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SML0269

Sigma-Aldrich

Nitisinone

≥95% (HPLC)

Synonyme(s) :

2-(2-Nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione, 2-[2-Nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione, NTBC, Nitisone, SC 0735

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About This Item

Formule empirique (notation de Hill):
C14H10F3NO5
Numéro CAS:
104206-65-7
Poids moléculaire :
329.23
Numéro MDL:
MFCD01752192
Code UNSPSC :
12352200
ID de substance PubChem :
329825277
Nomenclature NACRES :
NA.77

Pureté

≥95% (HPLC)

Forme

powder

Couleur

white to brown

Solubilité

DMSO: ≥5 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

[O-][N+](=O)c1cc(ccc1C(=O)C2C(=O)CCCC2=O)C(F)(F)F

InChI

1S/C14H10F3NO5/c15-14(16,17)7-4-5-8(9(6-7)18(22)23)13(21)12-10(19)2-1-3-11(12)20/h4-6,12H,1-3H2

Clé InChI

OUBCNLGXQFSTLU-UHFFFAOYSA-N

Informations sur le gène

human ... HPD(3242)

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Application

Nitisinone has been used:
  • to induce liver injury
  • to treat Ixodes scapularis tick cells to inhibit the activity of hydroxyphenylpyruvate dioxygenase
  • in supplemented water to block the accumulation of toxic metabolites in human hepatocyte engrafted mice
  • to study its effect on bacterial pyomelanin production

Actions biochimiques/physiologiques

Nitisinone is a competitive inhibitor that reversibly inhibits 4-Hydroxyphenylpyruvate oxidase (dioxygenase). Nitisinone is used in the treatment of hereditary tyrosinemia type 1, where it blocks the degradation of tyrosine into harmful substances.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Methods to inhibit bacterial pyomelanin production and determine the corresponding increase in sensitivity to oxidative stress
Ketelboeter LM and Bardy SL
Journal of Visualized Experiments, (102), e53105-e53105 (2015)
Johannes Sander et al.
Clinica chimica acta; international journal of clinical chemistry, 412(1-2), 134-138 (2010-10-05)
Quantification of nitisinone, 2-(nitro-4-trifluoromethylbenzoyl)1,3-cyclohexanedione (NTBC) has been repeatedly described. Nevertheless monitoring of NTBC has not yet become part of routine therapy surveillance in tyrosinaemia type I (OMIM 276700). We developed a blood spot test to facilitate collection and transport of
Corinne de Laet et al.
Orphanet journal of rare diseases, 8, 8-8 (2013-01-15)
The management of tyrosinaemia type 1 (HT1, fumarylacetoacetase deficiency) has been revolutionised by the introduction of nitisinone but dietary treatment remains essential and the management is not easy. In this review detailed recommendations for the management are made based on
Eva Thimm et al.
Molecular genetics and metabolism, 102(2), 122-125 (2010-11-30)
Psychomotor impairment has been described in hypertyrosinemia types II and III (HT III). Only recently cognitive deficits have also been reported in hypertyrosinemia type I (HT I). The pathogenic mechanisms responsible are unknown. Since implementation of 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione (NTBC, Nitisinone (Swedish
Saikat Santra et al.
Expert opinion on pharmacotherapy, 9(7), 1229-1236 (2008-04-22)
Hereditary tyrosinaemia type 1 is a rare inherited metabolic condition, which leads to a fatal multisystemic disease in childhood. Since 1992, nitisinone - a compound developed from work on triketone herbicides - has become an effective pharmacological treatment by inhibiting
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