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Merck

PHR1731

Supelco

Nitisinone

Pharmaceutical Secondary Standard; Certified Reference Material

Sinónimos:

Nitisinone, 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:
Peso molecular:
329.23
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

API family

nitisinone

CofA

current certificate can be downloaded

packaging

pkg of 1 g

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

-10 to -25°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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General description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards. Nitisinone is a medication, effectively used for the treatment and maintainence of alkaptonuria, an autosomal recessive disease. Its mode of action involves the inhibition of second enzyme in the tyrosine pathway, 4-hydroxyphenylpyruvate dioxygenase that produces HGA from 4-hydroxyphenylpyruvate.

Application

Nitisinone may be used as a pharmaceutical reference standard for the quantification of the analyte in phamraceutical formulations using high-performance liquid chromatography technique.
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

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.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAC0575 in the Documents slot below. This is an example certificate only and may not be the lot that you receive.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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Visite la Librería de documentos

Serum markers in alkaptonuria: simultaneous analysis of homogentisic acid, tyrosine and nitisinone by liquid chromatography tandem mass spectrometry
Hughes TA, et al.
Annals of Clinical Biochemistry, 52(5), 597-605 (2015)
Metabolic effects of increasing doses of nitisinone in the treatment of alkaptonuria
Gertsman I, et al.
JIMD Reports, 13(20), 57-57 (2015)
A stability indicating HPLC method for the determination of nitisinone in capsules
Souri E, et al.
Indian Journal of Pharmaceutical Sciences, 77(3), 348-348 (2015)
Shuzhang Yang et al.
Proceedings of the National Academy of Sciences of the United States of America, 116(44), 22229-22236 (2019-10-16)
Fumarylacetoacetate hydrolase (FAH) is the last enzyme in tyrosine catabolism, and mutations in the FAH gene are associated with hereditary tyrosinemia type I (HT1 or TYRSN1) in humans. In a behavioral screen of N-ethyl-N-nitrosourea mutagenized mice we identified a mutant

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