromethoxy)-7-[(1R)-1-methyl-2,3-dihydro-1H-isoindol-5-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid monomethanesulfonate monohydrate

Systematic Name

English

1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-1-METHYL-2,3-DIHYDRO-1H-ISOINDOL-5-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID METHANESULFONATE HYDRATE

Systematic Name

English

BMS-284756-01

Code

English

GARENOXACIN MESILATE HYDRATE

Common Name

English

GARENOXACIN METHANESULFONATE MONOHYDRATE

Common Name

English

GARENOXACIN MESYLATE [USAN]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-2,3-DIHYDRO-1-METHYL-1H-ISOINDOL-5-YL)-1,4-DIHYDRO-4-OXO-, METHANESULFONATE, HYDRATE (1:1:1)

Common Name

English

GENINAX

Brand Name

English

GARENOXACIN METHANESULFONATE MONOHYDRATE [MI]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-8-(DIFLUOROMETHOXY)-7-((1R)-2,3-DIHYDRO-1-METHYL-1H-ISOINDOL-5-YL)-1,4-DIHYDRO-4-OXO-, METHANESULPHONATE, HYDRATE (1:1:1)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C795