Ofloxacin
Übersicht
Beschreibung
Ofloxacin ist ein synthetisches Fluorchinolon-Antibiotikum, das zur Behandlung einer Vielzahl von bakteriellen Infektionen eingesetzt wird. Es ist wirksam gegen sowohl grampositive als auch gramnegative Bakterien. This compound wirkt durch Hemmung der bakteriellen DNA-Gyrase und Topoisomerase IV, Enzyme, die für die DNA-Replikation, -Transkription, -Reparatur und -Rekombination essentiell sind .
Wirkmechanismus
Target of Action
Ofloxacin, a synthetic fluoroquinolone antibacterial agent, primarily targets bacterial DNA gyrase and topoisomerase IV . These enzymes are crucial for bacterial DNA replication as they prevent the excessive supercoiling of DNA during replication or transcription .
Mode of Action
This compound inhibits the supercoiling activity of bacterial DNA gyrase and halts DNA replication . It also acts on topoisomerase IV, preventing the excessive supercoiling of DNA during replication or transcription . By inhibiting these functions, this compound effectively inhibits normal cell division .
Biochemical Pathways
The primary biochemical pathway affected by this compound is the DNA replication pathway in bacteria. By inhibiting DNA gyrase and topoisomerase IV, this compound prevents the unwinding of DNA, which is a crucial step in DNA replication . This inhibition disrupts the normal cell division process, leading to the death of the bacterial cells .
Pharmacokinetics
This compound exhibits almost complete bioavailability (95 to 100%) . It reaches peak serum concentrations in the range of 2 to 3 mg/L after a 400mg oral dose . The average half-life of this compound is between 5 to 8 hours . Compared to other quinolones, the elimination of this compound is more dependent on renal clearance, which may necessitate dosage adjustments in patients with impaired renal function .
Result of Action
The primary result of this compound’s action is the inhibition of bacterial cell division, leading to the death of the bacterial cells . This makes this compound effective against a broad spectrum of bacterial infections, including those of the respiratory tract, kidney, skin, soft tissue, and urinary tract .
Action Environment
Environmental factors can influence the action, efficacy, and stability of this compound. For instance, pollutants such as heavy metals and microplastics can play a role in the occurrence and spread of antimicrobial pollution and antimicrobial resistance . Additionally, the pH and temperature of the environment can affect the stability and activity of this compound .
Wissenschaftliche Forschungsanwendungen
Ofloxacin hat eine breite Palette von Anwendungen in der wissenschaftlichen Forschung. In der Chemie wird es als Modellverbindung verwendet, um die Mechanismen von Fluorchinolon-Antibiotika zu untersuchen. In Biologie und Medizin wird this compound ausgiebig auf seine antibakteriellen Eigenschaften und seine Wirksamkeit bei der Behandlung von Infektionen wie Lungenentzündung, Harnwegsinfektionen und Hautinfektionen untersucht. Es wird auch bei der Entwicklung neuer Antibiotika und bei der Untersuchung von bakteriellen Resistenzmechanismen eingesetzt .
Wirkmechanismus
This compound entfaltet seine antibakterielle Wirkung durch Hemmung der Aktivität der bakteriellen DNA-Gyrase und Topoisomerase IV. Diese Enzyme sind entscheidend für die Supercoiling und Entcoiling der bakteriellen DNA, Prozesse, die für die DNA-Replikation und -Transkription notwendig sind. Durch Hemmung dieser Enzyme verhindert this compound, dass Bakterien ihre DNA replizieren und reparieren, was zum Absterben der Bakterienzellen führt .
Biochemische Analyse
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, this compound prevents the unwinding of DNA, thereby inhibiting bacterial cell division and leading to cell death . This interaction is highly specific, with this compound having a much higher affinity for bacterial enzymes compared to their mammalian counterparts .
Cellular Effects
This compound 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. This compound’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 this compound involves its binding to bacterial DNA gyrase and topoisomerase IV . By inhibiting these enzymes, this compound 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 . This compound’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 this compound can change over time. This compound is generally stable, but its efficacy can be influenced by factors such as pH and temperature . Over time, bacterial resistance to this compound can develop, reducing its effectiveness . Long-term exposure to this compound 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 this compound vary with different dosages in animal models. At therapeutic doses, this compound 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
This compound is primarily metabolized in the liver and excreted via the kidneys . The metabolic pathways involve hepatic enzymes that modify this compound into various metabolites, which are then excreted in the urine . This compound’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
This compound 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 . This compound’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, this compound 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 . This compound’s subcellular localization is facilitated by its chemical structure, which allows it to diffuse through cell membranes and reach its target enzymes .
Vorbereitungsmethoden
Synthesewege und Reaktionsbedingungen: Die Synthese von Ofloxacin umfasst mehrere Schritte. Ein Verfahren beinhaltet die Reaktion von (N,N)-Dimethylaminoethylacrylat mit Aminopropanolen in Methylbenzol, gefolgt von der Zugabe eines Lewis-Base-Katalysators und Trimethylchlorsilans zum Schutz von Hydroxyl- und Amidogruppen. Das Reaktionsgemisch wird dann mit Tetrafluorbenzoylchlorid behandelt, gefolgt von Säurewäsche, Entfernung der Schutzgruppen und Konzentrierung der organischen Schicht, um eine Ölschicht zu erhalten. Diese Ölschicht wird weiter mit Dimethylformamid und wasserfreiem Kaliumfluorid verarbeitet, um Difluorcarbonsäure zu erhalten. Schließlich reagiert Difluorcarbonsäure mit N-Methylpiperazin in Dimethylsulfoxid unter Verwendung von Triethylamin als Säurefänger bei 90-100 °C zu this compound .
