Ofloxacine
Vue d'ensemble
Description
L’ofloxacine est un agent antibactérien synthétique de la famille des fluoroquinolones utilisé pour traiter une variété d’infections bactériennes. Elle est efficace contre les bactéries Gram-positives et Gram-négatives. L’this compound agit en inhibant la gyrase de l’ADN bactérien et la topoisomérase IV, des enzymes essentielles à la réplication, à la transcription, à la réparation et à la recombinaison de l’ADN .
Mécanisme D'action
L’ofloxacine exerce ses effets antibactériens en inhibant l’activité de la gyrase de l’ADN bactérien et de la topoisomérase IV. Ces enzymes sont cruciales pour le superenroulement et le déroulement de l’ADN bactérien, des processus nécessaires à la réplication et à la transcription de l’ADN. En inhibant ces enzymes, l’this compound empêche les bactéries de répliquer et de réparer leur ADN, ce qui entraîne la mort des cellules bactériennes .
Applications De Recherche Scientifique
L’ofloxacine a un large éventail d’applications en recherche scientifique. En chimie, elle est utilisée comme composé modèle pour étudier les mécanismes des antibiotiques fluoroquinolones. En biologie et en médecine, l’this compound est largement étudiée pour ses propriétés antibactériennes et son efficacité dans le traitement d’infections telles que la pneumonie, les infections urinaires et les infections cutanées. Elle est également utilisée dans le développement de nouveaux agents antibactériens et dans l’étude des mécanismes de résistance bactérienne .
Analyse Biochimique
Biochemical Properties
Ofloxacin plays a crucial role in biochemical reactions by targeting bacterial enzymes. It interacts primarily with DNA gyrase and topoisomerase IV, which are responsible for maintaining the supercoiling of bacterial DNA during replication and transcription . By binding to these enzymes, Ofloxacin prevents the unwinding of DNA, thereby inhibiting bacterial cell division and leading to cell death . This interaction is highly specific, with Ofloxacin having a much higher affinity for bacterial enzymes compared to their mammalian counterparts .
Cellular Effects
Ofloxacin exerts significant effects on various types of cells and cellular processes. In bacterial cells, it disrupts DNA replication and transcription, leading to the inhibition of cell division and ultimately cell death . This disruption affects cell signaling pathways, gene expression, and cellular metabolism. Ofloxacin’s impact on gene expression includes the downregulation of genes involved in DNA synthesis and repair . Additionally, it can induce the production of reactive oxygen species, further contributing to bacterial cell damage .
Molecular Mechanism
The molecular mechanism of Ofloxacin involves its binding to bacterial DNA gyrase and topoisomerase IV . By inhibiting these enzymes, Ofloxacin prevents the supercoiling and uncoiling of DNA, which are essential steps in DNA replication and transcription . This inhibition leads to the formation of double-strand breaks in the bacterial DNA, ultimately resulting in cell death . Ofloxacin’s high specificity for bacterial enzymes ensures minimal effects on mammalian cells, making it an effective antibacterial agent .
Temporal Effects in Laboratory Settings
In laboratory settings, the effects of Ofloxacin can change over time. Ofloxacin is generally stable, but its efficacy can be influenced by factors such as pH and temperature . Over time, bacterial resistance to Ofloxacin can develop, reducing its effectiveness . Long-term exposure to Ofloxacin in in vitro and in vivo studies has shown that it can lead to the selection of resistant bacterial strains . Additionally, prolonged use may result in changes in bacterial community structure and function .
Dosage Effects in Animal Models
The effects of Ofloxacin vary with different dosages in animal models. At therapeutic doses, Ofloxacin effectively treats bacterial infections without causing significant adverse effects . At higher doses, it can lead to toxic effects, including gastrointestinal disturbances, central nervous system effects, and potential damage to tendons and cartilage . Threshold effects have been observed, where doses above a certain level result in increased toxicity without additional therapeutic benefits .
