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SML0269

Sigma-Aldrich

Nitisinone

≥95% (HPLC)

Sinônimo(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

Fórmula empírica (Notação de Hill):
C14H10F3NO5
Número CAS:
104206-65-7
Peso molecular:
329.23
Número MDL:
MFCD01752192
Código UNSPSC:
12352200
ID de substância PubChem:
329825277
NACRES:
NA.77

Nível de qualidade

100

Ensaio

≥95% (HPLC)

Formulário

powder

cor

white to brown

solubilidade

DMSO: ≥5 mg/mL

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

OUBCNLGXQFSTLU-UHFFFAOYSA-N

Informações sobre genes

human ... HPD(3242)

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Aplicação

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

Ações bioquímicas/fisiológicas

Nitisinone is a competitive and reversible inhibitor of 4-Hydroxyphenylpyruvate oxidase (dioxygenase).
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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

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Certificados de análise (COA)

Lot/Batch Number
056M4712V
026M4776V
033M4733V
013M4721V
082M4713V

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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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