Nitisinone - CAS 104206-65-7
Catalog number: 104206-65-7
Category: Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
Molecular Weight:
Nitisinone(SC0735) is an inhibitor of the enzyme 4-hydroxyphenylpyruvate dioxygenase.
Canonical SMILES:
1.Inhibition of para-Hydroxyphenylpyruvate Dioxygenase by Analogues of the Herbicide Nitisinone As a Strategy to Decrease Homogentisic Acid Levels, the Causative Agent of Alkaptonuria.
Laschi M1, Bernardini G1, Dreassi E1, Millucci L1, Geminiani M1, Braconi D1, Marzocchi B1, Botta M1, Manetti F1, Santucci A2. ChemMedChem. 2016 Apr 5;11(7):674-8. doi: 10.1002/cmdc.201500578. Epub 2016 Mar 7.
Alkaptonuria (AKU) is a rare multisystem metabolic disease caused by deficient activity of homogentisate 1,2-dioxygenase (HGD), which leads to the accumulation of homogentisic acid (HGA). Currently, there is no treatment for AKU. The sole drug with some beneficial effects is the herbicide nitisinone (1), an inhibitor of p-hydroxyphenylpyruvate dioxygenase (4-HPPD). 1 has been used as a life-saving drug in infants with type I tyrosinemia despite severe side effects due to the buildup of tyrosine. Four clinical trials of nitisinone to treat AKU have shown that 1 consistently decreases HGA levels, but also caused the accumulation of tyrosine in blood serum. Moreover, the human preclinical toxicological data for 1 are incomplete. In this work, we performed pharmacodynamics and toxicological evaluations of 1, providing the first report of LD50 values in human cells. Intracellular tyrosinemia was also evaluated. Three additional 4-HPPD inhibitors with a more favorable profile than that of 1 in terms of IC50 , LD50 , and tyrosine accumulation were also identified among commercially available compounds.
2.Osteoarticular cells tolerate short-term exposure to nitisinone-implications in alkaptonuria.
Mistry JB1, Jackson DJ2, Bukhari M3, Taylor AM4. Clin Rheumatol. 2016 Feb;35(2):513-6. doi: 10.1007/s10067-015-2983-1. Epub 2015 May 31.
Alkaptonuria (AKU) is a rare genetic disease resulting in severe, rapidly progressing, early onset multi-joint osteoarthropathy. A potential therapy, nitisinone, is being trialled that reduces the causative agent; homogentisic acid (HGA) and in a murine model has shown to prevent ochronosis. Little is currently known about the effect nitisinone has on osteoarticular cells; these cells suffer most from the presence of HGA and its polymeric derivatives. This led us to investigate nitisinone's effect on chondrocytes and osteoblast-like cells in an in vitro model. Human C20/A4 immortalized chondrocytes, and osteosarcoma cells MG63 cultured in DMEM, as previously described. Confluent cells were then plated into 24-well plates at 4 × 10(4) cells per well in varying concentrations of nitisinone. Cells were cultured for 7 days with medium changes every third day. Trypan blue assay was used to determine viability and the effect of nitisinone concentration on cells.
3.Cost-Consequence Analysis of Nitisinone for Treatment of Tyrosinemia Type I.
Simoncelli M1, Samson J2, Bussières JF3, Lacroix J4, Dorais M5, Battista R6, Perreault S7. Can J Hosp Pharm. 2015 May-Jun;68(3):210-7.
in English, FrenchCONTEXTE: La tyrosinémie de type I est un trouble génétique du métabolisme rare, mais grave. La prise de nitisinone en association à un régime pauvre en tyrosine et en phénylalanine est devenue le traitement de première intention en 1994.
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CAS 104206-65-7 Nitisinone

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