QuickView for Sparfloxacin (compound)

Summary
General Info

PubChem

PubChem Compound 11618070

Name:	sparfloxacin
PubChem Compound ID:	11618070
Molecular formula:	C₁₉H₂₂F₂N₄O₃
Molecular weight:	391.402 g/mol

DrugBank

Identification

Name:	sparfloxacin
Name (isomeric):	DB01208
Drug Type:	small molecule
Brand:	Zagam
Category:	Antitubercular Agents
CAS number:	110871-86-8

Pharmacology

Indication:	For the treatment of adults with the following infections caused by susceptible strains microorganisms: community-acquired pneumonia (caused by <i>Chlamydia pneumoniae</i>, <i>Haemophilus influenzae</i>, <i>Haemophilus parainfluenzae</i>, <i>Moraxella catarrhalis</i>, <i>Mycoplasma pneumoniae</i>, or <i>Streptococcus pneumoniae</i>) and acute bacterial exacerbations of chronic bronchitis (caused by <i>Chlamydia pneumoniae</i>, <i>Enterobacter cloacae</i>, <i>Haemophilus influenzae</i>, <i>Haemophilus parainfluenzae</i>, <i>Klebsiella pneumoniae</i>, <i>Moraxella catarrhalis</i>, <i>Staphylococcus aureus</i>, or <i>Streptococcus pneumoniae</i>).
Pharmacology:	Sparfloxacin is a synthetic fluoroquinolone broad-spectrum antimicrobial agent in the same class as ofloxacin and norfloxacin. Sparfloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an... show more » Sparfloxacin is a synthetic fluoroquinolone broad-spectrum antimicrobial agent in the same class as ofloxacin and norfloxacin. Sparfloxacin has in vitro activity against a wide range of gram-negative and gram-positive microorganisms. Sparfloxacin exerts its antibacterial activity by inhibiting DNA gyrase, a bacterial topoisomerase. DNA gyrase is an essential enzyme which controls DNA topology and assists in DNA replication, repair, deactivation, and transcription. Quinolones differ in chemical structure and mode of action from (beta)-lactam antibiotics. Quinolones may, therefore, be active against bacteria resistant to (beta)-lactam antibiotics. Although cross-resistance has been observed between sparfloxacin and other fluoroquinolones, some microorganisms resistant to other fluoroquinolones may be susceptible to sparfloxacin. In vitro tests show that the combination of sparfloxacin and rifampin is antagonistic against Staphylococcus aureus. show less «
Mechanism of Action:	The bactericidal action of sparfloxacin results from inhibition of the enzymes topoisomerase II (DNA gyrase) and topoisomerase IV, which are required for bacterial DNA replication, transcription, repair, and recombination.
Absorption:	Well absorbed following oral administration with an absolute oral bioavailability of 92%. Unaffected by administration with milk or food, however concurrent administration of antacids containing magnesium hydroxide and aluminum hydroxide reduces the oral bioavailability of sparfloxacin by as much as 50%.
Protein binding:	Low plasma protein binding in serum at about 45%.
Biotransformation:	Hepatic. Metabolized primarily by phase II glucuronidation to form a glucuronide conjugate. Metabolism does not utilize or interfere with the cytochrome P450 enzyme system.
Half Life:	Mean terminal elimination half-life of 20 hours (range 16-30 hours). Prolonged in patients with renal impairment (creatinine clearance <50 mL/min).
Toxicity:	Single doses of sparfloxacin were relatively non-toxic via the oral route of administration in mice, rats, and dogs. No deaths occurred within a 14-day post-treatment observation period at the highest oral doses tested, up to 5000 mg/kg in either rodent species, or up to 600 mg/kg in the dog. Clinical signs observed included inactivity in mice and dogs, diarrhea in both rodent species, and vomiting, salivation, and tremors in dogs.
Affected organisms:	Enteric bacteria and other eubacteria

Interactions

Drug interaction:

Erythromycin	Increased risk of cardiotoxicity and arrhythmias
Disopyramide	Increased risk of cardiotoxicity and arrhythmias
Chlorpromazine	Increased risk of cardiotoxicity and arrhythmias
Imipramine	Increased risk of cardiotoxicity and arrhythmias
Nortriptyline	Increased risk of cardiotoxicity and arrhythmias

Erythromycin	Increased risk of cardiotoxicity and arrhythmias
Disopyramide	Increased risk of cardiotoxicity and arrhythmias
Chlorpromazine	Increased risk of cardiotoxicity and arrhythmias
Imipramine	Increased risk of cardiotoxicity and arrhythmias
Nortriptyline	Increased risk of cardiotoxicity and arrhythmias
Doxepin	Increased risk of cardiotoxicity and arrhythmias
Clomipramine	Increased risk of cardiotoxicity and arrhythmias
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Promethazine	Increased risk of cardiotoxicity and arrhythmias
Desipramine	Increased risk of cardiotoxicity and arrhythmias
Perphenazine	Increased risk of cardiotoxicity and arrhythmias
Methotrimeprazine	Increased risk of cardiotoxicity and arrhythmias
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias
Amoxapine	Increased risk of cardiotoxicity and arrhythmias
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Thioridazine	Increased risk of cardiotoxicity and arrhythmias
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Bepridil	Increased risk of cardiotoxicity and arrhythmias
Prochlorperazine	Increased risk of cardiotoxicity and arrhythmias
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Astemizole	Increased risk of cardiotoxicity and arrhythmias
Calcium Acetate	Calcium salts such as calcium acetate may decrease the absorption of quinolone antibiotics such as sparfloxacin. Of concern only with oral administration of both agents. Interactions can be minimized by administering oral quinolone at least 2 hours before, or 6 hours after, the dose of an oral calcium supplement. Monitor for decreased therapeutic effects of oral quinolones if administered with oral calcium supplements.
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Amiodarone	Increased risk of cardiotoxicity and arrhythmias
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Quinidine	Increased risk of cardiotoxicity and arrhythmias
Fluphenazine	Increased risk of cardiotoxicity and arrhythmias
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution.
Amitriptyline	Increased risk of cardiotoxicity and arrhythmias
Trifluoperazine	Increased risk of cardiotoxicity and arrhythmias
Voriconazole	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).

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Targets

DNA topoisomerase 4 subunit A

DNA gyrase subunit A

DNA topoisomerase 2-alpha

Transporters

Organic cation/carnitine transporter 2

Canalicular multispecific organic anion transporter 1

Multidrug resistance protein 1