SPARFLOXACIN LACTATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H22F2N4O3.C3H6O3
Molecular Weight	482.4777
Optical Activity	( + / - )
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)C(O)=O.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=ATVSJRVYWSYEGL-UFIFRZAQSA-N

InChI=1S/C19H22F2N4O3.C3H6O3/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;1-2(4)3(5)6/h7-10,23H,3-6,22H2,1-2H3,(H,27,28);2,4H,1H3,(H,5,6)/t8-,9+;

HIDE SMILES / InChI

Molecular Formula	C3H6O3
Molecular Weight	90.0779
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

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
Activity of moxifloxacin against mycobacteria.	1999 Sep	10511409
Intracellular targets of moxifloxacin: a comparison with other fluoroquinolones.	2000 May	10797078
Bactericidal assays for fluoroquinolones.	2001	11089231
Sparfloxacin in the treatment of drug resistant tuberculosis or intolerance of first line therapy.	2001 Apr	11401058
[Comparison of in vitro antimicrobial activities of ofloxacin, levofloxacin, ciprofloxacin, and sparfloxacin against various mycobacteria].	2001 Apr	11398326
Biochemical effects of sparfloxacin on cell envelope of mycobacteria.	2001 Aug	11811618
Characterization of sparfloxacin-resistant mutants of Staphylococcus aureus obtained in vitro.	2001 Aug	11516932
Quinolones alter defense reactions mediated by macrophages.	2001 Feb	11360919
The effect of pharmacokinetics on the bactericidal activity of ciprofloxacin and sparfloxacin against Streptococcus pneumoniae and the emergence of resistance.	2001 Jul	11418508
Efficacy and safety of sparfloxacin in combination with kanamycin and ethionamide in multidrug-resistant pulmonary tuberculosis patients: preliminary results.	2001 Jun	11409584
Antimicrobial resistance and serotype distribution of Streptococcus pneumoniae isolates from Crete, Greece.	2001 Jun	11397616
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
Pharmacodynamics of moxifloxacin, levofloxacin and sparfloxacin against Streptococcus pneumoniae.	2001 Jun	11389113
Biochemical mechanism of combined effect of ethambutol and sparfloxacin against Mycobacterium smegmatis.	2001 Mar	11495282
Emergence of cephem- and aztreonam-high-resistant Neisseria gonorrhoeae that does not produce beta-lactamase.	2001 Mar	11406757
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
Activity of moxifloxacin and twelve other antimicrobial agents against 216 clinical isolates of Streptococcus pneumoniae.	2001 Mar-Apr	11173809
Uptake of quinolones by in-vitro human monocyte derived macrophages.	2001 May	11370713
Active intestinal secretion of new quinolone antimicrobials and the partial contribution of P-glycoprotein.	2001 May	11370709
N1-phenyl substituted 4-quinolones of tuberculostatic activity.	2001 Nov	11817167
Spectrophotometric determination of sparfloxacin in pharmaceutical formulations using bromothymol blue.	2001 Oct	11489396
Relationship between mutations in the DNA gyrase and topoisomerase IV genes and nadifloxacin resistance in clinically isolated quinolone-resistant Staphylococcus aureus.	2001 Sep	11810583
Comparison of Neisseria gonorrhoeae isolates from the genital tract and pharynx of two gonorrhea patients.	2001 Sep	11810580
Is more than one quinolone needed in clinical practice?	2001 Sep	11573860
Molecular epidemiology and mutations at gyrA and parC genes of ciprofloxacin-resistant Escherichia coli isolates from a Taiwan medical center.	2001 Spring	11310803
Bactericidal activities of commonly used antiseptics against multidrug-resistant mycobacterium tuberculosis.	2002	12011515
[Prospects for development of new antituberculous drugs].	2002 Aug	12235850
Pharmacodynamic characterization of efflux and topoisomerase IV-mediated fluoroquinolone resistance in Streptococcus pneumoniae.	2002 Aug	12161401
Comparative antibiotic eradication of mycoplasma infections from continuous cell lines.	2002 Feb	11929000
Minimal inhibitory concentrations and time-kill determination of moxifloxacin against aerobic and anaerobic isolates.	2002 Feb	11850163
Elimination of mycoplasma from leukemia-lymphoma cell lines using antibiotics.	2002 Feb	11840296
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
[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
In-vitro activity of moxifloxacin and other fluoroquinolones against Chlamydia species.	2002 Mar	11957133
Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement?	2002 Mar 25	11914150
[Pulmonary infection caused by Mycobacterium szulgai: a case report].	2002 May	12073621
Serial passage of Chlamydia spp. in sub-inhibitory fluoroquinolone concentrations.	2002 May	12003968
A novel approach to determining physicochemical and absorption properties of 6-fluoroquinolone derivatives: experimental assessment.	2002 May	11976020

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 `Sat Dec 16 19:15:07 GMT 2023` Edited by `admin` on `Sat Dec 16 19:15:07 GMT 2023`
Record UNII	X4996GE5E2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SPARFLOXACIN LACTATE

Common Name

English

SPARFLOXACIN DL-LACTATE

Common Name

English

Sparfloxacin lactate [WHO-DD]

Common Name

English

3-Quinolinecarboxylic acid, 5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethyl-1-piperazinyl]-6,8-difluoro-1,4-dihydro-4-oxo-, rel-, 2-hydroxypropanoate (1:1)

Systematic Name

English

Code System Code Type Description

FDA UNII

X4996GE5E2

Created by admin on Sat Dec 16 19:15:08 GMT 2023 , Edited by admin on Sat Dec 16 19:15:08 GMT 2023

PRIMARY

PUBCHEM

46190847

Created by admin on Sat Dec 16 19:15:08 GMT 2023 , Edited by admin on Sat Dec 16 19:15:08 GMT 2023

PRIMARY

CAS

1362654-16-7

Created by admin on Sat Dec 16 19:15:08 GMT 2023 , Edited by admin on Sat Dec 16 19:15:08 GMT 2023

PRIMARY

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SPARFLOXACIN

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

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

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

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

C_max

T_1/2

F_unbound

Drug as perpetrator