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SML0269

Sigma-Aldrich

Nitisinone

≥95% (HPLC)

Synonym(e):

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

Empirische Formel (Hill-System):
C14H10F3NO5
CAS-Nummer:
104206-65-7
Molekulargewicht:
329.23
MDL-Nummer:
MFCD01752192
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329825277
NACRES:
NA.77

Assay

≥95% (HPLC)

Form

powder

Farbe

white to brown

Löslichkeit

DMSO: ≥5 mg/mL

Lagertemp.

−20°C

SMILES String

[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

InChIKey

OUBCNLGXQFSTLU-UHFFFAOYSA-N

Angaben zum Gen

human ... HPD(3242)

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Anwendung

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

Biochem./physiol. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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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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