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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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10 MG
R$ 893,00
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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

R$ 893,00

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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[1]
  • to treat Ixodes scapularis tick cells to inhibit the activity of hydroxyphenylpyruvate dioxygenase[2]
  • in supplemented water to block the accumulation of toxic metabolites in human hepatocyte engrafted mice[3]
  • to study its effect on bacterial pyomelanin production[4]

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
0000440923
0000440923
0000092287
0000092287
0000220952

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Jean Larochelle et al.
Molecular genetics and metabolism, 107(1-2), 49-54 (2012-08-14)
Hepatorenal tyrosinemia (HT1, fumarylacetoacetate hydrolase deficiency, MIM 276700) can cause severe hepatic, renal and peripheral nerve damage. In Québec, HT1 is frequent and neonatal HT1 screening is practiced. Nitisinone (NTBC, Orfadin ®) inhibits tyrosine degradation prior to the formation of
Pieter-Paul Schauwvlieghe et al.
Cornea, 32(1), 91-94 (2012-04-13)
To describe the confocal microscopic findings in a patient with hereditary tyrosinemia type I (HT-I) treated with 2-(2-nitro-4-trifluoromethylbenzoyl)-1,3-cyclohexanedione (NTBC) who developed corneal crystals. In this case study, we describe the confocal microscopic findings in a boy, who was diagnosed with
Andrew J Preston et al.
Annals of the rheumatic diseases, 73(1), 284-289 (2013-03-21)
Alkaptonuria (AKU) is a rare metabolic disease caused by deficiency of homogentisate 1,2 dioxygenase, an enzyme involved in tyrosine catabolism, resulting in increased circulating homogentisic acid (HGA). Over time HGA is progressively deposited as a polymer (termed ochronotic pigment) in
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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