CLINAFLOXACIN HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H17ClFN3O3.ClH
Molecular Weight	402.248
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CLINAFLOXACIN HYDROCHLORIDE

Structure Search

SMILES

Cl.NC1CCN(C1)C2=C(Cl)C3=C(C=C2F)C(=O)C(=CN3C4CC4)C(O)=O

InChI

InChIKey=BMACYHMTJHBPOX-UHFFFAOYSA-N

InChI=1S/C17H17ClFN3O3.ClH/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);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

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	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23785362 | http://clinafloxacin.com/ | http://bioreagent.bertinpharma.com/pr10639/clinafloxacin-hydro-wbr-chloride

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

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase 26 Target ID: CHEMBL3038482 Sources: http://clinafloxacin.com/ \| https://www.ncbi.nlm.nih.gov/pubmed/18457383 \| https://www.ncbi.nlm.nih.gov/pubmed/11257024 \| https://www.ncbi.nlm.nih.gov/pubmed/10223925 \| https://www.ncbi.nlm.nih.gov/pubmed/9797208	Inhibitor 8297
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11257024 \| https://www.ncbi.nlm.nih.gov/pubmed/9797208 \| https://www.ncbi.nlm.nih.gov/pubmed/10223925	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14986244 https://www.ncbi.nlm.nih.gov/pubmed/11833836	Curative		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro activity of PD 127,391, an enhanced-spectrum quinolone.	1988 Aug	3142350
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	1315233
Comparative in-vitro activities of the new quinolone, Bay y 3118, and ciprofloxacin, sparfloxacin, tosufloxacin, CI-960 and CI-990.	1993 Apr	7605398
In-vitro activity of quinolones and macrolides against mycobacteria.	1994 Sep	7829409
Determination of MICs for Mycobacterium avium-M. intracellulare complex in liquid medium by a colorimetric method.	1995 Jul	7665657
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	7555202
Antimicrobial activity of CS-940, a new trifluorinated quinolone.	1995 Oct	8619590
Structure-activity relationships of quinolone agents against mycobacteria: effect of structural modifications at the 8 position.	1996 Oct	8891145
In vitro and in vivo activities of moxifloxacin and clinafloxacin against Mycobacterium tuberculosis.	1998 Aug	9687408
[Pharmacokinetics and bioavailability of clinafloxacin in rats].	2001 Feb	12579882
Experimental study of clinafloxacin alone and in combination in the treatment of ciprofloxacin-susceptible and -resistant pneumococcal meningitis.	2003	14633368
Emergence of fluoroquinolone resistance among Bacteroides species.	2003 Aug	12865399
Factors influencing fluoroquinolone resistance.	2003 Dec	14725310
Development and mechanism of fluoroquinolone resistance in Legionella pneumophila.	2003 Feb	12562691
Antimicrobial susceptibility profile of molecular typed cystic fibrosis Stenotrophomonas maltophilia isolates and differences with noncystic fibrosis isolates.	2003 Feb	12526070
Maintaining fluoroquinolone class efficacy: review of influencing factors.	2003 Jan	12533274
Antimicrobial susceptibility breakpoints and first-step parC mutations in Streptococcus pneumoniae: redefining fluoroquinolone resistance.	2003 Jul	12890324
Maximizing efficacy and reducing the emergence of resistance.	2003 May	12702702
Adverse drug reactions: implications for the development of fluoroquinolones.	2003 May	12702700
Accumulation of garenoxacin by Bacteroides fragilis compared with that of five fluoroquinolones.	2003 Oct	12951329
Fluoroquinolones as chemotherapeutics against mycobacterial infections.	2004	15544510
Mycobacterium tuberculosis DNA gyrase: interaction with quinolones and correlation with antimycobacterial drug activity.	2004 Apr	15047530
Mutant prevention concentration of nalidixic acid, ciprofloxacin, clinafloxacin, levofloxacin, norfloxacin, ofloxacin, sparfloxacin or trovafloxacin for Escherichia coli under different growth conditions.	2004 Feb	14688048
