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SML0269

Sigma-Aldrich

Nitisinone

≥95% (HPLC)

Sinónimos:

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 (notación de Hill):
C14H10F3NO5
Número de CAS:
104206-65-7
Peso molecular:
329.23
MDL number:
MFCD01752192
UNSPSC Code:
12352200
PubChem Substance ID:
329825277
NACRES:
NA.77

Quality Level

100

assay

≥95% (HPLC)

form

powder

color

white to brown

solubility

DMSO: ≥5 mg/mL

storage temp.

−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

InChI key

OUBCNLGXQFSTLU-UHFFFAOYSA-N

Gene Information

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

Biochem/physiol Actions

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000092287
0000220952
0000198393
0000177132
0000177131

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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
Optimized HepaRG is a suitable cell source to generate the human liver chimeric mouse model for the chronic hepatitis B virus infection
Yuan L, et al.
Emerging microbes & infections, 7(1), 1-17 (2018)
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
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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