SPARFLOXACIN

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 Search

SMILES

C[C@H]1CN(C[C@@H](C)N1)C2=C(F)C3=C(C(=O)C(=CN3C4CC4)C(O)=O)C(N)=C2F

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

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase subunit A 7 Target ID: CHEMBL4165 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11266418	Inhibitor 8504
Streptococcus pneumoniae 25 Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12820807	Inhibitor 8504
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907	Inhibitor 8504
Haemophilus influenzae 10 Target ID: CHEMBL355 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907	Inhibitor 8504
Moraxella catarrhalis 10 Target ID: CHEMBL614429 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907	Inhibitor 8504
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://www.genome.jp/dbget-bin/www_bget?D00590	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Community-acquired pneumonia 47 Sources: http://www.rxlist.com/zagam-drug/indications-dosage.htm	Curative		Approved 8583	Zagam Approved Use Zagam (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 Date 1996
Chronic bronchitis 52 Sources: http://www.rxlist.com/zagam-drug/indications-dosage.htm	Curative		Approved 8583	Zagam Approved Use Zagam (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 Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
1.3 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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
1.1 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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

AUC

Value	Dose	Co-administered	Analyte	Population
20.6 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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
18.7 μg × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
20 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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
20 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
55% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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
55% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf	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

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: https://pubmed.ncbi.nlm.nih.gov/10090432/	unhealthy, 15 - 99 years Health Status: unhealthy Age Group: 15 - 99 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10090432/	Disc. AE: Photosensitivity reaction... AEs leading to discontinuation/dose reduction: Photosensitivity reaction (11 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10090432/
1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/	Other AEs: Nausea, Vomiting... Other AEs: Nausea (4 patients) Vomiting (3 patients) Headache (1 patient) Dizziness (4 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/

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: https://pubmed.ncbi.nlm.nih.gov/10090432/	unhealthy, 15 - 99 years Health Status: unhealthy Age Group: 15 - 99 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10090432/
Headache	1 patient	1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/
Vomiting	3 patients	1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/
Dizziness	4 patients	1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/
Nausea	4 patients	1600 mg single, oral Highest studied dose Dose: 1600 mg Route: oral Route: single Dose: 1600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/	healthy, adult Health Status: healthy Age Group: adult Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303 UGT 219 P-gp 2052	MRP2 146

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP2 625	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/	yes

Drug as victim

Target	Modality	Activity
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf#page=4 Page: 4.0	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11102735/	yes
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf#page=4 Page: 4.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/23711922/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9212	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9212
ChemicalBook	CB7407291	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7407291
eMolecules	499196	https://www.emolecules.com/cgi-bin/more?vid=499196
MolPort	MolPort-002-507-759	https://www.molport.com/shop/molecule-link/MolPort-002-507-759
Selleck Chemicals	sparfloxacin	http://www.selleckchem.com/products/sparfloxacin.html
ZINC	ZINC000000538362	http://zinc15.docking.org/substances/ZINC000000538362

