Grepafloxacina

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Grepafloxacina
Caratteristiche generali
Formula bruta o molecolareC19H22FN3O3
Massa molecolare (u)359.395 g/mol
Numero CAS119914-60-2
Numero EINECS631-454-3
Codice ATCJ01MA11
PubChem72474
DrugBankDBDB00365
SMILES
CC1CN(CCN1)C2=C(C(=C3C(=C2)N(C=C(C3=O)C(=O)O)C4CC4)C)F
Indicazioni di sicurezza
Modifica dati su Wikidata · Manuale

La grepafloxacina (nella fase sperimentale conosciuta anche con la sigla OPC-17116)[1] è un antibiotico che appartiene alla classe dei chinoloni[2] di terza generazione. Veniva solitamente impiegata nel trattamento delle infezioni delle vie urinarie e del tratto respiratorio. Sviluppata dalla società farmaceutica GlaxoSmithKline la grepafloxacina fu volontariamente ritirata dal commercio il 27 ottobre 1999,[3] quando in Italia risultava in commercio da sole due settimane,[4] per l'evidenza di un grave effetto indesiderato, cioè la tendenza a determinare un prolungamento dell'intervallo QT, spesso seguito da gravi e talvolta fatali aritmie.[5][6]

Farmacodinamica

La grepafloxacina, similmente ad altri chinoloni agisce tramite l'inibizione di due enzimi fondamentali per la cellula batterica, la DNA-girasi (conosciuta anche come topoisomerasi II) e la topoisomerasi IV. La DNA girasi è un enzima essenziale coinvolto nella replicazione, trascrizione e riparazione del DNA batterico. La topoisomerasi IV è invece un enzima che svolge un ruolo chiave nella partizione di batterico DNA cromosomico durante la divisione cellulare. Il blocco di questi meccanismi enzimatici porta alla morte del batterio.

Farmacocinetica

Dopo somministrazione orale la grepafloxacina viene rapidamente e ampiamente assorbita dal tratto gastrointestinale. La biodisponibilità del composto si aggira intorno al 70%. La concentrazione plasmatica massima (Cmax) viene raggiunta entro 2 o 3 ore dalla somministrazione. La contemporanea assunzione di cibo non sembra influenzare significativamente i parametri farmacocinetici. La molecola si distribuisce ampiamente nei fluidi e tessuti biologici, come dimostrato dall'ampio volume apparente di distribuzione (5,07 ± 0,95 l/kg). Il legame di grepafloxacina alle proteine plasmatiche umane è abbastanza basso (circa il 50%). L'antibiotico viene eliminato principalmente attraverso il metabolismo epatico e l'escrezione biliare. Solo una minima parte del chinolone (meno del 10% di una dose orale) viene eliminata immodificata nelle urine. La clearance orale della grepafloxacina risulta ridotta in soggetti con insufficienza epatica, pertanto il chinolone è controindicato per l'uso in questa popolazione di pazienti.

Usi clinici

La grepafloxacina trovava indicazione nelle riacutizzazioni di bronchite cronica causate da germi sensibili (ad esempio Haemophilus influenzae, Streptococcus pneumoniae, Moraxella catarrhalis),[7][8][9] nelle polmoniti acquisite in comunità (anche in quelle sostenute, oltre che dai precedenti germi, da Mycoplasma pneumoniae),[10][11][12] nella gonorrea e nelle uretriti e cerviciti non gonococciche, ad esempio causate da Chlamydia trachomatis o Ureaplasma urealyticum.[13][14]

Controindicazioni

La grepafloxacina è controindicata in soggetti con ipersensibilità nota al principio attivo, ad altri agenti antimicrobici nella classe dei chinoloni, oppure ad uno qualsiasi degli eccipienti utilizzati nella formulazione farmaceutica. Inoltre è controindicata nei pazienti con insufficienza epatica.

