Nitisinone

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Nitisinone
Struttura chimica del nitisinone
Struttura chimica del nitisinone
Nome IUPAC
2-[2-nitro-4-(trifluorometil)benzoil]
cicloesano-1,3-dione
Caratteristiche generali
Formula bruta o molecolareC14H10F3NO5
Massa molecolare (u)329.228 g/mol
Numero CAS104206-65-7
Numero EINECS691-056-0
Codice ATCA16AX04
PubChem115355
DrugBankDBDB00348
SMILES
O=C(c1ccc(cc1[N+]([O-])=O)C(F)(F)F)C2C(=O)CCCC2=O
Dati farmacologici
Modalità di
somministrazione		Orale
Dati farmacocinetici
Emivita54 h
Indicazioni di sicurezza
Modifica dati su Wikidata · Manuale

Il nitisinone (anche conosciuto come NTBC) è un farmaco, originariamente sviluppato come erbicida, utilizzato nel trattamento della tirosinemia di I tipo. A partire dal suo primo utilizzo con questa indicazione nel 1991, ha rimpiazzato il trapianto di fegato come terapia di prima linea per questa rara malattia[1]. È stato anche studiato come farmaco nel trattamento dell'alcaptonuria, una malattia correlata alla tirosinemia, ma meno grave[2].

È commercializzato come Orfadin[3].

Meccanismo d'azione

Il nitisinone agisce come inibitore reversibile dell'enzima 4-idrossifenilpiruvato ossidasi[4][5], riducendo la formazione di acido maleilacetoacetico e acido fumarilacetoacetico, i quali a loro volta possono essere convertiti in succinilacetone (SA), responsabile di danno al fegato e ai reni[1].

Sintesi del nitisinone

Note

  1. ^ a b McKiernan PJ, Nitisinone in the treatment of hereditary tyrosinaemia type 1, in Drugs, vol. 66, n. 6, 2006, pp. 743–50, DOI:10.2165/00003495-200666060-00002, PMID 16706549.
  2. ^ Phornphutkul C, Introne WJ, Perry MB, Isa Bernardini, Mark D. Murphey, Diana L. Fitzpatrick, Paul D. Anderson, Marjan Huizing e Yair Anikster, Natural history of alkaptonuria, in New England Journal Medicine, vol. 347, n. 26, 2002, pp. 2111–21, DOI:10.1056/NEJMoa021736, PMID 12501223. URL consultato il 13 aprile 2012 (archiviato dall'url originale il 5 gennaio 2010).
  3. ^ OrphaNet
  4. ^ Lock EA, Ellis MK, Gaskin P, Robinson M, Auton TR, Provan WM, Smith LL, Prisbylla MP, Mutter LC, Lee DL, From toxicological problem to therapeutic use: The discovery of the mode of action of 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione (NTBC), its toxicology and development as a drug, in Journal of Inherited Metabolic Disease, vol. 42, n. 21, 1998, pp. 498–506, DOI:10.1023/A:1005458703363, PMID 9728330.
  5. ^ Kavana M, Moran GR, Interaction of (4-hydroxyphenyl)pyruvate dioxygenase with the specific inhibitor 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione, in Biochemistry, vol. 42, n. 34, 2003, pp. 10238–45, DOI:10.1021/bi034658b, PMID 12939152.

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