Ofloxacin
Ofloxacin
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Ofloxacin

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Catalog Number PR82419361
CAS 82419-36-1
Structure
Description Ofloxacin is a racemate comprising equimolar amounts of levofloxacin and dextrofloxacin. It is a synthetic fluoroquinolone antibacterial agent which inhibits the supercoiling activity of bacterial DNA gyrase, halting DNA replication.
Synonyms Floxin; Ofloxacine; Tarivid; Ocuflox; Oxaldin
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
Molecular Weight 361.4
Molecular Formula C18H20FN3O4
InChI GSDSWSVVBLHKDQ-UHFFFAOYSA-N
InChI Key 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)
Drug Categories Agents Causing Muscle Toxicity; Anti-Bacterial Agents; Anti-Infective Agents; Anti-Infective Agents, Urinary; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; BSEP/ABCB11 Substrates; Cytochrome P-450 CYP1A2 Inhibitors; Cytochrome P-450 CYP1A2 Inhibitors (strength unknown); Cytochrome P-450 Enzyme Inhibitors; Enzyme Inhibitors; Fluoroquinolones; Heterocyclic Compounds, Fused-Ring; Moderate Risk QTc-Prolonging Agents; OAT1/SLC22A6 inhibitors; Ophthalmologicals; Otologicals; QTc Prolonging Agents; Quinolines; Quinolone Antimicrobial; Quinolones; Sensory Organs; Topoisomerase II Inhibitors; Topoisomerase Inhibitors
Drug Interactions Acamprosate-The excretion of Acamprosate can be decreased when combined with Ofloxacin.
Acarbose-The therapeutic efficacy of Acarbose can be increased when used in combination with Ofloxacin.
Aceclofenac-Aceclofenac may increase the neuroexcitatory activities of Ofloxacin.
Acemetacin-Acemetacin may increase the neuroexcitatory activities of Ofloxacin.
Acenocoumarol-The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Ofloxacin.
Half-Life 9 hours
Isomeric SMILES CC1COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
Type Small Molecule
Therapeutic Category Antibacterials
Pharmacology

Indications

Ofloxacin is primarily prescribed for the management of a variety of bacterial infections, offering broad utility in clinical settings. It is effective in treating infections of the respiratory tract, kidneys, skin, soft tissues, and urinary tract. Additionally, it is employed in addressing urethral and cervical gonorrhea, highlighting its broad spectrum and versatility in combating bacterial pathogens.

Pharmacodynamics

Ofloxacin, classified as a quinolone/fluoroquinolone antibiotic, demonstrates potent bactericidal activity. It functions by disrupting bacterial DNA replication, specifically targeting an enzyme known as DNA gyrase. By binding to this enzyme, Ofloxacin prevents the necessary unwinding of the DNA helix, which is crucial for producing identical DNA strands during cell replication. The drug exhibits a remarkable selectivity with a significantly higher affinity-about 100 times greater-for bacterial DNA gyrase compared to its mammalian counterpart. Its efficacy extends to both Gram-positive and Gram-negative bacteria, making it an effective broad-spectrum antibiotic.

Absorption

The oral administration of Ofloxacin in tablet form results in high bioavailability, approximately 98%. This indicates that nearly the entire dose reaches systemic circulation, allowing for effective therapeutic concentrations with oral dosing. The efficient absorption underscores the convenience and effectiveness of Ofloxacin in treating systemic infections.

Metabolism

Upon administration, Ofloxacin undergoes hepatic metabolism, where it is processed in the liver. This metabolic pathway is crucial for the drug's elimination and plays a significant role in defining its pharmacokinetic profile. Understanding this metabolic process assists in optimizing dosing regimens and minimizing potential interactions with other hepatic-metabolized medications.

Mechanism of Action

Ofloxacin functions by targeting the bacterial enzymes DNA gyrase and topoisomerase IV. These enzymes play a critical role in managing DNA supercoiling during replication and transcription, akin to the function of human topoisomerase. By inhibiting the activity of these enzymes, Ofloxacin effectively disrupts bacterial DNA replication and transcription processes, thereby impeding normal cell division.

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