Sparfloxacin

Overview

Sparfloxacin is a fluoroquinolone antibiotic used in the treatment of bacterial infections. It has a controversial safety profile.[1] WP

It was patented in 1985 and approved for medical use in 1993. Zagam is no longer available in the United States.[2] WP

Uses, dosage and effects

Medical uses

The compound is indicated for treating community-acquired lower respiratory tract infections (acute sinusitis, exacerbations of chronic bronchitis caused by susceptible bacteria, community-acquired pneumonia).[3–6] WP

Risks and side effects

Adverse reactions

• In a review of 2081 adult patients participating in a Phase III clinical trial of sparfloxacin in community-acquired, lower respiratory tract infections, sparfloxacin (200 or 400 mg loading dose then 100 or 200 mg daily; i.e. 200/100 mg and 400/200 mg) had a similar incidence of adverse events as the comparator agents (Rubinstein, 1996). The overall rates of drug-related adverse reactions for sparfloxacin 400/200 mg versus comparators and 200/100 mg versus the comparator (amoxicillin/clavulanic acid) were 13.7 versus 17.7%, and 9.5 versus 13.2%, respectively. However, many of these reported reactions were very minor; discontinuation of the antibacterial agent because of drug-related adverse reactions occurred in 1.6 versus 1.6%, and 1) versus 1.1%, respectively. Adverse reactions affecting the nervous system were reported in 5.7% of the sparfloxacin group, with insomnia and other sleep disorders the most common events. WP
• Phototoxicity was noted in 2.0% of sparfloxacin recipients, with the average delay in onset being 6.3:t 4.5 days (range 1–14 days) after commencing sparfloxacin. Mostly this consisted of erythema on the face and hands which lasted an average of 6.4:t 4.2 days. The incidence of phototoxicity associated with sparfloxacin appears to be higher than that observed with ciprofloxacin and ofloxacin but less than that reported for fleroxacin, pefloxacin, enoxacin and nalidixic acid. WP
• Most importantly, features of the hemolytic-uremic syndrome such as that associated with temaflox have not been reported.[3][7][8][9] WP

Pharmacology

Mechanism of action

Sparfloxacin, like other quinolones and fluoroquinolones, are bactericidal drugs, actively killing bacteria. Quinolones inhibit the bacterial DNA gyrase or the topoisomerase IV enzyme, thereby inhibiting DNA replication and transcription. Quinolones can enter cells easily and therefore are often used to treat intracellular pathogens such as Legionella pneumophila and Mycoplasma pneumoniae. For many gram-negative bacteria DNA gyrase is the target, whereas topoisomerase IV is the target for many gram-positive bacteria. Eukaryotic cells do not contain DNA gyrase or topoisomerase IV. WP

Chemistry

Formula

C19H22F2N4O3 PC

CAS number

110871-86-8 PC

Molar mass (g/mol)

392.4 PC

IUPAC name (computed by PubChem)

5-amino-1-cyclopropyl-7-[(3R,5S)-3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid PC

SMILES

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

InChIKey

DZZWHBIBMUVIIW-DTORHVGOSA-N PC

PubChem CID

60464

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Psaty BM. Clinical trial design and selected drug safety issues for antibiotics used to treat community-acquired pneumonia. Clinical Infectious Diseases. December 2008. doi:10.1086/591400 · PMID 18986285 · PMC2587028
2. Other Fischer J, Ganellin CR. Analogue-based Drug Discovery. 2006
3. Journal / agency Rubinstein E. Safety profile of sparfloxacin in the treatment of respiratory tract infections. The Journal of Antimicrobial Chemotherapy. May 1996. doi:10.1093/jac/37.suppl_a.145 · PMID 8737134
4. Journal / agency Goa KL, Bryson HM, Markham A. Sparfloxacin. A review of its antibacterial activity, pharmacokinetic properties, clinical efficacy and tolerability in lower respiratory tract infections. Drugs. April 1997. doi:10.2165/00003495-199753040-00010 · PMID 9098667
5. Journal / agency Stein GE, Havlichek DH. Sparfloxacin: potential clinical and economic impact in the treatment of respiratory infections. Pharmacotherapy. 1997. doi:10.1002/j.1875-9114.1997.tb03079.x · PMID 9399598
6. Journal / agency Zhanel GG, Ennis K, Vercaigne L, Walkty A, Gin AS, Embil J, Smith H, Hoban DJ. A critical review of the fluoroquinolones: focus on respiratory infections. Drugs. 2002. doi:10.2165/00003495-200262010-00002 · PMID 11790155
7. Other Bowie et al., 1989
8. Other Davey, 1989
9. Journal / agency Wolfson JS, Hooper DC. Overview of fluoroquinolone safety. The American Journal of Medicine. December 1991. doi:10.1016/0002-9343(91)90330-z · PMID 1767803

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.