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
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+
Molecular Formula | C19H22F2N4O3 |
Molecular Weight | 392.3998 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB01208Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/nda/99/20-677S003_Zagam_Prntlbl.pdf
Sources: http://www.drugbank.ca/drugs/DB01208
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/nda/99/20-677S003_Zagam_Prntlbl.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11102735
Curator's Comment: sparfloxacin enters the brain poorly mainly because of P-glycoprotein activity at the blood-brain barrier
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4165 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11266418 |
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Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12820807 |
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Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907 |
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Target ID: CHEMBL355 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907 |
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Target ID: CHEMBL614429 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907 |
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Target ID: CHEMBL2363076 Sources: http://www.genome.jp/dbget-bin/www_bget?D00590 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Zagam Approved UseZagam (sparfloxacin) is indicated for the treatment of adults ( ≥ 18 years of age) with the following infections caused by susceptible strains of the designated microorganisms:
Community-acquired pneumonia caused by Chlamydia pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, or Streptococcus pneumoniae
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 Launch Date1996 |
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Curative | Zagam Approved UseZagam (sparfloxacin) is indicated for the treatment of adults ( ≥ 18 years of age) with the following infections caused by susceptible strains of the designated microorganisms:
Community-acquired pneumonia caused by Chlamydia pneumoniae, Haemophilus influenzae, Haemophilus parainfluenzae, Moraxella catarrhalis, Mycoplasma pneumoniae, or Streptococcus pneumoniae
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 Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.1 μg/mL |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
1.3 μg/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.7 μg × h/mL |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
20.6 μg × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20 h |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
20 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
55% |
200 mg 1 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
55% |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
SPARFLOXACIN plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 15 - 99 years n = 1585 Health Status: unhealthy Condition: infections Age Group: 15 - 99 years Sex: M+F Population Size: 1585 Sources: |
Disc. AE: Photosensitivity reaction... AEs leading to discontinuation/dose reduction: Photosensitivity reaction (11 patient) Sources: |
1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea (4 patients) Sources: Vomiting (3 patients) Headache (1 patient) Dizziness (4 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Photosensitivity reaction | 11 patient Disc. AE |
200 mg 1 times / day steady, oral Recommended Dose: 200 mg, 1 times / day Route: oral Route: steady Dose: 200 mg, 1 times / day Sources: |
unhealthy, 15 - 99 years n = 1585 Health Status: unhealthy Condition: infections Age Group: 15 - 99 years Sex: M+F Population Size: 1585 Sources: |
Headache | 1 patient | 1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 Sources: |
Vomiting | 3 patients | 1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 Sources: |
Dizziness | 4 patients | 1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 Sources: |
Nausea | 4 patients | 1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: |
healthy, adult n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 4.0 |
no | |||
yes | ||||
Page: 4.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Latest industry information on the safety profile of levofloxacin in Japan. | 2001 |
|
Biochemical effects of sparfloxacin on cell envelope of mycobacteria. | 2001 Aug |
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Activity of telithromycin against 26 quinolone-resistant pneumococci with known quinolone-resistance mechanisms. | 2001 Dec |
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[Treatment outcomes of multidrug-resistant tuberculosis--comparison between success and failure cases]. | 2001 Dec |
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A pharmacokinetic/pharmacodynamic approach to show that not all fluoroquinolones exhibit similar sensitivity toward the proconvulsant effect of biphenyl acetic acid in rats. | 2001 Dec |
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In vitro method for prediction of the phototoxic potentials of fluoroquinolones. | 2001 Dec |
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Quinolones and false-positive urine screening for opiates by immunoassay technology. | 2001 Dec 26 |
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A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia. | 2001 Nov |
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N1-phenyl substituted 4-quinolones of tuberculostatic activity. | 2001 Nov |
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Increasing resistance of Streptococcus pneumoniae to fluoroquinolones: results of a Hong Kong multicentre study in 2000. | 2001 Nov |
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Endotoxin impairs biliary transport of sparfloxacin and its glucuronide in rats. | 2001 Nov 30 |
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[Comparative study of the bacteriostatic and bactericidal activity of levofloxacin against Pasteurella strains isolated from man]. | 2001 Oct |
