Gemifloxacin

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Gemifloxacin
Gemifloxacin.svg
Clinical data
Trade names Factive
AHFS/Drugs.com Monograph
MedlinePlus a604014
License data
Routes of
administration 		By mouth
ATC code
Legal status
Legal status
  • US: WARNING [1] Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 71%
Protein binding 60–70%
Metabolism Limited metabolism by the liver to minor metabolites
Excretion Feces (61%); urine (36%)
Identifiers
  • 7-[(4Z)-3-(Aminomethyl)-4-methoxyimino-pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-4-oxo- 1,8-naphthyridine-3-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H20FN5O4
Molar mass 389.387 g·mol−1
3D model (JSmol)
  • Fc2c(nc1N(/C=C(/C(=O)O)C(=O)c1c2)C3CC3)N4C/C(=N\OC)C(C4)CN
  • InChI=1S/C18H20FN5O4/c1-28-22-14-8-23(6-9(14)5-20)17-13(19)4-11-15(25)12(18(26)27)7-24(10-2-3-10)16(11)21-17/h4,7,9-10H,2-3,5-6,8,20H2,1H3,(H,26,27)/b22-14+ Yes check.svgY
  • Key:ZRCVYEYHRGVLOC-HYARGMPZSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Gemifloxacin mesylate, sold under the brand name Factive among others, is a broad-spectrum quinolone antibacterial agent used in the treatment of acute bacterial exacerbation of chronic bronchitis and mild-to-moderate pneumonia. It is taken by mouth. Vansen Pharma Inc. licensed the active ingredient from LG Life Sciences of Korea.[ citation needed ]

Contents

Indications

Gemifloxacin is indicated for the treatment of infections caused by susceptible strains of the designated microorganisms in the conditions listed below.

Microbiology

Gemifloxacin has been shown to be active against most strains of the following microorganisms:

Aerobic gram-positive microorganisms – Streptococcus pneumoniae [2]

including multi-drug resistant Streptococcus pneumoniae (MDRSP). MDRSP includes isolates previously known as PRSP (penicillin-resistant Streptococcus pneumoniae), and are strains resistant to two or more of the following antibiotics: penicillin, 2nd generation cephalosporins, e.g., cefuroxime, macrolides, tetracyclines and trimethoprim/sulfamethoxazole.

Staphylococcus aureus and Streptococcus pyogenes
Aerobic gram-negative microorganisms – Haemophilus influenzae , Haemophilus parainfluenzae , Klebsiella pneumoniae (many strains are moderately susceptible), Moraxella catarrhalis, Acinetobacter lwoffii , Klebsiella oxytoca , Legionella pneumophila , Proteus vulgaris .
Other microorganisms – Chlamydia pneumoniae , Mycoplasma pneumoniae

Adverse effects

Fluoroquinolones are generally well tolerated with most side effects being mild and serious adverse effects being rarely. [3] [4] Some of the serious adverse effects which occur more commonly with fluoroquinolones than with other antibiotic drug classes include CNS and tendon toxicity. [3] [5] The currently marketed quinolones have safety profiles similar to that of other antimicrobial classes. [3]

The serious events may occur with therapeutic or with acute overdose. At therapeutic doses they include: central nervous system toxicity, cardiovascular toxicity, tendon / articular toxicity, and rarely hepatic toxicity. [6] Events that may occur in acute overdose are rare and include: renal failure and seizure. [6] Children and the elderly are at greater risk. [3] [5] Tendon damage may manifest during, as well as up to a year after fluoroquinolone therapy. [7]

The FDA added a boxed warnings on all fluoroquinolones about the possible toxic effects of fluoroquinolones on tendons. [8]

In August 2013, the FDA issued a Safety Announcement where they described that they are requiring the medication guides and drug labels for all fluoroquinolones to be updated and better describe the risk for peripheral neuropathy. [9] The peripheral neuropathy may occur very quickly, and may be irreversible. This warning applies to fluoroquinolones taken by mouth and injection, but does not apply to fluoroquinolones taken topically.

Research

A study showed that gemifloxacin possess anti-metastatic activities against breast cancer in vitro and in vivo (in mice). [10]

Related Research Articles

<span class="mw-page-title-main">Ciprofloxacin</span> Fluoroquinolone antibiotic

Ciprofloxacin is a fluoroquinolone antibiotic used to treat a number of bacterial infections. This includes bone and joint infections, intra-abdominal infections, certain types of infectious diarrhea, respiratory tract infections, skin infections, typhoid fever, and urinary tract infections, among others. For some infections it is used in addition to other antibiotics. It can be taken by mouth, as eye drops, as ear drops, or intravenously.

