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)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

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 8297
Streptococcus pneumoniae 25 Target ID: CHEMBL347 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12820807	Inhibitor 8297
Escherichia coli 82 Target ID: CHEMBL354 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907	Inhibitor 8297
Haemophilus influenzae 10 Target ID: CHEMBL355 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907	Inhibitor 8297
Moraxella catarrhalis 10 Target ID: CHEMBL614429 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11101907	Inhibitor 8297
Topoisomerase IV 62 Target ID: CHEMBL2363076 Sources: http://www.genome.jp/dbget-bin/www_bget?D00590	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Community-acquired pneumonia 47 Sources: http://www.rxlist.com/zagam-drug/indications-dosage.htm	Curative		Approved 8429	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 51 Sources: http://www.rxlist.com/zagam-drug/indications-dosage.htm	Curative		Approved 8429	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
1.1 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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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
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

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 n = 1585 Health Status: unhealthy Condition: infections Age Group: 15 - 99 years Sex: M+F Population Size: 1585 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 n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 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 n = 1585 Health Status: unhealthy Condition: infections Age Group: 15 - 99 years Sex: M+F Population Size: 1585 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 n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 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 n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 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 n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 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 n = 22 Health Status: healthy Age Group: adult Sex: M+F Population Size: 22 Sources: https://pubmed.ncbi.nlm.nih.gov/10397377/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270 UGT 192 P-gp 1537	MRP2 111

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP2 475	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/	yes

Drug as victim

Target	Modality	Activity
CYP 270	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/020677s006lbl.pdf#page=4 Page: 4.0	no
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/11102735/	yes
UGT 192	substrate 3367 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 1647	inhibitor 1626 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
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
eMolecules	499196	https://www.emolecules.com/cgi-bin/more?vid=499196

PubMed

Title	Date	PubMed
Comparison of sparfloxacin and ciprofloxacin in the treatment of community-acquired acute uncomplicated urinary tract infection in women. Sparfloxacin Multicenter Uncomplicated Urinary Tract Infection Study Group.	1999 Jun	10440621
Comparative antimicrobial activities of the newly synthesized quinolone WQ-3034, levofloxacin, sparfloxacin, and ciprofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex.	2000 Feb	10639351
Proarrhythmic effects of fluoroquinolone antibacterial agents: in vivo effects as physiologic substrate for torsades.	2000 Nov 15	11076691
Anti-toxoplasma activities of 24 quinolones and fluoroquinolones in vitro: prediction of activity by molecular topology and virtual computational techniques.	2000 Oct	10991859
Prediction of quinolone activity against Mycobacterium avium by molecular topology and virtual computational screening.	2000 Oct	10991858
Latest industry information on the safety profile of levofloxacin in Japan.	2001	11549788
Evidence of different profiles of side effects and drug-drug interactions among the quinolones--the pharmacokinetic standpoint.	2001	11549786
History of quinolones and their side effects.	2001	11549783
Effects of continuous or pulsed exposure to rifabutin and sparfloxacin on the intracellular growth of Staphylococcus aureus and Mycobacterium tuberculosis.	2001 Apr	11330364
Inhibitory activity of quinolones against DNA gyrase of Mycobacterium tuberculosis.	2001 Apr	11266418
[Treatment outcomes of multidrug-resistant tuberculosis--comparison between success and failure cases].	2001 Dec	11806128
In vitro method for prediction of the phototoxic potentials of fluoroquinolones.	2001 Dec	11698174
Quinolones and false-positive urine screening for opiates by immunoassay technology.	2001 Dec 26	11754677
Quinolones alter defense reactions mediated by macrophages.	2001 Feb	11360919
A comparison of the bactericidal activity of quinolone antibiotics in a Mycobacterium fortuitum model.	2001 Jun	11393294
Antimicrobial activity of moxifloxacin, gatifloxacin and six fluoroquinolones against Streptococcus pneumoniae.	2001 Jun	11389122
Effect of some fractions of alveolar surfactant (phospholipids and SP-A) on the bactericidal activity of different antimicrobials against some respiratory pathogens.	2001 Mar	11318808
Derivative spectrophotometric analysis of 4-quinolone antibacterials in formulations and spiked biological fluids by their Cu(II) complexes.	2001 Mar-Apr	11324600
Active intestinal secretion of new quinolone antimicrobials and the partial contribution of P-glycoprotein.	2001 May	11370709
Increasing resistance of Streptococcus pneumoniae to fluoroquinolones: results of a Hong Kong multicentre study in 2000.	2001 Nov	11679555
Fluoroquinolone susceptibilities of efflux-mediated multidrug-resistant Pseudomonas aeruginosa, Stenotrophomonas maltophilia and Burkholderia cepacia.	2001 Oct	11581236
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.	2001 Sep	11810583
Is more than one quinolone needed in clinical practice?	2001 Sep	11573860
In vitro activity of novel fluoroquinolones against Streptococcus pneumoniae isolated from children with acute otitis media.	2001 Sep-Oct	11561138
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center.	2001 Spring	11310803
[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
A critical review of the fluoroquinolones: focus on respiratory infections.	2002	11790155
[Prospects for development of new antituberculous drugs].	2002 Aug	12235850
Comparative study on salivary distribution of fluoroquinolones in rats.	2002 Aug	12186414
Moxifloxacin sensitivity of respiratory pathogens in the United Kingdom.	2002 Feb	11892894
Fluoroquinolones and tuberculosis.	2002 Feb	11829714
[Efficacy of the sparfloxacin-ethambutol combination in a case of cerebral tuberculosis].	2002 Jan	11859701
Influence of CO(2) incubation on quinolone activity against Streptococcus pneumoniae and Haemophilus influenzae.	2002 Jan	11821174
Preparation and characterization of sparfloxacin-beta-cyclodextrin complexes.	2002 Jul	12168542
Electrochemical analysis of sparfloxacin in pharmaceutical formulation and biochemical screening of its Co(II) complex.	2002 Jul 31	12093511
[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	12199111
[Phototoxicity studies of pazufloxacin mesilate, a novel parenteral quinolone antimicrobial agent--in vitro and in vivo studies].	2002 Jun	12199110
Molecular characterization of the genes encoding DNA gyrase and topoisomerase IV of Listeria monocytogenes.	2002 Jun	12039883
Activity of clinafloxacin, compared with six other quinolones, against Acinetobacter baumannii clinical isolates.	2002 Mar	11864947
[Pulmonary infection caused by Mycobacterium szulgai: a case report].	2002 May	12073621
In vitro photochemical clastogenicity of quinolone antibacterial agents studied by a chromosomal aberration test with light irradiation.	2002 May 27	12034313

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 `Fri Dec 15 15:39:36 GMT 2023` Edited by `admin` on `Fri Dec 15 15:39:36 GMT 2023`
Record UNII	Q90AGA787L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPARFLOXACIN

Official Name

English

SPARFLOXACIN [USAN]

Common Name

English

SPARFLOXACIN [MI]

Common Name

English

NSC-759641

Code

English

SPARFLOXACIN [JAN]

Common Name

English

ZAGAM

Brand 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