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Fluoroquinolone susceptibilities of efflux-mediated multidrug-resistant Pseudomonas aeruginosa, Stenotrophomonas maltophilia and Burkholderia cepacia. | 2001 Oct |
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Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus. | 2001 Sep |
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Comparison of Neisseria gonorrhoeae isolates from the genital tract and pharynx of two gonorrhea patients. | 2001 Sep |
|
In vitro susceptibilities of Bartonella and Rickettsia spp. to fluoroquinolone antibiotics as determined by immunofluorescent antibody analysis of infected Vero cell monolayers. | 2001 Sep |
|
[Sparfloxacin (a long-acting difluoroquinolone)--an antibacterial preparation with the broad spectrum activity]. | 2002 |
|
[Sparfloxacin (Sparflo) in the treatment of urological infections]. | 2002 |
|
Bactericidal activities of commonly used antiseptics against multidrug-resistant mycobacterium tuberculosis. | 2002 |
|
[Effectiveness of sparfloxacin (sparflo) in the treatment of complicated forms of pyelonephritis and prostatitis]. | 2002 |
|
A critical review of the fluoroquinolones: focus on respiratory infections. | 2002 |
|
[Prospects for development of new antituberculous drugs]. | 2002 Aug |
|
Comparative study on salivary distribution of fluoroquinolones in rats. | 2002 Aug |
|
Pharmacodynamic characterization of efflux and topoisomerase IV-mediated fluoroquinolone resistance in Streptococcus pneumoniae. | 2002 Aug |
|
Comparative antibiotic eradication of mycoplasma infections from continuous cell lines. | 2002 Feb |
|
Moxifloxacin sensitivity of respiratory pathogens in the United Kingdom. | 2002 Feb |
|
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine. | 2002 Feb |
|
Minimal inhibitory concentrations and time-kill determination of moxifloxacin against aerobic and anaerobic isolates. | 2002 Feb |
|
Elimination of mycoplasma from leukemia-lymphoma cell lines using antibiotics. | 2002 Feb |
|
Fluoroquinolones and tuberculosis. | 2002 Feb |
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Clinical toxicological aspects of fluoroquinolones. | 2002 Feb 28 |
|
[Efficacy of the sparfloxacin-ethambutol combination in a case of cerebral tuberculosis]. | 2002 Jan |
|
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae. | 2002 Jan |
|
Preparation and characterization of sparfloxacin-beta-cyclodextrin complexes. | 2002 Jul |
|
Electrochemical analysis of sparfloxacin in pharmaceutical formulation and biochemical screening of its Co(II) complex. | 2002 Jul 31 |
|
[Drug interactions between nonsteroidal anti-inflammatory drug and pazufloxacin mesilate, a new quinolone antibacterial agent for intravenous use: convulsions in mice after intravenous or intracerebroventricular administration]. | 2002 Jun |
|
[Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies]. | 2002 Jun |
|
Molecular characterization of the genes encoding DNA gyrase and topoisomerase IV of Listeria monocytogenes. | 2002 Jun |
|
Streptococcus pneumoniae, Brooklyn, New York: fluoroquinolone resistance at our doorstep. | 2002 Jun |
|
[A case report of pulmonary nocardiosis associated with bronchiectasis after pulmonary tuberculosis successfully treated with sparfloxacin]. | 2002 Mar |
|
In-vitro activity of moxifloxacin and other fluoroquinolones against Chlamydia species. | 2002 Mar |
|
Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin. | 2002 Mar |
|
Activity of clinafloxacin, compared with six other quinolones, against Acinetobacter baumannii clinical isolates. | 2002 Mar |
|
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates. | 2002 Mar |
|
Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement? | 2002 Mar 25 |
|
[Use of sparfloxacin (Sparflo) in treating complicated urologic infections]. | 2002 Mar-Apr |
|
[Pulmonary infection caused by Mycobacterium szulgai: a case report]. | 2002 May |
|
Serial passage of Chlamydia spp. in sub-inhibitory fluoroquinolone concentrations. | 2002 May |
|
A novel approach to determining physicochemical and absorption properties of 6-fluoroquinolone derivatives: experimental assessment. | 2002 May |
|
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation. | 2002 May 27 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8324151
Sparfloxacin inhibits most anaerobes at < or = 2 ug/mL
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:39:36 GMT 2023
by
admin
on
Fri Dec 15 15:39:36 GMT 2023
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Record UNII |
Q90AGA787L
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C280
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NCI_THESAURUS |
C795
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WHO-ATC |
J01MA09
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WHO-VATC |
QJ01MA09
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6612
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110871-86-8
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Sparfloxacin
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CHEMBL850
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759641
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DD-78
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C61950
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SPARFLOXACIN
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DTXSID9023590
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C061363
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2466
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Q90AGA787L
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60464
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18469
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9212
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m10132
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SUB10610MIG
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DB01208
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100000083818
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |
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