<span class="mw-page-title-main">Levofloxacin</span> Antibiotic

Levofloxacin, sold under the brand name Levaquin among others, is a broad-spectrum antibiotic of the fluoroquinolone drug class. It is the left-handed isomer of the medication ofloxacin. It is used to treat a number of bacterial infections including acute bacterial sinusitis, pneumonia, H. pylori, urinary tract infections, Legionnaires' disease, chronic bacterial prostatitis, and some types of gastroenteritis. Along with other antibiotics it may be used to treat tuberculosis, meningitis, or pelvic inflammatory disease. It is available by mouth, intravenously, and in eye drop form.

<span class="mw-page-title-main">Bacterial pneumonia</span> Disease of the lungs

Bacterial pneumonia is a type of pneumonia caused by bacterial infection.

<span class="mw-page-title-main">Ofloxacin</span> Antibiotic to treat bacterial infections

Ofloxacin is a quinolone antibiotic useful for the treatment of a number of bacterial infections. When taken by mouth or injection into a vein, these include pneumonia, cellulitis, urinary tract infections, prostatitis, plague, and certain types of infectious diarrhea. Other uses, along with other medications, include treating multidrug resistant tuberculosis. An eye drop may be used for a superficial bacterial infection of the eye and an ear drop may be used for otitis media when a hole in the ear drum is present.

<span class="mw-page-title-main">Cefixime</span> A third generation cephalosporin antibiotic

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required. In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.

<span class="mw-page-title-main">Cefuroxime axetil</span> Chemical compound

Cefuroxime axetil, sold under the brand name Ceftin among others, is a second generation oral cephalosporin antibiotic.

Community-acquired pneumonia (CAP) refers to pneumonia contracted by a person outside of the healthcare system. In contrast, hospital-acquired pneumonia (HAP) is seen in patients who have recently visited a hospital or who live in long-term care facilities. CAP is common, affecting people of all ages, and its symptoms occur as a result of oxygen-absorbing areas of the lung (alveoli) filling with fluid. This inhibits lung function, causing dyspnea, fever, chest pains and cough.

<span class="mw-page-title-main">Moxifloxacin</span> Antibiotic

Moxifloxacin is an antibiotic, used to treat bacterial infections, including pneumonia, conjunctivitis, endocarditis, tuberculosis, and sinusitis. It can be given by mouth, by injection into a vein, and as an eye drop.

<span class="mw-page-title-main">Grepafloxacin</span> Chemical compound

Grepafloxacin was an oral broad-spectrum fluoroquinolone antibacterial agent used to treat bacterial infections. Grepafloxacin was withdrawn worldwide from markets in 1999, due to the drug's potential to cause a potentially fatal cardiac arrhythmia.

<span class="mw-page-title-main">Enrofloxacin</span> Chemical compound

Enrofloxacin, sold under the brand name Baytril, among others, is a fluoroquinolone antibiotic used for the treatment of animals. It is a bactericidal agent.

<span class="mw-page-title-main">Adenoiditis</span> Medical condition

Adenoiditis is the inflammation of the adenoid tissue usually caused by an infection. Adenoiditis is treated using medication or surgical intervention.

<span class="mw-page-title-main">Ceftibuten</span> Chemical to treat chronic bronchitis

Ceftibuten is a third-generation cephalosporin antibiotic. It is an orally administered agent, with two dosage forms, capsule or oral suspension. It is marketed by Pernix Therapeutics under the trade name Cedax.

<span class="mw-page-title-main">Cefditoren</span> Chemical to treat skin infections

Cefditoren, also known as cefditoren pivoxil is an antibiotic used to treat infections caused by Gram-positive and Gram-negative bacteria that are resistant to other antibiotics. It is mainly used for treatment of community acquired pneumonia. It is taken by mouth and is in the cephalosporin family of antibiotics, which is part of the broader beta-lactam group of antibiotics.

<span class="mw-page-title-main">Cefodizime</span> Chemical compound

Cefodizime is a 3rd generation cephalosporin antibiotic with broad spectrum activity against aerobic gram positive and gram negative bacteria. Clinically, it has been shown to be effective against upper and lower respiratory tract infections, urinary tract infections, and gonorrhea. Cefodizime is a bactericidal antibiotic that targets penicillin-binding proteins (PBPs) 1A/B, 2, and 3 resulting in the eventual death of the bacterial cell. In vivo experimental models of infection showed that bacterial clearance by this drug is at least as effective compared with other 3rd generation cephalosporins. It has similar adverse effect profile to other 3rd generation cephalosporins as well, mainly being limited to gastrointestinal or dermatological side effects.

