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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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107,00 €
50 MG
495,00 €

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Versandbereit am15. April 2025Details


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10 MG
107,00 €
50 MG
495,00 €

About This Item

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

107,00 €


Versandbereit am15. April 2025Details


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Qualitätsniveau

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[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]

Biochem./physiol. Wirkung

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable


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Die Dokumentenbibliothek aufrufen

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
Immunization with AgTRIO, a protein in Anopheles saliva, contributes to protection against Plasmodium infection in mice
Dragovic SM, et al.
Cell host & microbe, 23(4), 523-535 (2018)
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
Sairah Yousaf et al.
Pigment cell & melanoma research, 33(4), 556-565 (2020-04-11)
Skin pigmentation is a highly heterogeneous trait with diverse consequences worldwide. SLC24A5, encoding a potent K+ -dependent Na+ /Ca2+ exchanger, is among the known color-coding genes that participate in melanogenesis by maintaining pH in melanosomes. Deficient SLC24A5 activity results in

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