Ciprofloksacin

Ciprofloxacin
1,4-dihydro-1-cyclopropyl-6-fluoro- 4-oxo-7-(1-piperazinyl)- 3-quinolinecarboxylic acid
CAS-nummer 85721-33-1	ATC-kode J01MA02, S01AX13, S03AA07
Kjemisk formel	C17H18FN3O3
Molekylvekt	331.345
Biotilgjengelighet	?
Metabolisme	?
Eliminasjons halveringstid	4 hours
Utskillelse	?
Graviditets kategori	2 (Legemiddelhåndboken)
Godkjenningsstatus	MT, Reseptpliktig gruppe C
Administrasjonsmåter	Oral, topisk (øredråper, øyedråper)

Ciprofloxacin er det generiske navn for et antibiotikum som produseres og markedsføres av Bayer Pharmaceutical under produktnavnet Ciproxin® (and other brand names in other markets, e.g. veterinary drugs), belonging to a group called fluoroquinolones. Ciprofloxacin is bactericidal and its mode of action depends on blocking of bacterial DNA replication by binding itself to an enzyme called DNA gyrase, which allows the untwisting required to replicate one DNA double helix into two. Notably the drug has 100 times higher affinity for bacterial DNA gyrase than for mammalian.

Ciprofloxacin er et bredspektret antibiotikum som er aktivt mot både Gram-positive og Gram-negative bakterier.

• Enterobacteriaceae
• Vibrio
• Hemophilus influenzae
• Neisseria gonorrhoeae
• Neisseria menigitidis
• Moraxella catarrhalis
• Brucella
• Campylobacter
• Mycobacterium intracellulare
• Legionella sp.
• Pseudomonas aeruginosa
• Bacillus anthracis som forårsaker miltbrann

Svak aktivitet mot:

• Streptococcus pneumoniae

Ingen aktivitet mot:

• Bacteroider
• Burkholderia cepacia
• Enterococcus faecium
• Ureaplasma urealyticum
• og andre

The major adverse effect seen with use of is gastrointestinal irritation, common with many antibiotics. Because of its general safety, potency and broad spectrum activity, ciprofloxacin was initially reserved as a 'last-resort' drug for use on difficult and drug-resistant infections. As with any antibiotic, however, increasing time and usage has led to an increase in ciprofloxacin-resistant infections, mainly in the hospital setting. Also implicated in the rise of resistant bacteria is the use of lower-cost, less potent fluoroquinolones, and the widespread addition of ciprofloxacin and other antibiotics to the feed of farm animals, which leads to greater and more rapid weight gain, for reasons which are not clear.

Label information

Ciprofloxacin er tilgjengelig i oral og parenteral formulering/bruk. C. blir brukt ved behandling av nedre luftveisinfeksjoner (lungebetennelse m.m.), urinveisinfeksjon, seksuelt overførbare sykdommer, sepsis, Legionærsyken og atypiske Mycobakterier.

C. er kontraindisert hos barn, ved gravidititet og ved epilepsi.

C. kan gi fotosensitivitets-reaksjoner og kan lede til forhøyet theofyllin-nivåer. Andre bivirkninger er obstipasjon og sensitivitet overfor koffein.

Business aspects

The discovery and development of ciprofloxacin is that rare case of an actual groundbreaking new drug development, opening up an entire new class of antibiotics for further research, development, and marketing. Even more remarkable, it seems to be a case where the first drug discovered of this class remains the 'gold standard' in terms of efficacy, with the other drugs developed by other pharmaceutical companies relegated to 'me-too' status and forced to compete on the basis of lower cost.

Encouraged by the magnitude of this success, as well as the influx of cash, Bayer Pharmaceutical embarked on a plan to remake itself from a minor pharmaceutical manufacturer into a major player in the international pharmaceutical business, with a lock on the antibiotic field. Unfortunately, a combination of the tendency for antibiotics to be viewed as a commodity and prescribed on the basis of lowest cost, Bayer's inability to follow up with another 'blockbuster' discovery, and a general downturn in the international pharmaceutical business forced Bayer into a major downsizing in 2000-2001. Faced with the imminent expiration of its patent rights to ciprofloxacin in the early 2000's and the predictable loss of market share to generic ciprofloxacin, Bayer has resorted to the usual strategy of pharmaceutical companies in such a situaton; focus on the development and patenting of new variations of the old drug (i.e. pediatric ciprofloxacin, intravenous ciprofloxacin, once-a-day ciprofloxacin, etc.), which will have the side effect of extending the patent on the original drug.

"Cipro" became a household word during the anthrax mail attacks after the destruction of the World Trade Center. Unfortunately, Bayer not only took a severe financial blow from the costs involved in rapidly increasing production of the drug to be sold to the government at far below market price, but ironically was then portrayed in the press as 'War Profiteers', rather than contributors to the safety of the public in the "War on Terror".