[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	15171652
Clinafloxacin for the treatment of bacterial endocarditis.	2004 Mar 1	14986244
Method for inducing experimental pneumococcal meningitis in outbred mice.	2004 Sep 22	15385055
In vitro activities of 11 fluoroquinolones against 226 Campylobacter jejuni strains isolated from Finnish patients, with special reference to ciprofloxacin resistance.	2005 Dec	16223936
Toxicity of fluoroquinolone antibiotics to aquatic organisms.	2005 Feb	15720004
Activity of the new quinolone WCK 771 against pneumococci.	2005 Jan	15649298
The selection of resistance to and the mutagenicity of different fluoroquinolones in Staphylococcus aureus and Streptococcus pneumoniae.	2005 Sep	16104991
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	16143044
Mutagenesis induced by 12 quinolone antibacterial agents in Escherichia coli WP2uvrA/pKM101.	2006 Apr	16171969
Comparative genomics of multidrug resistance in Acinetobacter baumannii.	2006 Jan	16415984
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	16824784
Tuberculosis chemotherapy: current drug delivery approaches.	2006 Sep 19	16984627
Tigecycline in the treatment of complicated intra-abdominal and complicated skin and skin structure infections.	2007 Dec	18516315
Breakage-reunion domain of Streptococcus pneumoniae topoisomerase IV: crystal structure of a gram-positive quinolone target.	2007 Mar 21	17375187
Clinical review: balancing the therapeutic, safety, and economic issues underlying effective antipseudomonal carbapenem use.	2008	18983709
An overview of harms associated with beta-lactam antimicrobials: where do the carbapenems fit in?	2008	18495060
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008 Dec	19337440
Sitafloxacin hydrate for bacterial infections.	2008 Jul	18806900
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	18457383
HPLC Method for Determination of Enantiomeric Purity of a Novel Respiratory Fluoroquinolone: WCK 1152.	2008 May-Jun	20046745
Quinolones: action and resistance updated.	2009	19747119
Structural insight into the quinolone-DNA cleavage complex of type IIA topoisomerases.	2009 Jun	19448616
Characterization of the quinolone resistant determining regions in clinical isolates of pneumococci collected in Canada.	2010 Jan 18	20082699
Real-time visualization of photochemically induced fluorescence of 8-halogenated quinolones: lomefloxacin, clinafloxacin and Bay3118 in live human HaCaT keratinocytes.	2010 Jul-Aug	20492567
Modified intention to treat reporting in randomised controlled trials: systematic review.	2010 Jun 14	20547685
Effects of moxifloxacin and clinafloxacin on murine limb buds cultured in regular and in magnesium-deficient medium.	2010 Mar	19949773
Relationship of cellular topoisomerase IIα inhibition to cytotoxicity and published genotoxicity of fluoroquinolone antibiotics in V79 cells.	2013 Apr 25	23340199

Patents

Sample Use Guides

In Vivo Use Guide

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

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 by `admin` on `Fri Dec 15 16:18:35 GMT 2023` Edited by `admin` on `Fri Dec 15 16:18:35 GMT 2023`
Record UNII	G17M59V0FY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLINAFLOXACIN HYDROCHLORIDE

Official Name

English

3-QUINOLINECARBOXYLIC ACID, 7-(3-AMINO-1-PYRROLIDINYL)-8-CHLORO-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-, MONOHYDROCHLORIDE, (±)-

Common Name

English

NSC-759859

Code

English

CLINAFLOXACIN HYDROCHLORIDE [MART.]

Common Name

English

(±)-7-(3-AMINO-1-PYRROLIDINYL)-8-CHLORO-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-4-OXO-3-QUINOLINECARBOXYLIC ACID, MONOHYDROCHLORIDE

Common Name

English

CLINAFLOXACIN HYDROCHLORIDE [USAN]

Common Name

English

CLINAFLOXACIN HCL

Common Name

English

CLINAFLOXACIN HYDROCHLORIDE [MI]

Common Name

English

CI-960 HCL

Code

English

Clinafloxacin hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

EVMPD

SUB13392MIG