PubMed

Title	Date	PubMed
[Prospects for development of new antituberculous drugs].	2002-08	12235850
Comparative study on salivary distribution of fluoroquinolones in rats.	2002-08	12186414
Pharmacodynamic characterization of efflux and topoisomerase IV-mediated fluoroquinolone resistance in Streptococcus pneumoniae.	2002-08	12161401
Electrochemical analysis of sparfloxacin in pharmaceutical formulation and biochemical screening of its Co(II) complex.	2002-07-31	12093511
Preparation and characterization of sparfloxacin-beta-cyclodextrin complexes.	2002-07	12168542
[Use of sparfloxacin (Sparflo) in treating complicated urologic infections].	2002-06-25	12077817
[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].	2002-06	12199111
[Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies].	2002-06	12199110
Molecular characterization of the genes encoding DNA gyrase and topoisomerase IV of Listeria monocytogenes.	2002-06	12039883
Streptococcus pneumoniae, Brooklyn, New York: fluoroquinolone resistance at our doorstep.	2002-06	12023915
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation.	2002-05-27	12034313
[Pulmonary infection caused by Mycobacterium szulgai: a case report].	2002-05	12073621
Serial passage of Chlamydia spp. in sub-inhibitory fluoroquinolone concentrations.	2002-05	12003968
A novel approach to determining physicochemical and absorption properties of 6-fluoroquinolone derivatives: experimental assessment.	2002-05	11976020
Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement?	2002-03-25	11914150
[A case report of pulmonary nocardiosis associated with bronchiectasis after pulmonary tuberculosis successfully treated with sparfloxacin].	2002-03	11974891
In-vitro activity of moxifloxacin and other fluoroquinolones against Chlamydia species.	2002-03	11957133
Possible involvement of P-glycoprotein in the biliary excretion of grepafloxacin.	2002-03	11906478
Activity of clinafloxacin, compared with six other quinolones, against Acinetobacter baumannii clinical isolates.	2002-03	11864947
In vitro antibacterial activities of DQ-113, a potent quinolone, against clinical isolates.	2002-03	11850285
Clinical toxicological aspects of fluoroquinolones.	2002-02-28	12052667
Comparative antibiotic eradication of mycoplasma infections from continuous cell lines.	2002-02	11929000
Moxifloxacin sensitivity of respiratory pathogens in the United Kingdom.	2002-02	11892894
In vitro activity of clinafloxacin in comparison with other quinolones against Stenotrophomonas maltophilia clinical isolates in the presence and absence of reserpine.	2002-02	11858908
Minimal inhibitory concentrations and time-kill determination of moxifloxacin against aerobic and anaerobic isolates.	2002-02	11850163
Elimination of mycoplasma from leukemia-lymphoma cell lines using antibiotics.	2002-02	11840296
Fluoroquinolones and tuberculosis.	2002-02	11829714
[Efficacy of the sparfloxacin-ethambutol combination in a case of cerebral tuberculosis].	2002-01	11859701
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002-01	11821174
[Sparfloxacin (a long-acting difluoroquinolone)--an antibacterial preparation with the broad spectrum activity].	2002	12077937
[Sparfloxacin (Sparflo) in the treatment of urological infections].	2002	12077935
Bactericidal activities of commonly used antiseptics against multidrug-resistant mycobacterium tuberculosis.	2002	12011515
[Effectiveness of sparfloxacin (sparflo) in the treatment of complicated forms of pyelonephritis and prostatitis].	2002	11898727
A critical review of the fluoroquinolones: focus on respiratory infections.	2002	11790155
Quinolones and false-positive urine screening for opiates by immunoassay technology.	2001-12-26	11754677
Activity of telithromycin against 26 quinolone-resistant pneumococci with known quinolone-resistance mechanisms.	2001-12	11843916
[Treatment outcomes of multidrug-resistant tuberculosis--comparison between success and failure cases].	2001-12	11806128
A pharmacokinetic/pharmacodynamic approach to show that not all fluoroquinolones exhibit similar sensitivity toward the proconvulsant effect of biphenyl acetic acid in rats.	2001-12	11733465
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.	2001-12	11698174
Endotoxin impairs biliary transport of sparfloxacin and its glucuronide in rats.	2001-11-30	11734193
A comparative study of the fluoroquinolone antibacterial agents on the action potential duration in guinea pig ventricular myocardia.	2001-11	11885973
N1-phenyl substituted 4-quinolones of tuberculostatic activity.	2001-11	11817167
Increasing resistance of Streptococcus pneumoniae to fluoroquinolones: results of a Hong Kong multicentre study in 2000.	2001-11	11679555
[Comparative study of the bacteriostatic and bactericidal activity of levofloxacin against Pasteurella strains isolated from man].	2001-10	11692747
Fluoroquinolone susceptibilities of efflux-mediated multidrug-resistant Pseudomonas aeruginosa, Stenotrophomonas maltophilia and Burkholderia cepacia.	2001-10	11581236
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.	2001-09	11810583
Comparison of Neisseria gonorrhoeae isolates from the genital tract and pharynx of two gonorrhea patients.	2001-09	11810580
In vitro susceptibilities of Bartonella and Rickettsia spp. to fluoroquinolone antibiotics as determined by immunofluorescent antibody analysis of infected Vero cell monolayers.	2001-09	11673033
[Multidrug-resistant and fluoroquinolone-resistant Salmonella enterica serotype Typhimurium definitive phage type 12 isolated from infantile diarrhea].	2001-09	11605192
Biochemical effects of sparfloxacin on cell envelope of mycobacteria.	2001-08	11811618

Patents

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:04:31 GMT 2025` Edited by `admin` on `Mon Mar 31 18:04:31 GMT 2025`
Record UNII	Q90AGA787L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ZAGAM

Preferred Name

English

SPARFLOXACIN

Official Name

English

SPARFLOXACIN [USAN]

Common Name

English

SPARFLOXACIN [MI]

Common Name

English

NSC-759641

Code

English

SPARFLOXACIN [JAN]

Common Name

English

AT-4140

Code

English

3-QUINOLINECARBOXYLIC ACID, 5-AMINO-1-CYCLOPROPYL-7-(3,5-DIMETHYL-1-PIPERAZINYL)-6,8-DIFLUORO-1,4-DIHYDRO-4-OXO-, CIS-

Systematic Name

English

Sparfloxacin [WHO-DD]

Common Name

English

SPARFLOXACIN [MART.]

Common Name

English

SPARFLOXACIN [VANDF]

Common Name

English

CI-978

Code

English

SPARFLOXACIN [ORANGE BOOK]

Common Name

English

sparfloxacin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C280