Sparfloxacin

Sparfloxacin

Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a600002
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
ATC code	J01MA09 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	92%
Protein binding	45%
Metabolism	Hepatic glucuronidation system not involved
Biological half-life	16 to 30 hours
Excretion	Fecal (50%) and renal (50%)
Identifiers
IUPAC name 5-Amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid
CAS Number	110871-86-8 Y
PubChem CID	60464
DrugBank	DB01208 Y
ChemSpider	54517 Y
UNII	Q90AGA787L
KEGG	D00590 Y
ChEBI	CHEBI:9212 Y
ChEMBL	CHEMBL850 Y
ECHA InfoCard	100.157.238
Chemical and physical data
Formula	C19H22F2N4O3
Molar mass	392.41 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@@H]1CN(C[C@@H](N1)C)c2c(c(c3c(c2F)n(cc(c3=O)C(=O)O)C4CC4)N)F
InChI InChI=1S/C19H22F2N4O3/c1-8-5-24(6-9(2)23-8)17-13(20)15(22)12-16(14(17)21)25(10-3-4-10)7-11(18(12)26)19(27)28/h7-10,23H,3-6,22H2,1-2H3,(H,27,28)/t8-,9+ Y Key:DZZWHBIBMUVIIW-DTORHVGOSA-N Y

Sparfloxacin (spar FLOX a sin), trade names Spacin in Bangladesh, Zagam and Zagam Respipac, is a fluoroquinolone antibiotic used in the treatment of bacterial infections. It has a controversial safety profile. Zagam is no longer available in the United States.

Sparfloxacin is about 37-45% bound to proteins in the blood.

Shimada et al. ( 1993) has summarized many of the studies published in Japanese regarding the tissue distribution of sparfloxacin. (high concentrations are achieved in sputum, pleural fluid, skin, lung, prostate, gynecological tissues, breast milk and otolaryngological tissues. *Salivary concentrations are 66-70% of plasma levels, while CSF penetration appears to be somewhat limited with CSF:plasma concentration ratios of only 0.25-0.35.

In rabbits, sparfloxacin achieves very good penetration into the ocular vitreous (54%), cornea (76%) and lens (36%).

The compound is indicated for treating community-acquired lower respiratory tract infections (acute sinusitis, exacerbations of chronic bronchitis caused by susceptible bacteria, community-acquired pneumonia).

Sparfloxacin, like other quinolones and fluoroquinolones, are bactericidal drugs, actively killing bacteria. Quinolones inhibit the bacterial DNA gyrase or the topoisomerase IV enzyme, thereby inhibiting DNA replication and transcription. Quinolones can enter cells easily and therefore are often used to treat intracellular pathogens such as Legionella pneumophila and Mycoplasma pneumoniae. For many gram-negative bacteria DNA gyrase is the target, whereas topoisomerase IV is the target for many gram-positive bacteria. Eukaryotic cells do not contain DNA gyrase or topoisomerase IV.