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QuickView for Grepafloxacin (compound)
PubChem
| Name: | grepafloxacin |
|---|---|
| PubChem Compound ID: | 115008 |
| Molecular formula: | C19H25ClFN3O3 |
| Molecular weight: | 397.871 g/mol |
| Synonyms: |
161967-81-3; Grepafloxacin hydrochloride; OPC 17116; 173689-78-6; 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-, monohydrochloride; Grepafloxacin hydrochloride (+-)-; Raxar; 3-Quinolinecarboxylic acid, 1,4-dihydro-1-cyclopropyl-6-fluoro-5-methyl-7-(3-methyl-1-piperazinyl)-4-oxo-, monohydrochloride, (+-)-; Grepafloxacin Hydrochloride [USAN]
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DrugBank
Identification
| Name: | grepafloxacin |
|---|---|
| Name (isomeric): | DB00365 |
| Drug Type: | small molecule |
| Brand: | Raxar |
| Category: | Anti-Bacterial Agents, Quinolones, Antibiotics, Anti-Infectives |
| CAS number: | 119914-60-2 |
Pharmacology
| Indication: | For treatment of adults with mild to moderate infections caused by susceptible strains of <i>Haemophilus influenzae</i>, <i>Streptococcus pneumoniae</i>, or <i>Moraxella catarrhalis</i>. |
|---|---|
| Pharmacology: | Grepafloxacin has in vitro activity against a wide range of gram-positive and gram-negative aerobic microorganisms, as well as some atypical microorganisms. |
| Mechanism of Action: | Grepafloxacin exerts its antibacterial activity by inhibiting bacterial topoisomerase II (DNA gyrase) and topoisomerase IV, essential enzymes for duplication, transcription, and repair of bacterial DNA. |
| Absorption: | Rapidly and extensively absorbed following oral administration. The absolute bioavailability is approximately 70%. |
| Protein binding: | 50% |
| Biotransformation: | Primarily hepatic via CYP1A2 and CYP3A4. The major metabolite is a glucuronide conjugate; minor metabolites include sulfate conjugates and oxidative metabolites. The oxidative metabolites are formed mainly by the cytochrome P450 enzyme CYP1A2, while the cytochrome P450 enzyme CYP3A4 plays a minor role. The nonconjugated metabolites have little antimicrobial activity compared with the parent drug, and the conjugated metabolites have no antimicrobial activity |
| Half Life: | 15 ± 3 hours |
| Toxicity: | Withdrawn from the US market in 1999 due to associations with QTc prolongation and adverse cardiovascular events. |
| Affected organisms: | Enteric bacteria and other eubacteria |
Interactions
| Food interaction: |
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