Stereochimica

Grepafloxacin contiene uno stereocentro e consiste di due enantiomeri. Si utilizza come racemo, cioè una miscela in rapporto 1:1 delle forme ( R ) e ( S ):

Enantiomeri di Grepafloxacin

CAS-Nummer: 146761-68-4
CAS-Nummer: 146761-69-5

Note

  1. ^ Neu HC, Fang W, Gu JW, Chin NX, In vitro activity of OPC-17116, in Antimicrob. Agents Chemother., vol. 36, n. 6, giugno 1992, pp. 1310–5, PMC 190337, PMID 1329620. URL consultato il 12 ottobre 2014.
  2. ^ Sasabe H, Kato Y, Suzuki T, Itose M, Miyamoto G, Sugiyama Y, Carrier-mediated uptake of grepafloxacin, a fluoroquinolone antibiotic, by the isolated rat lung cells, in Drug Metab. Pharmacokinet., vol. 20, n. 6, dicembre 2005, pp. 491–5, PMID 16415534. URL consultato il 12 ottobre 2014.
  3. ^ Glaxo Wellcome voluntarily withdraws Raxar (grepafloxacin) - 27/10/1999 (PDF), su fda.gov. URL consultato il 12 ottobre 2014.
  4. ^ Letter - Raxar, su fda.gov, FDA - U.S. Food and Drug Administation. URL consultato il 12 ottobre 2014.
  5. ^ Sprandel KA, Rodvold KA, Safety and tolerability of fluoroquinolones, in Clin Cornerstone, Suppl 3, 2003, pp. S29–36, PMID 14992418.
  6. ^ Stahlmann R, Lode H, Toxicity of quinolones, in Drugs, 58 Suppl 2, 1999, pp. 37–42, PMID 10553703.
  7. ^ Chodosh S, Lakshminarayan S, Swarz H, Breisch S, Efficacy and safety of a 10-day course of 400 or 600 milligrams of grepafloxacin once daily for treatment of acute bacterial exacerbations of chronic bronchitis: comparison with a 10-day course of 500 milligrams of ciprofloxacin twice daily, in Antimicrob. Agents Chemother., vol. 42, n. 1, gennaio 1998, pp. 114–20, PMC 105465, PMID 9449270. URL consultato il 12 ottobre 2014.
  8. ^ Langan CE, Cranfield R, Breisch S, Pettit R, Randomized, double-blind study of grepafloxacin versus amoxycillin in patients with acute bacterial exacerbations of chronic bronchitis, in J. Antimicrob. Chemother., 40 Suppl A, dicembre 1997, pp. 63–72, PMID 9484875. URL consultato il 12 ottobre 2014.
  9. ^ Langan CE, Zuck P, Vogel F, McIvor A, Peirzchala W, Smakal M, Staley H, Marr C, Randomized, double-blind study of short-course (5 day) grepafloxacin versus 10 day clarithromycin in patients with acute bacterial exacerbations of chronic bronchitis, in J. Antimicrob. Chemother., vol. 44, n. 4, ottobre 1999, pp. 515–23, PMID 10588313. URL consultato il 12 ottobre 2014.
  10. ^ O'Doherty B, Dutchman DA, Pettit R, Maroli A, Randomized, double-blind, comparative study of grepafloxacin and amoxycillin in the treatment of patients with community-acquired pneumonia, in J. Antimicrob. Chemother., 40 Suppl A, dicembre 1997, pp. 73–81, PMID 9484876. URL consultato il 12 ottobre 2014.
  11. ^ Felmingham D, Respiratory pathogens: assessing resistance patterns in Europe and the potential role of grepafloxacin as treatment of patients with infections caused by these organisms, in J. Antimicrob. Chemother., vol. 45, marzo 2000, pp. 1–8, PMID 10719006. URL consultato il 12 ottobre 2014.
  12. ^ Geddes AM., Grepafloxacin: an overview of antibacterial activity, pharmacokinetics, clinical efficacy and safety., in Expert Opin Investig Drugs., vol. 8, n. 4, aprile 1999, pp. 487-505, DOI:10.1517/13543784.8.4.487, PMID 15992094. URL consultato il 12 ottobre 2014.
  13. ^ Ridgway GL, Salman H, Robbins MJ, Dencer C, Felmingham D, The in-vitro activity of grepafloxacin against Chlamydia spp., Mycoplasma spp., Ureaplasma urealyticum and Legionella spp, in J. Antimicrob. Chemother., 40 Suppl A, dicembre 1997, pp. 31–4, PMID 9484871. URL consultato il 12 ottobre 2014.
  14. ^ McCormack WM, Martin DH, Hook EW, Jones RB, Daily oral grepafloxacin vs. twice daily oral doxycycline in the treatment of Chlamydia trachomatis endocervical infection, in Infect Dis Obstet Gynecol, vol. 6, n. 3, 1998, pp. 109–15, DOI:10.1155/S1064744998000210, PMC 1784789, PMID 9785106. URL consultato il 12 ottobre 2014.

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