Deferiprone
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MedKoo CAT#: 314217

CAS#: 30652-11-0

Description: Deferiprone is a drug that chelates iron and is used to treat thalassaemia major. In 1994 was first approved for use in treating thalassaemia major in 1994 and had been licensed for use in Europe and Asia for many years while awaiting approval in Canada and the United States. On October 14, 2011, it was approved for use in the US under the FDAÂ’s accelerated approval program.

Chemical Structure

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Deferiprone
CAS# 30652-11-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 314217
Name: Deferiprone
CAS#: 30652-11-0
Chemical Formula: C7H9NO2
Exact Mass: 139.06
Molecular Weight: 139.150
Elemental Analysis: C, 60.42; H, 6.52; N, 10.07; O, 23.00

Price and Availability

Size Price Availability Quantity
1g USD 150
2g USD 250
5g USD 450 2 Weeks
10g USD 750 2 Weeks
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Synonym: Ferriprox

IUPAC/Chemical Name: 3-hydroxy-1,2-dimethylpyridin-4(1H)-one

InChi Key: TZXKOCQBRNJULO-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H9NO2/c1-5-7(10)6(9)3-4-8(5)2/h3-4,10H,1-2H3

SMILES Code: O=C1C(O)=C(C)N(C)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
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Biological target: Deferiprone is the only orally active iron-chelating drug to be used therapeutically in conditions of transfusional iron overload.
In vitro activity: It was hypothesized that DFP treatment could be used to selectively target mitochondria in cancer stem cells (CSCs). For this purpose, two ER(+) human breast cancer cell lines were used, namely MCF7 and T47D cells, as model systems. Figure 2A shows that DFP inhibits anchorage-independent growth remarkably well, with an IC-50 of ~100 nM for MCF7 cells and an IC-50 of ~500 nM for T47D cells after 5 days of treatment. Therefore, it was estimated that CSCs are approximately 1000-fold more sensitive to DFP than the “bulk” cancer cell population. In addition, CSCs’ formation was evaluated in the presence of NAC. Interestingly, it was observed that the DFP-induced reduction in the 3D tumorsphere formation reverted in the presence of 1 mM and 5 mM of NAC (Figure 2). Additionally, ALDH activity was used to further validate the effects of DFP on CSCs. Figure 3b demonstrates that 50 μM of DFP reduced the ALDH activity by >75% after 5 days of treatment. As ALDH is a metabolic marker of Epithelial-Mesenchymal Transition (EMT), this provides additional supporting evidence that DFP indeed targets the “stemness” phenotype of CSCs. Reference: Cells. 2020 Jun; 9(6): 1529. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7349387/
In vivo activity: The purpose of this study was to investigate the retinal-protective effects of the oral iron chelator deferiprone (DFP) in mice lacking the iron regulatory hormone hepcidin (Hepc). Hepc KO mice were given DFP in drinking water from age 6 to 18 months. They were then compared to Hepc KO mice not receiving DFP. In Hepc KO mice, DFP diminished RPE depigmentation and autofluorescence on fundus imaging. Autofluorescence in the RPE layer in cryosections was significantly diminished by DFP, consistent with the fundus images. Immunolabeling with L-ferritin and transferrin receptor antibodies showed a decreased signal for L-ferritin in the inner retina and RPE cells and an increased signal for transferrin receptor in the inner retina, indicating diminished retinal iron levels with DFP treatment. Plastic sections showed that photoreceptor and RPE cells were well preserved in Hepc KO mice treated with DFP. Consistent with photoreceptor protection, the mRNA level of rhodopsin was significantly higher in retinas treated with DFP. The mRNA levels of oxidative stress-related genes heme oxygenase-1 and catalase were significantly lower in DFP-treated Hepc KO retinas. Furthermore, ERG rod a- and b- and cone b-wave amplitudes were significantly higher in DFP-treated mice. Reference: Invest Ophthalmol Vis Sci. 2014 Jun 26;55(7):4525-32. https://pubmed.ncbi.nlm.nih.gov/24970260/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 7.1 51.31
H2O 18.0 129.36