Industrielle Produktionsverfahren: Die industrielle Produktion von this compound beinhaltet typischerweise die großtechnische Synthese unter ähnlichen Reaktionsbedingungen wie oben beschrieben. Der Prozess ist auf hohe Ausbeute und Reinheit optimiert, wobei die Reaktionsparameter sorgfältig gesteuert werden, um Verunreinigungen zu minimieren und die Effizienz der Synthese zu maximieren .
Analyse Chemischer Reaktionen
Reaktionstypen: Ofloxacin unterliegt verschiedenen chemischen Reaktionen, darunter Oxidation, Reduktion und Substitution. Beispielsweise kann es durch Cer(IV)-sulfat in saurem Medium oxidiert werden, was zur Bildung verschiedener Oxidationsprodukte führt .
Häufige Reagenzien und Bedingungen: Häufige Reagenzien, die bei den Reaktionen von this compound verwendet werden, sind Cer(IV)-sulfat zur Oxidation und verschiedene organische Lösungsmittel wie Dimethylformamid und Dimethylsulfoxid. Reaktionsbedingungen beinhalten häufig kontrollierte Temperaturen und pH-Werte, um die gewünschten chemischen Umwandlungen sicherzustellen .
Wichtigste gebildete Produkte: Die wichtigsten Produkte, die bei der Oxidation von this compound entstehen, sind verschiedene oxidierte Derivate, die mit Techniken wie Hochleistungsflüssigkeitschromatographie und Massenspektrometrie identifiziert und charakterisiert werden können .
Vergleich Mit ähnlichen Verbindungen
Ähnliche Verbindungen: Zu den ähnlichen Verbindungen von Ofloxacin gehören andere Fluorchinolone wie Levthis compound, Ciprthis compound und Moxifloxacin. Diese Verbindungen haben einen ähnlichen Wirkmechanismus, unterscheiden sich aber in ihrem Wirkungsspektrum und ihren pharmakokinetischen Eigenschaften .
Einzigartigkeit von this compound: this compound ist einzigartig in seiner ausgeglichenen Aktivität gegen sowohl grampositive als auch gramnegative Bakterien. Es ist auch bekannt für seine relativ geringe Nebenwirkungsrate im Vergleich zu einigen anderen Fluorchinolonen. Darüber hinaus wurde this compound ausgiebig untersucht und ist in der wissenschaftlichen Literatur gut dokumentiert, was es zu einer wertvollen Verbindung für Forschung und klinische Anwendung macht .
Eigenschaften
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
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| 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] | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0082419361 | |
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| 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. | |
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| Record name | ofloxacin | |
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| Record name | ofloxacin | |
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| Record name | Ofloxacin | |
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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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| 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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Feasible Synthetic Routes
Q1: How does Ofloxacin exert its antibacterial effect?
A1: this compound, 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, this compound inhibits its activity, leading to bacterial cell death. []
Q2: Does this compound have any other targets in bacteria besides DNA gyrase?
A2: While DNA gyrase is the primary target, research suggests that this compound 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 this compound?
A3: this compound ((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: levthis compound (the S-isomer) and D-ofloxacin (the R-isomer). [, ]
Q4: What is the molecular weight and formula of this compound?
A4: this compound 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 this compound and Ciprthis compound?
A5: Metal ions commonly found in ocular fluids can significantly impact the bioavailability of fluoroquinolones. Studies have shown that while the antimicrobial activity of this compound remains relatively unaffected by the ionic composition of balanced salt solutions (BSS) like BSS-Plus, the activity of Ciprthis compound is notably reduced in the presence of such solutions. []
Q6: How does the stability of this compound injection for animals get enhanced?
A6: The stability of this compound 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 this compound's solubility and stability. Glycerolformal further contributes to the injection's stability and helps increase the concentration of active components. []
Q7: How is this compound absorbed and distributed in the body?
A7: this compound 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 this compound metabolized and eliminated?
A8: this compound is primarily eliminated by the kidneys, with minimal liver metabolism. [, ] This characteristic results in fewer drug interactions compared to other fluoroquinolones like Ciprthis compound. []
Q9: What are the common resistance mechanisms against this compound and other fluoroquinolones?
A10: Resistance to fluoroquinolones, including this compound, 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 this compound, Ciprthis compound, and Levthis compound. []
Q11: What is the significance of Nalidixic Acid resistance in predicting Ciprthis compound susceptibility?
A12: Studies indicate that resistance to Nalidixic Acid (NA) in Salmonella species is a reliable indicator of decreased susceptibility to Ciprthis compound. The simultaneous presence of NA resistance and reduced susceptibility to Ciprthis compound highlights the importance of MIC determination for accurate susceptibility testing. []
Q12: What are some of the reported adverse effects associated with this compound?
A14: this compound, 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 this compound-induced tendinitis?
A15: While rare, this compound-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 this compound drug delivery in ophthalmology?
A16: Research indicates that human amniotic membrane (AM) exhibits potential as a drug delivery system for this compound in ophthalmology. Studies demonstrate that AM, when soaked in this compound 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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![(2R)-2-amino-5-[[hydroxy(sulfamoyloxy)phosphoryl]amino]pentanoic acid](/img/structure/B1677107.png)
