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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22F2N4O3
Molecular Weight 392.3998
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SPARFLOXACIN

SMILES

C[C@H]1CN(C[C@@H](C)N1)C2=C(F)C(N)=C3C(=O)C(=CN(C4CC4)C3=C2F)C(O)=O

InChI

InChIKey=DZZWHBIBMUVIIW-DTORHVGOSA-N
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+

HIDE SMILES / InChI

Description

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. 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. Sparfloxacin is used for the treatment of adults with the following infections caused by susceptible strains microorganisms: community-acquired pneumonia (caused by Chlamydia pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, or Streptococcus pneumoniae) and acute bacterial exacerbations of chronic bronchitis (caused by Chlamydia pneumoniae, Enterobacter cloacae, Haemophilus influenzae, Haemophilus parainfluenzae, Klebsiella pneumoniae, Moraxella catarrhalis,Staphylococcus aureus, or Streptococcus pneumoniae). Sparfloxacin has trade names Spacin in Bangladesh, Zagam and Zagam Respipac. Zagam is no longer available in the United States.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Zagam
Curative
Zagam

Cmax

ValueDoseCo-administeredAnalytePopulation
1.3 μg/mL
400 mg single, oral
SPARFLOXACIN plasma
Homo sapiens
1.1 μg/mL
200 mg 1 times / day steady-state, oral
SPARFLOXACIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
20.6 μg × h/mL
400 mg single, oral
SPARFLOXACIN plasma
Homo sapiens
18.7 μg × h/mL
200 mg 1 times / day steady-state, oral
SPARFLOXACIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20 h
400 mg single, oral
SPARFLOXACIN plasma
Homo sapiens
20 h
200 mg 1 times / day steady-state, oral
SPARFLOXACIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
55%
400 mg single, oral
SPARFLOXACIN plasma
Homo sapiens
55%
200 mg 1 times / day steady-state, oral
SPARFLOXACIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended daily dose of Zagam (sparfloxacin) in patients with normal renal function is two 200-mg tablets taken on the first day as a loading dose. Thereafter, one 200-mg tablet should be taken every 24 hours for a total of 10 days of therapy (11 tablets). The recommended daily dose of Zagam (sparfloxacin) in patients with renal impairment (creatinine clearance < 50 mL/min) is two 200-mg tablets taken on the first day as a loading dose. Thereafter, one 200-mg tablet should be taken every 48 hours for a total of 9 days of therapy (6 tablets).
Route of Administration: Oral
In Vitro Use Guide
Sparfloxacin inhibits most anaerobes at < or = 2 ug/mL