Preparing Stock Solutions

The following data is based on the product molecular weight 139.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Fiorillo M, Tóth F, Brindisi M, Sotgia F, Lisanti MP. Deferiprone (DFP) Targets Cancer Stem Cell (CSC) Propagation by Inhibiting Mitochondrial Metabolism and Inducing ROS Production. Cells. 2020 Jun 23;9(6):1529. doi: 10.3390/cells9061529. PMID: 32585919; PMCID: PMC7349387. 2. Ramezanpour M, Smith JLP, Ooi ML, Gouzos M, Psaltis AJ, Wormald PJ, Vreugde S. Deferiprone has anti-inflammatory properties and reduces fibroblast migration in vitro. Sci Rep. 2019 Feb 20;9(1):2378. doi: 10.1038/s41598-019-38902-2. PMID: 30787349; PMCID: PMC6382764. 3. Carboni E, Tatenhorst L, Tönges L, Barski E, Dambeck V, Bähr M, Lingor P. Deferiprone Rescues Behavioral Deficits Induced by Mild Iron Exposure in a Mouse Model of Alpha-Synuclein Aggregation. Neuromolecular Med. 2017 Sep;19(2-3):309-321. doi: 10.1007/s12017-017-8447-9. Epub 2017 Jun 16. PMID: 28623611; PMCID: PMC5570801. 4. Song D, Zhao L, Li Y, Hadziahmetovic M, Song Y, Connelly J, Spino M, Dunaief JL. The oral iron chelator deferiprone protects against systemic iron overload-induced retinal degeneration in hepcidin knockout mice. Invest Ophthalmol Vis Sci. 2014 Jun 26;55(7):4525-32. doi: 10.1167/iovs.14-14568. PMID: 24970260; PMCID: PMC4106252.
In vitro protocol: 1. Fiorillo M, Tóth F, Brindisi M, Sotgia F, Lisanti MP. Deferiprone (DFP) Targets Cancer Stem Cell (CSC) Propagation by Inhibiting Mitochondrial Metabolism and Inducing ROS Production. Cells. 2020 Jun 23;9(6):1529. doi: 10.3390/cells9061529. PMID: 32585919; PMCID: PMC7349387. 2. Ramezanpour M, Smith JLP, Ooi ML, Gouzos M, Psaltis AJ, Wormald PJ, Vreugde S. Deferiprone has anti-inflammatory properties and reduces fibroblast migration in vitro. Sci Rep. 2019 Feb 20;9(1):2378. doi: 10.1038/s41598-019-38902-2. PMID: 30787349; PMCID: PMC6382764.
In vivo protocol: 1. Carboni E, Tatenhorst L, Tönges L, Barski E, Dambeck V, Bähr M, Lingor P. Deferiprone Rescues Behavioral Deficits Induced by Mild Iron Exposure in a Mouse Model of Alpha-Synuclein Aggregation. Neuromolecular Med. 2017 Sep;19(2-3):309-321. doi: 10.1007/s12017-017-8447-9. Epub 2017 Jun 16. PMID: 28623611; PMCID: PMC5570801. 2. Song D, Zhao L, Li Y, Hadziahmetovic M, Song Y, Connelly J, Spino M, Dunaief JL. The oral iron chelator deferiprone protects against systemic iron overload-induced retinal degeneration in hepcidin knockout mice. Invest Ophthalmol Vis Sci. 2014 Jun 26;55(7):4525-32. doi: 10.1167/iovs.14-14568. PMID: 24970260; PMCID: PMC4106252.

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1: Fisher SA, Brunskill SJ, Doree C, Chowdhury O, Gooding S, Roberts DJ. Oral deferiprone for iron chelation in people with thalassaemia. Cochrane Database Syst Rev. 2013 Aug 21;8:CD004839. doi: 10.1002/14651858.CD004839.pub3. Review. PubMed PMID: 23966105.

2: Pandolfo M, Hausmann L. Deferiprone for the treatment of Friedreich's ataxia. J Neurochem. 2013 Aug;126 Suppl 1:142-6. doi: 10.1111/jnc.12300. Review. PubMed PMID: 23859349.

3: Deferiprone (Ferriprox) for iron overload. Med Lett Drugs Ther. 2012 Feb 20;54(1384):15-6. Review. PubMed PMID: 22354281.

4: Pontikoglou C, Papadaki HA. Idiosyncratic drug-induced agranulocytosis: the paradigm of deferiprone. Hemoglobin. 2010 Jun;34(3):291-304. doi: 10.3109/03630269.2010.484791. Review. PubMed PMID: 20524819.

5: Cappellini MD, Musallam KM, Taher AT. Overview of iron chelation therapy with desferrioxamine and deferiprone. Hemoglobin. 2009;33 Suppl 1:S58-69. doi: 10.3109/03630260903346924. Review. PubMed PMID: 20001633.

6: Kontoghiorghes GJ. Prospects for introducing deferiprone as potent pharmaceutical antioxidant. Front Biosci (Elite Ed). 2009 Jun 1;1:161-78. Review. PubMed PMID: 19482634.

7: Vlachaki E, Tselios K, Perifanis V, Tsatra I, Tsayas I. Deferiprone-related arthropathy of the knee in a thalassemic patient: report of a case and review of the literature. Clin Rheumatol. 2008 Nov;27(11):1459-61. doi: 10.1007/s10067-008-0969-y. Epub 2008 Jul 29. Review. PubMed PMID: 18663554.

8: Kontoghiorghes GJ. Ethical issues and risk/benefit assessment of iron chelation therapy: advances with deferiprone/deferoxamine combinations and concerns about the safety, efficacy and costs of deferasirox. Hemoglobin. 2008;32(1-2):1-15. doi: 10.1080/03630260701726533. Review. PubMed PMID: 18274978.