Sparfloxacin

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Sparfloxacin
Sparfloxacin.svg
Sparfloxacin-from-xtal-3D-bs-17.png
Clinical data
Pronunciationspar FLOX a sin
Trade names Spacin, Zagam, others
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a600002
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 92%
Protein binding 45%
Metabolism Hepatic glucuronidation
Cytochrome P450 system not involved
Elimination half-life 16 to 30 hours
Excretion Fecal (50%) and renal (50%)
Identifiers
  • 5-Amino-1-cyclopropyl-7-[(3R,5S)3,5-dimethylpiperazin-1-yl]-6,8-difluoro-4-oxo-quinoline-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.157.238 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H22F2N4O3
Molar mass 392.407 g·mol−1
3D model (JSmol)
Melting point 266 to 269 °C (511 to 516 °F) (dec.)
  • C[C@@H]1CN(C[C@@H](N1)C)c2c(c(c3c(c2F)n(cc(c3=O)C(=O)O)C4CC4)N)F
  • 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+ Yes check.svgY
  • Key:DZZWHBIBMUVIIW-DTORHVGOSA-N Yes check.svgY
   (verify)

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

Contents

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

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] [4] [5] [6]

Adverse reactions

Pharmacological properties

Sparfloxacin is about 37-45% bound to proteins in the blood. [11] [12]

Shimada et al. ( 1993) has summarized many of the studies published in Japanese regarding the tissue distribution of sparfloxacin. (high concentrations are achieved in sputum, pleural fluid, skin, lung, prostate, gynecological tissues, breast milk and otolaryngological tissues. *Salivary concentrations are 66 to 70% of plasma levels, while CSF penetration appears to be somewhat limited with CSF:plasma concentration ratios of only 0.25 to 0.35.

In rabbits, sparfloxacin achieves very good penetration into the ocular vitreous (54%), cornea (76%) and lens (36%). [17]

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.

See also

Related Research Articles

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References

  1. ↑ Psaty BM (December 2008). "Clinical trial design and selected drug safety issues for antibiotics used to treat community-acquired pneumonia". Clinical Infectious Diseases. 47 (Suppl 3): S176–S179. doi:10.1086/591400. PMC   2587028 . PMID   18986285.
  2. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 501. ISBN   9783527607495.
  3. 1 2 Rubinstein E (May 1996). "Safety profile of sparfloxacin in the treatment of respiratory tract infections". The Journal of Antimicrobial Chemotherapy. 37 (Suppl A): 145–160. doi: 10.1093/jac/37.suppl_a.145 . PMID   8737134.
  4. ↑ Goa KL, Bryson HM, Markham A (April 1997). "Sparfloxacin. A review of its antibacterial activity, pharmacokinetic properties, clinical efficacy and tolerability in lower respiratory tract infections". Drugs. 53 (4): 700–725. doi:10.2165/00003495-199753040-00010. PMID   9098667. S2CID   249883805.
  5. ↑ Stein GE, Havlichek DH (1997). "Sparfloxacin: potential clinical and economic impact in the treatment of respiratory infections". Pharmacotherapy. 17 (6): 1139–1147. doi:10.1002/j.1875-9114.1997.tb03079.x. PMID   9399598. S2CID   2652070.
  6. ↑ Zhanel GG, Ennis K, Vercaigne L, Walkty A, Gin AS, Embil J, et al. (2002). "A critical review of the fluoroquinolones: focus on respiratory infections". Drugs. 62 (1): 13–59. doi:10.2165/00003495-200262010-00002. PMID   11790155. S2CID   46961910.
  7. ↑ Bowie et al., 1989[ clarification needed ]
  8. ↑ Davey, 1989[ clarification needed ]
  9. ↑ Wolfson JS, Hooper DC (December 1991). "Overview of fluoroquinolone safety". The American Journal of Medicine. 91 (6A): 153S–161S. doi:10.1016/0002-9343(91)90330-z. PMID   1767803.
  10. ↑ Rubinstein E (May 1996). "Safety profile of sparfloxacin in the treatment of respiratory tract infections". The Journal of Antimicrobial Chemotherapy. 37 Suppl A: 145–160. doi: 10.1093/jac/37.suppl_a.145 . PMID   8737134.
  11. ↑ Shimada J, Nogita T, Ishibashi Y (November 1993). "Clinical pharmacokinetics of sparfloxacin". Clinical Pharmacokinetics. 25 (5): 358–369. doi:10.2165/00003088-199325050-00002. PMID   8287631. S2CID   30055898.
  12. ↑ Montay G (May 1996). "Pharmacokinetics of sparfloxacin in healthy volunteers and patients: a review". The Journal of Antimicrobial Chemotherapy. 37 Suppl A: 27–39. doi: 10.1093/jac/37.suppl_a.27 . PMID   8737123.
  13. ↑ Johnson JH, Cooper MA, Andrews JM, Wise R (November 1992). "Pharmacokinetics and inflammatory fluid penetration of sparfloxacin". Antimicrobial Agents and Chemotherapy. 36 (11): 2444–2446. doi:10.1128/aac.36.11.2444. PMC   284350 . PMID   1336947.
  14. ↑ Nogita T, Ishibashi Y (August 1991). "The penetration of sparfloxacin into human plasma and skin tissues". The Journal of Antimicrobial Chemotherapy. 28 (2): 313–314. doi:10.1093/jac/28.2.313. PMID   1663927.
  15. ↑ García I, Pascual A, Guzman MC, Perea EJ (May 1992). "Uptake and intracellular activity of sparfloxacin in human polymorphonuclear leukocytes and tissue culture cells". Antimicrobial Agents and Chemotherapy. 36 (5): 1053–1056. doi:10.1128/aac.36.5.1053. PMC   188834 . PMID   1324636.
  16. ↑ Wise R, Honeybourne D (May 1996). "A review of the penetration of sparfloxacin into the lower respiratory tract and sinuses". The Journal of Antimicrobial Chemotherapy. 37 Suppl A: 57–63. doi:10.1093/jac/37.suppl_a.57. PMID   8737125.
  17. ↑ Cochereau-Massin I, Bauchet J, Marrakchi-Benjaafar S, Saleh-Mghir A, Faurisson F, Vallois JM, et al. (April 1993). "Efficacy and ocular penetration of sparfloxacin in experimental streptococcal endophthalmitis". Antimicrobial Agents and Chemotherapy. 37 (4): 633–636. doi:10.1128/aac.37.4.633. PMC   187726 . PMID   8388193.
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