Metabolic Pathways
Ofloxacin is primarily metabolized in the liver and excreted via the kidneys . The metabolic pathways involve hepatic enzymes that modify Ofloxacin into various metabolites, which are then excreted in the urine . Ofloxacin’s metabolism can affect its efficacy and toxicity, as certain metabolites may retain antibacterial activity or contribute to adverse effects . The drug’s interaction with metabolic enzymes can also influence the levels of other metabolites in the body .
Transport and Distribution
Ofloxacin is transported and distributed within cells and tissues through passive diffusion and active transport mechanisms . It can cross cell membranes and accumulate in various tissues, including the kidneys, liver, and lungs . Ofloxacin’s distribution is influenced by factors such as tissue perfusion and the presence of transport proteins . The drug’s ability to penetrate tissues and reach therapeutic concentrations is crucial for its effectiveness in treating infections .
Subcellular Localization
Within cells, Ofloxacin localizes primarily in the cytoplasm and the nucleus . Its activity is dependent on its ability to reach and interact with bacterial DNA gyrase and topoisomerase IV, which are located in the cytoplasm and associated with the bacterial chromosome . Ofloxacin’s subcellular localization is facilitated by its chemical structure, which allows it to diffuse through cell membranes and reach its target enzymes .
Méthodes De Préparation
Voies de synthèse et conditions de réaction : La synthèse de l’ofloxacine implique plusieurs étapes. Une méthode consiste à faire réagir de l’acrylate d’éthyle (N,N)-diméthylamino avec des aminopropanols dans du méthylbenzène, suivie de l’ajout d’un catalyseur de base de Lewis et de triméthylchlorosilane pour protéger les groupes hydroxyle et amido. Le mélange réactionnel est ensuite traité avec du chlorure de tétrafluorobenzoyle, suivi d’un lavage acide, d’une élimination des groupes protecteurs et d’une concentration de la phase organique pour obtenir une phase huileuse. Cette phase huileuse est ensuite traitée avec du diméthylformamide et du fluorure de potassium anhydre pour produire de l’acide difluorocarboxylique. Finalement, l’acide difluorocarboxylique réagit avec la N-méthylpipérazine dans du diméthylsulfoxyde en utilisant de la triéthylamine comme agent liant l’acide à 90-100°C pour produire de l’this compound .
Méthodes de production industrielle : La production industrielle de l’this compound implique généralement une synthèse à grande échelle utilisant des conditions de réaction similaires à celles décrites ci-dessus. Le procédé est optimisé pour un rendement et une pureté élevés, avec un contrôle précis des paramètres de réaction afin de minimiser les impuretés et de maximiser l’efficacité de la synthèse .
Analyse Des Réactions Chimiques
Types de réactions : L’ofloxacine subit diverses réactions chimiques, notamment l’oxydation, la réduction et la substitution. Par exemple, elle peut être oxydée par le sulfate de cérium(IV) en milieu acide, conduisant à la formation de différents produits d’oxydation .
Réactifs et conditions courants : Les réactifs courants utilisés dans les réactions de l’this compound comprennent le sulfate de cérium(IV) pour l’oxydation et divers solvants organiques tels que le diméthylformamide et le diméthylsulfoxyde. Les conditions de réaction impliquent souvent des températures et des niveaux de pH contrôlés pour garantir les transformations chimiques souhaitées .
Principaux produits formés : Les principaux produits formés par l’oxydation de l’this compound comprennent divers dérivés oxydés, qui peuvent être identifiés et caractérisés à l’aide de techniques telles que la chromatographie liquide haute performance et la spectrométrie de masse .
Comparaison Avec Des Composés Similaires
Composés similaires : Des composés similaires à l’ofloxacine comprennent d’autres fluoroquinolones telles que la lévthis compound, la ciprthis compound et la moxifloxacine. Ces composés partagent un mécanisme d’action similaire mais diffèrent par leur spectre d’activité et leurs propriétés pharmacocinétiques .
Unicité de l’this compound : L’this compound est unique en raison de son activité équilibrée contre les bactéries Gram-positives et Gram-négatives. Elle est également connue pour sa faible incidence d’effets secondaires par rapport à certaines autres fluoroquinolones. De plus, l’this compound a été largement étudiée et est bien documentée dans la littérature scientifique, ce qui en fait un composé précieux pour la recherche et l’utilisation clinique .
