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SML0269

Sigma-Aldrich

Nitisinone

≥95% (HPLC)

Synonym(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

Empirical Formula (Hill Notation):
C14H10F3NO5
CAS Number:
104206-65-7
Molecular Weight:
329.23
MDL number:
MFCD01752192
UNSPSC Code:
12352200
PubChem Substance ID:
329825277
NACRES:
NA.77

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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)
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
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
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