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SML0269

Nitisinone

Name: Nitisinone
Brand: SIGMA

≥95% (HPLC), 4-Hydroxyphenylpyruvate oxidase inhibitor, powder

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

UNSPSC Code:

12352200

PubChem Substance ID:

329825277

NACRES:

NA.77

MDL number:

MFCD01752192

Assay:

≥95% (HPLC)

Form:

powder

Quality level:

100

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Properties

Product Name

Nitisinone, ≥95% (HPLC)

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)

Description

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 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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000440923

0000092287

0000220952

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Increase of CSF tyrosine and impaired serotonin turnover in tyrosinemia type I.

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)

Experience of nitisinone for the pharmacological treatment of hereditary tyrosinaemia type 1.

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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Global Trade Item Number

SKU	GTIN
SML0269-10MG	04061837084010
SML0269-50MG	04061837084027