Propriétés
IUPAC Name |
7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylic acid |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C18H20FN3O4/c1-10-9-26-17-14-11(16(23)12(18(24)25)8-22(10)14)7-13(19)15(17)21-5-3-20(2)4-6-21/h7-8,10H,3-6,9H2,1-2H3,(H,24,25) |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
GSDSWSVVBLHKDQ-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C18H20FN3O4 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Related CAS |
118120-51-7 (hydrochloride) |
Source
|
| Record name | Ofloxacin [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0082419361 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
DSSTOX Substance ID |
DTXSID3041085 |
Source
|
| Record name | Ofloxacin | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID3041085 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
361.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Ofloxacin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015296 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
Soluble in aqueous solutions with pH between 2 and 5. Sparingly to slightly soluble in aqueous solutions with pH 7 (solubility falls to 4 mg/mL) and freely soluble in aqueous solutions with pH above 9., 1.44e+00 g/L |
Source
|
| Record name | Ofloxacin | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01165 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Ofloxacin | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8030 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Ofloxacin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015296 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
Ofloxacin acts on DNA gyrase and toposiomerase IV, enzymes which, like human topoisomerase, prevents the excessive supercoiling of DNA during replication or transcription. By inhibiting their function, the drug thereby inhibits normal cell division., Quinolone(s) (QNs) is widely used in infection therapy due to its good antimicrobial characteristics. However, QNs-induced arthropathy of immature animals has led to restrictions on the therapeutic use of these antimicrobial agents. The exact mechanism(s) of QNs-induced chondrotoxicity remain unknown. In the present study, .../the authors/ investigated the possible mechanism of ofloxacin (one typical QNs)-induced injuries of chondrocytes. Juvenile rabbit joint chondrocytes cultured in alginate microspheres were incubated with ofloxacin at concentrations of 0, 2, 5, 10, 20, and 40 microg/mL for up to 96 hr. Concentration of 10 microg/mL ofloxacin induced apoptosis of chondrocyte with visible apoptotic signs, including degradation of poly(ADP-ribose) polymerase, caspase-3 activation, and DNA ladder formation. Furthermore, extracellular signal-regulated kinase 1/2 (phospho-ERK1/2) and growth factor receptor-bound protein 2 (Grb2) were significantly reduced, and similar changes were also observed in the beta(1)-integrin receptor as assessed by immunoblotting. However, the mRNA level of beta(1)-integrin obtained from reverse transcription-polymerase chain reaction remained unchanged. Results of beta(1)-integrin immunoprecipitation have also shown that beta(1)-integrin did not interact with activated intracellular signaling proteins. In addition, ofloxacin did not induce apoptosis and decrease beta(1)-integrin expression in chondrocytes supplemented with Mg(2+), and the ofloxacin-induced apoptosis was caspase-8-dependent, inhibition of which did not affect the expression mode of phospho-ERK1/2 and beta(1)-integrin. Our results demonstrate that ofloxacin affects beta(1)-integrin receptor functions and the ERK mitogen-activated protein kinase signaling pathway, causing caspase-8-dependent apoptosis after exposure of 48 hr., Quinolones are widely used in infection therapy due to their good antimicrobial characteristics. However, there potential joint chondrotoxicity on immature animals has stood in the way of the therapeutic application of these agents, the exact mechanism of which is still unclear. This study was undertaken to investigate the role of oxidative damage in ofloxacin (one typical quinolones)-induced arthropathy. Chondrocytes from juvenile rabbit joints were incubated with ofloxacin at concentrations of 0, 5, 10, 20, 40 and 80 ug/mL, respectively. The extent of oxidative damage was assessed by measuring the reactive oxygen species level, activities of antioxidant enzymes, and oxidative damage to some macromolecules. It was observed that ofloxacin induced a concentration-dependent increase in intracellular reactive oxygen species production, which may be an early mediator of ofloxacin cytotoxicity. Similarly, ofloxacin resulted in a significant lipid peroxidation, revealed by a concentration-dependent increase in the level of thiobarbituric acid reactive substances. At the same time, ofloxacin induced DNA damage in a concentration-dependent manner for 24 hr measured by comet assay, which may be a cause for overproduction of reactive oxygen species. Furthermore, antioxidant enzyme activities, such as glutathione peroxidase (GPx), catalase and superoxide dismutase (SOD), were rapidly