<span class="mw-page-title-main">Delafloxacin</span> Chemical compound

Delafloxacin sold under the brand name Baxdela among others, is a fluoroquinolone antibiotic used to treat acute bacterial skin and skin structure infections.

<span class="mw-page-title-main">Acute exacerbation of chronic obstructive pulmonary disease</span> Medical condition

An acute exacerbation of chronic obstructive pulmonary disease, or acute exacerbations of chronic bronchitis (AECB), is a sudden worsening of chronic obstructive pulmonary disease (COPD) symptoms including shortness of breath, quantity and color of phlegm that typically lasts for several days.

<span class="mw-page-title-main">Quinolone antibiotic</span> Class of antibacterial drugs, subgroup of quinolones

Quinolone antibiotics constitute a large group of broad-spectrum bacteriocidals that share a bicyclic core structure related to the substance 4-quinolone. They are used in human and veterinary medicine to treat bacterial infections, as well as in animal husbandry, specifically poultry production.

<span class="mw-page-title-main">Zoliflodacin</span> Chemical compound

Zoliflodacin is an experimental antibiotic that is being studied for the treatment of infection with Neisseria gonorrhoeae (gonorrhea). It has a novel mechanism of action which involves inhibition of bacterial type II topoisomerases. Zoliflodacin is being developed by Innoviva Specialty Therapeutics, and the drug has demonstrated clinical efficacy equivalent to ceftriaxone in Phase III clinical trials.

<span class="mw-page-title-main">Levonadifloxacin</span> Chemical compound

Levonadifloxacin (trade name Emrok) is an antibiotic drug of the fluoroquinolone class. Chemically, it is the (S)-enantiomer of the racemic drug nadifloxacin.

References

  1. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  2. ↑ Calvo A, Gimenez MJ (2002). "Ex Vivo Serum Activity (Killing Rates) After Gemifloxacin 320 mg Versus Trovafloxacin 200 mg Single Doses Against Ciprofloxacin-Susceptible and -Resistant Streptococcus pneumoniae". Int. J. Antimicrob. Agents. 20 (2): 144–6. doi:10.1016/S0924-8579(02)00119-X. PMID   12297365.
  3. 1 2 3 4 Owens RC, Ambrose PG (July 2005). "Antimicrobial safety: focus on fluoroquinolones". Clinical Infectious Diseases. 41 (Suppl 2): S144–S157. doi: 10.1086/428055 . PMID   15942881.
  4. ↑ Ball P, Mandell L, Niki Y, Tillotson G (November 1999). "Comparative tolerability of the newer fluoroquinolone antibacterials". Drug Safety. 21 (5): 407–421. doi:10.2165/00002018-199921050-00005. PMID   10554054. S2CID   26842570.
  5. 1 2 Iannini PB (June 2007). "The safety profile of moxifloxacin and other fluoroquinolones in special patient populations". Current Medical Research and Opinion. 23 (6): 1403–1413. doi:10.1185/030079907X188099. PMID   17559736. S2CID   34091286.
  6. 1 2 Nelson LH, Flomenbaum N, Goldfrank LR, Hoffman RL, Howland MD, Lewin NA (2006). Goldfrank's toxicologic emergencies. New York: McGraw-Hill, Medical Pub. Division. ISBN   978-0-07-143763-9.
  7. ↑ Saint F, Gueguen G, Biserte J, Fontaine C, Mazeman E (September 2000). "[Rupture of the patellar ligament one month after treatment with fluoroquinolone]". Rev Chir Orthop Reparatrice Appar mot (in French). 86 (5): 495–7. PMID   10970974.
  8. ↑ "FDA orders 'black box' label on some antibiotics". CNN. 8 July 2008. Retrieved 8 July 2008.
  9. ↑ https://www.fda.gov/downloads/Drugs/DrugSafety/UCM365078.pdf [ bare URL PDF ]
  10. ↑ Chen TC (January 2014). "Gemifloxacin inhibits migration and invasion and induces mesenchymal-epithelial transition in human breast adenocarcinoma cells". J Mol Med (Berl). 92 (1): 53–64. doi:10.1007/s00109-013-1083-4. PMID   24005829. S2CID   11279701.
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