GARENOXACIN MESYLATE ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H20F2N2O4.CH4O3S
Molecular Weight	522.518
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of GARENOXACIN MESYLATE ANHYDROUS

Structure Search

SMILES

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=UPHLDCUEQOTSAD-RFVHGSKJSA-N

InChI=1S/C23H20F2N2O4.CH4O3S/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)/t11-;/m1./s1

HIDE SMILES / InChI

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

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

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 The drug was withdrawn from the market in Europe and was never approved in the USA.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 1.14886076E12
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 1.14886076E12
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 1.14886076E12

PubMed

Title	Date	PubMed
In vitro and in vivo antimicrobial activities of T-3811ME, a novel des-F(6)-quinolone.	1999 May	10223917
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
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
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004 Apr	15047530
In vitro susceptibility of Mycobacterium tuberculosis clinical isolates to garenoxacin and DA-7867.	2005 Oct	16189119
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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 00:24:26 UTC 2023` Edited by `admin` on `Sat Dec 16 00:24:26 UTC 2023`
Record UNII	437ZKU48CF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GARENOXACIN MESYLATE ANHYDROUS

Common Name

English

GARENOXACIN MESILATE

Common Name

English

GARENOXACIN METHANESULFONATE [MI]

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 MESYLATE

Systematic 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 (1:1)

Common Name

English

GARENOXACIN MESILATE [MART.]

Common Name

English

GARENOXACIN METHANESULFONATE

Common Name

English

(+)-GARENOXACIN MESYLATE ANHYDROUS

Common Name

English

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

Systematic Name

English

T-3811ME

Code

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

Common Name

English

Garenoxacin mesilate [WHO-DD]

Common Name

English

BMS-284756

Code

English

Code System Code Type Description

FDA UNII

437ZKU48CF

Created by admin on Sat Dec 16 00:24:26 UTC 2023 , Edited by admin on Sat Dec 16 00:24:26 UTC 2023

PRIMARY

SMS_ID

100000091570

Created by admin on Sat Dec 16 00:24:27 UTC 2023 , Edited by admin on Sat Dec 16 00:24:27 UTC 2023

PRIMARY

EVMPD

SUB25395

Created by admin on Sat Dec 16 00:24:26 UTC 2023 , Edited by admin on Sat Dec 16 00:24:26 UTC 2023

PRIMARY

CAS

223652-82-2

Created by admin on Sat Dec 16 00:24:26 UTC 2023 , Edited by admin on Sat Dec 16 00:24:26 UTC 2023

PRIMARY

MERCK INDEX

m5672

Created by admin on Sat Dec 16 00:24:27 UTC 2023 , Edited by admin on Sat Dec 16 00:24:27 UTC 2023

PRIMARY

Merck Index

EPA CompTox

DTXSID4058732

Created by admin on Sat Dec 16 00:24:26 UTC 2023 , Edited by admin on Sat Dec 16 00:24:26 UTC 2023

PRIMARY

PUBCHEM

124094

Created by admin on Sat Dec 16 00:24:27 UTC 2023 , Edited by admin on Sat Dec 16 00:24:27 UTC 2023

PRIMARY

Related Record Type Details


					V72H9867WB

GARENOXACIN

PARENT -> SALT/SOLVATE

Amount:


					OXI6EF55FR

GARENOXACIN MESYLATE

SOLVATE->ANHYDROUS

Related Record Type Details


					V72H9867WB

GARENOXACIN

ACTIVE MOIETY

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

PubMed

Patents

Sample Use Guides

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