decreased after treatment with ofloxacin. In addition, SOD decline and reactive oxygen species production were strongly inhibited, and the loss in cell viability was partly abated by additional glutathione (GSH), N-acetylcysteine (NAC) and dithiothreitol (DTT). In conclusion, these results clearly demonstrated that ofloxacin could induce oxidative stress, lipid peroxidation and DNA oxidative damage to chondrocytes., Ofloxacin is a quinolone antimicrobial agent. The mechanism of action of ofloxacin and other fluoroquinolone antimicrobials involves inhibition of bacterial topoisomerase IV and DNA gyrase (both of which are type II topoisomerases), enzymes required for DNA replication, transcription, repair and recombination. Ofloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Ofloxacin is often bactericidal at concentrations equal to or slightly greater than inhibitory concentrations. Fluoroquinolones, including ofloxacin, differ in chemical structure and mode of action from aminoglycosides, macrolides and beta-lactam antibiotics, including penicillins. Fluoroquinolones may, therefore, be active against bacteria resistant to these antimicrobials. Resistance to ofloxacin due to spontaneous mutation in vitro is a rare occurrence (range: 10(-9) to 10(-11)). Although cross-resistance has been observed between ofloxacin and some other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to ofloxacin., Fluoroquinolones prolong the QT interval by blocking voltage-gated potassium channels, especially the rapid component of the delayed rectifier potassium current I(Kr), expressed by HERG (the human ether-a-go-go-related gene). According to the available case reports and clinical studies, moxifloxacin carries the greatest risk of QT prolongation from all available quinolones in clinical practice and it should be used with caution in patients with predisposing factors for Torsades de pointes (TdP). |
Source
|
| Record name | Ofloxacin | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01165 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Ofloxacin | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8030 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
Color/Form |
Off-white to pale yellow crystalline powder, Colorless needles from ethanol | |
CAS No. |
82419-36-1, 83380-47-6 |
Source
|
| Record name | Ofloxacin | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=82419-36-1 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Ofloxacin [USAN:USP:INN:BAN:JAN] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0082419361 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | Ofloxacin | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01165 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | ofloxacin | |
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| Record name | ofloxacin | |
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| Record name | Ofloxacin | |
| Source | EPA DSSTox | |
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| Record name | 7H-Pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid, 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/substance-information/-/substanceinfo/100.111.164 | |
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| Record name | (+/-)-9-Fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid | |
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| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
| Record name | OFLOXACIN | |
| Source | FDA Global Substance Registration System (GSRS) | |
| URL | https://gsrs.ncats.nih.gov/ginas/app/beta/substances/A4P49JAZ9H | |
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| Record name | Ofloxacin | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8030 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Ofloxacin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015296 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
250-257 °C (decomposes), 250 - 257 °C |
Source
|
| Record name | Ofloxacin | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB01165 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | Ofloxacin | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/8030 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Ofloxacin | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0015296 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Q1: How does Ofloxacin exert its antibacterial effect?
A1: Ofloxacin, like other fluoroquinolones, targets the A subunit of DNA gyrase (topoisomerase II) in bacteria. [] This enzyme is crucial for bacterial DNA replication and repair. By binding to DNA gyrase, Ofloxacin inhibits its activity, leading to bacterial cell death. []
Q2: Does Ofloxacin have any other targets in bacteria besides DNA gyrase?
A2: While DNA gyrase is the primary target, research suggests that Ofloxacin might also interact with other sites in bacterial cells, leading to its bactericidal action. This is supported by the observation that its bactericidal activity, unlike some other quinolones, is less affected by rifampin and cell starvation. []
Q3: What is the chemical structure of Ofloxacin?
