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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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10 MG
¥15,500
50 MG
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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

¥15,500

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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[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 Actions

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML0269-50MG:
SML0269-BULK:
SML0269-VAR:
SML0269-10MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000440923
0000440923
0000092287
0000092287
0000220952

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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)
Anne Davit-Spraul et al.
Journal of chromatographic science, 50(5), 446-449 (2012-04-19)
Tyrosinemia type 1, which is caused by a deficiency in fumarylacetoacetate hydrolase, is successfully treatable with nitisone (NTBC), an inhibitor of 4-hydroxyphenyl pyruvate dioxygenase. The recommended average dose of NTBC is 1 mg/kg per day. A rapid liquid chromatography (LC)
Eva Thimm et al.
Journal of inherited metabolic disease, 35(2), 263-268 (2011-11-10)
The implementation of NTBC into treatment of hypertyrosinemia type I (HT I) greatly improved survival by prevention of acute liver failure and hepatocellular carcinoma. However, there are first reports of cognitive impairment in patients with elevated plasma tyrosine concentrations. We
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