Deferiprone - CAS 30652-11-0
Catalog number: 30652-11-0
Category: Inhibitor
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A chelator that could replace disferrioxamine. It is orally and parenterally effective in the removal of iron in vivo from rabbits and mice and also from transferrin and ferritin in vitro.
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1.Longitudinal changes of endocrine and bone disease in adults with β-thalassemia major receiving different iron chelators over 5 years.
Poggi M1, Sorrentino F2, Pugliese P3, Smacchia MP4, Daniele C5, Equitani F6, Terlizzi F7, Guitarrini MR8, Monti S9, Maffei L2, Losardo A3, Pasin M5, Toscano V9. Ann Hematol. 2016 Apr;95(5):757-63. doi: 10.1007/s00277-016-2633-y. Epub 2016 Mar 9.
In this study, we compared the long-term effects of different iron chelation regimens (deferoxamine, deferiprone, deferoxamine + deferiprone, and deferasirox) in preventing or reversing endocrinopathy (diabetes mellitus, hypothyroidism, or hypogonadism) and bone disease (measured through DEXA) in 165 adults with β-thalassemia major (TM) (mean age 39.9 ± 8.3 years, 43 % males). After five consecutive years of therapy, patients on deferasirox had the highest decrease in the prevalence of any endocrinopathy compared to other chelators which either had no change (deferiprone and deferoxamine) or had an increase (deferoxamine + deferiprone), p = 0.015. This was attributed to a lower proportion of patients on deferasirox developing new-onset endocrinopathy and higher proportion showing reversal of disease, compared to other chelators. A serum ferritin level of >1300 ng/mL predicted the development of new endocrinopathy (p = 0.025) while a level of <200 ng/mL predicted reversal of existing endocrinopathy (p = 0.
2.Clinical Experience With Deferiprone Treatment for Friedreich Ataxia.
Elincx-Benizri S1, Glik A2, Merkel D3, Arad M4, Freimark D4, Kozlova E5, Cabantchik I6, Hassin-Baer S7. J Child Neurol. 2016 Mar 29. pii: 0883073816636087. [Epub ahead of print]
Friedreich ataxia is an inherited disorder characterized by degeneration of the peripheral and central nervous system and hypertrophic cardiomyopathy. Homozygous mutations in thefrataxine (FXN)gene reduce expression of frataxin and cause accumulation of iron in the mitochondria. Deferiprone, an oral iron chelator, has been shown effective in cell and animal models of Friedreich ataxia. The results of a 6-month randomized, double blind placebo-controlled study suggested that deferiprone 20 mg/kg/day may reduce disease progression. The authors present their experience of 5 Friedreich ataxia patients treated with deferiprone (20 mg/kg/day), in addition to idebenone treatment, followed over a period of 10-24 months, under off-label authorization. The patients were monitored for laboratory parameters, cardiac assessment, neurological evaluations, and quality of life. The authors conclude that combined therapy of a low dose of deferiprone with idebenone is relatively safe, might improve neurological function, and seems to improve heart hypertrophy, warranting further studies.
3.Systematic comparison of the mono-, dimethyl- and trimethyl 3-hydroxy-4(1H)-pyridones - Attempted optimization of the orally active iron chelator, deferiprone.
Xie YY1, Lu Z2, Kong XL2, Zhou T3, Bansal S2, Hider R4. Eur J Med Chem. 2016 Mar 5;115:132-140. doi: 10.1016/j.ejmech.2016.03.014. [Epub ahead of print]
A range of close analogues of deferiprone have been synthesised. The group includes mono-, di- and tri-methyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe3+ values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NH-containing hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues. As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis.
4.Hydroxypyridinones with enhanced iron chelating properties. Synthesis, characterization and in vivo tests of 5-hydroxy-2-(hydroxymethyl)pyridine-4(1H)-one.
Lachowicz JI1, Nurchi VM1, Crisponi G1, Jaraquemada-Pelaez MG1, Arca M1, Pintus A1, Santos MA2, Quintanova C2, Gano L3, Szewczuk Z4, Zoroddu MA5, Peana M5, Domínguez-Martín A6, Choquesillo-Lazarte D7. Dalton Trans. 2016 Apr 12;45(15):6517-28. doi: 10.1039/c6dt00129g.
The synthesis of 5-hydroxy-2-(hydroxymethyl)pyridin-4(1H)-one (P1) is presented, together with the evaluation of its coordination ability towards Fe(3+), studied by a combination of chemical, computational, and animal approaches. The use of complementary analytical techniques has allowed us to give evidence of the tautomeric changes of P1 as a function of pH, and to determine their influence on the coordinating ability of P1 towards Fe(3+). The pFe(3+) value 22.0 of P1-iron complexes is noticeably higher than that of deferiprone (20.6), one of the three clinical chelating agents in therapeutic use for iron overload diseases. This is due on one side to the tautomeric change to the catechol form, and on the other to the lower protonation constant of the OH group. Bio-distribution studies on mice allowed us to confirm in vivo the efficacy of P1. Furthermore the coordinating ability toward Al(3+), Cu(2+) and Zn(2+) has been studied to evaluate the possible use of P1 against a second toxic metal ion (Al(3+)), and to envisage its potential influence on the homeostatic equilibria of essential metal ions.
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CAS 30652-11-0 Deferiprone

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