A3: Ofloxacin ((RS)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic acid) is a racemic mixture, composed of two enantiomers: levofloxacin (the S-isomer) and D-ofloxacin (the R-isomer). [, ]
Q4: What is the molecular weight and formula of Ofloxacin?
A4: Ofloxacin has a molecular formula of C18H20FN3O4 and a molecular weight of 361.37 g/mol. [, ]
Q5: How does the presence of metal ions affect the bioavailability of Ofloxacin and Ciprofloxacin?
A5: Metal ions commonly found in ocular fluids can significantly impact the bioavailability of fluoroquinolones. Studies have shown that while the antimicrobial activity of Ofloxacin remains relatively unaffected by the ionic composition of balanced salt solutions (BSS) like BSS-Plus, the activity of Ciprofloxacin is notably reduced in the presence of such solutions. []
Q6: How does the stability of Ofloxacin injection for animals get enhanced?
A6: The stability of Ofloxacin injection for animals is improved by the addition of glacial acetic acid and glycerolformal. Glacial acetic acid acts as an acidifying agent, cosolvent, and stabilizer, enhancing Ofloxacin's solubility and stability. Glycerolformal further contributes to the injection's stability and helps increase the concentration of active components. []
Q7: How is Ofloxacin absorbed and distributed in the body?
A7: Ofloxacin exhibits 100% bioavailability, indicating complete absorption following oral administration. [] It also demonstrates a large volume of distribution, allowing it to penetrate various tissues and cells effectively. []
Q8: How is Ofloxacin metabolized and eliminated?
A8: Ofloxacin is primarily eliminated by the kidneys, with minimal liver metabolism. [, ] This characteristic results in fewer drug interactions compared to other fluoroquinolones like Ciprofloxacin. []
Q9: What are the common resistance mechanisms against Ofloxacin and other fluoroquinolones?
A10: Resistance to fluoroquinolones, including Ofloxacin, primarily arises from mutations in the bacterial DNA gyrase (gyrA) gene. [, , ] These mutations alter the binding site of the drug, reducing its efficacy. Additionally, plasmid-mediated quinolone resistance (PMQR) mechanisms have also been reported. []
Q10: Does resistance to one fluoroquinolone confer cross-resistance to others?
A11: Yes, cross-resistance among fluoroquinolones is common. Mutations in the gyrA gene often confer resistance to multiple fluoroquinolones, including Ofloxacin, Ciprofloxacin, and Levofloxacin. []
Q11: What is the significance of Nalidixic Acid resistance in predicting Ciprofloxacin susceptibility?
A12: Studies indicate that resistance to Nalidixic Acid (NA) in Salmonella species is a reliable indicator of decreased susceptibility to Ciprofloxacin. The simultaneous presence of NA resistance and reduced susceptibility to Ciprofloxacin highlights the importance of MIC determination for accurate susceptibility testing. []
Q12: What are some of the reported adverse effects associated with Ofloxacin?
A14: Ofloxacin, like other fluoroquinolones, can cause adverse effects, with the most common being gastrointestinal disturbances. Other reported side effects include central nervous system reactions, tendinitis, and tendon rupture. [, , , , ]
Q13: Are there specific risk factors that might predispose individuals to Ofloxacin-induced tendinitis?
A15: While rare, Ofloxacin-induced tendinitis has been reported. Risk factors include older age, corticosteroid therapy, history of musculoskeletal disorders, strenuous physical activity, and underlying conditions like kidney failure, diabetes, and vascular diseases. []
Q14: Can human amniotic membrane be used for Ofloxacin drug delivery in ophthalmology?
A16: Research indicates that human amniotic membrane (AM) exhibits potential as a drug delivery system for Ofloxacin in ophthalmology. Studies demonstrate that AM, when soaked in Ofloxacin ophthalmic solution, can act as a slow-release device for the drug for up to 7 hours in vitro. [] This slow-release characteristic could enhance the therapeutic benefits of AM transplantation, particularly in cases of infectious keratitis.
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