CHEBI:68554 - deferiprone

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ChEBI Name deferiprone
ChEBI ID CHEBI:68554
Definition A member of the class of 4-pyridones that is pyridin-4(1H)-one substituted at positions 1 and 2 by methyl groups and at position 3 by a hydroxy group. A lipid-soluble iron-chelator used for treatment of thalassaemia.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ChemicalBook:CB0308124, eMolecules:502935, Selleckchem:deferiprone, ZINC000000006226
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Deferiprone, sold under the brand name Ferriprox among others, is a medication that chelates iron and is used to treat iron overload in thalassaemia major. It was first approved and indicated for use in treating thalassaemia major in 1994 and had been licensed for use in the European Union for many years while awaiting approval in Canada and in the United States. On 14 October 2011, it was approved for use in the US under the FDA's accelerated approval program. The most common side effects include red-brown urine (showing that iron is being removed through the urine), nausea (feeling sick), abdominal pain (stomach ache) and vomiting. Less common but more serious side effects are agranulocytosis (very low levels of granulocytes, a type of white blood cell) and neutropenia (low levels of neutrophils, a type of white blood cell that fights infections).
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Formula C7H9NO2
Net Charge 0
Average Mass 139.15190
Monoisotopic Mass 139.06333
InChI InChI=1S/C7H9NO2/c1-5-7(10)6(9)3-4-8(5)2/h3-4,10H,1-2H3
InChIKey TZXKOCQBRNJULO-UHFFFAOYSA-N
SMILES Cc1c(O)c(=O)ccn1C
Roles Classification
Chemical Role(s): iron chelator

Application(s): protective agent
Synthetic or natural substance which is given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing deferiprone (CHEBI:68554) has role iron chelator (CHEBI:38157)
deferiprone (CHEBI:68554) has role protective agent (CHEBI:50267)
deferiprone (CHEBI:68554) is a 4-pyridones (CHEBI:20485)
IUPAC Name
3-hydroxy-1,2-dimethylpyridin-4(1H)-one
INN Source
deferiprone ChemIDplus
Synonyms Sources
1,2-Dimethyl-3-hydroxypyrid-4-one ChemIDplus
3-Hydroxy-1,2-dimethyl-4(1H)-pyridone ChemIDplus
Brand Name Source
Ferriprox KEGG DRUG
Manual Xrefs Databases
4188 DrugCentral
D07416 KEGG DRUG
Deferiprone Wikipedia
LSM-36972 LINCS
View more database links
Registry Numbers Types Sources
1447108 Reaxys Registry Number Reaxys
30652-11-0 CAS Registry Number KEGG DRUG
30652-11-0 CAS Registry Number ChemIDplus
Citations
Mohammadpour M, Behjati M, Sadeghi A, Fassihi A (2013)
Wound healing by topical application of antioxidant iron chelators: kojic acid and deferiprone.
International wound journal 10, 260-264 [PubMed:22621771]
[show Abstract]
Kolnagou A, Natsiopoulos K, Kleanthous M, Ioannou A, Kontoghiorghes GJ (2013)
Liver iron and serum ferritin levels are misleading for estimating cardiac, pancreatic, splenic and total body iron load in thalassemia patients: factors influencing the heterogenic distribution of excess storage iron in organs as identified by MRI T2*.
Toxicology mechanisms and methods 23, 48-56 [PubMed:22943064]
[show Abstract]
Rajapurkar MM, Hegde U, Bhattacharya A, Alam MG, Shah SV (2013)
Effect of deferiprone, an oral iron chelator, in diabetic and non-diabetic glomerular disease.
Toxicology mechanisms and methods 23, 5-10 [PubMed:22978744]
[show Abstract]
Maggio A, Vitrano A, Lucania G, Capra M, Cuccia L, Gagliardotto F, Pitrolo L, Prossomariti L, Filosa A, Caruso V, Gerardi C, Campisi S, Cianciulli P, Rizzo M, D'Ascola G, Ciancio A, Di Maggio R, Calvaruso G, Pantalone GR, Rigano P (2012)
Long-term use of deferiprone significantly enhances left-ventricular ejection function in thalassemia major patients.
American journal of hematology 87, 732-733 [PubMed:22622672]
[show Abstract]
Cassinerio E, Roghi A, Pedrotti P, Brevi F, Zanaboni L, Graziadei G, Pattoneri P, Milazzo A, Cappellini MD (2012)
Cardiac iron removal and functional cardiac improvement by different iron chelation regimens in thalassemia major patients.
Annals of hematology 91, 1443-1449 [PubMed:22572843]
[show Abstract]
Thompson MG, Corey BW, Si Y, Craft DW, Zurawski DV (2012)
Antibacterial activities of iron chelators against common nosocomial pathogens.
Antimicrobial agents and chemotherapy 56, 5419-5421 [PubMed:22850524]
[show Abstract]
Song TS, Hsieh YW, Peng CT, Liu CH, Chen TL, Hour MJ (2012)
Development of a fast LC-MS/MS assay for the determination of deferiprone in human plasma and application to pharmacokinetics.
Biomedical chromatography : BMC 26, 1575-1581 [PubMed:22457166]
[show Abstract]
Puglisi A, Spencer J, Oliveri V, Vecchio G, Kong X, Clarke J, Milton J (2012)
Synthesis, physicochemical properties and antioxidant activity of deferiprone-cyclodextrin conjugates and their iron(III) complexes.
Dalton transactions (Cambridge, England : 2003) 41, 2877-2883 [PubMed:22130677]
[show Abstract]
Song D, Song Y, Hadziahmetovic M, Zhong Y, Dunaief JL (2012)
Systemic administration of the iron chelator deferiprone protects against light-induced photoreceptor degeneration in the mouse retina.
Free radical biology & medicine 53, 64-71 [PubMed:22579919]
[show Abstract]
Aydinok Y, Evans P, Manz CY, Porter JB (2012)
Timed non-transferrin bound iron determinations probe the origin of chelatable iron pools during deferiprone regimens and predict chelation response.
Haematologica 97, 835-841 [PubMed:22180427]
[show Abstract]
Mirbehbahani N, Jahazi A, Rahim Abad HH (2012)
The effect of combined therapy with deferoxamine and deferiprone on serum ferritin level of beta-thalassemic patients.
Hematology (Amsterdam, Netherlands) 17, 183-186 [PubMed:22664119]
[show Abstract]
Šebestík J, Safařík M, Bouř P (2012)
Ferric complexes of 3-hydroxy-4-pyridinones characterized by density functional theory and Raman and UV-vis spectroscopies.
Inorganic chemistry 51, 4473-4481 [PubMed:22468647]
[show Abstract]
Prasanthi JR, Schrag M, Dasari B, Marwarha G, Dickson A, Kirsch WM, Ghribi O (2012)
Deferiprone reduces amyloid-β and tau phosphorylation levels but not reactive oxygen species generation in hippocampus of rabbits fed a cholesterol-enriched diet.
Journal of Alzheimer's disease : JAD 30, 167-182 [PubMed:22406440]
[show Abstract]
Alpendurada F, Smith GC, Carpenter JP, Nair SV, Tanner MA, Banya W, Dessi C, Galanello R, Walker JM, Pennell DJ (2012)
Effects of combined deferiprone with deferoxamine on right ventricular function in thalassaemia major.
Journal of cardiovascular magnetic resonance : official journal of the Society for Cardiovascular Magnetic Resonance 14, 8 [PubMed:22277065]
[show Abstract]
Sandmeier P, Clauss M, Donati OF, Chiers K, Kienzle E, Hatt JM (2012)
Use of deferiprone for the treatment of hepatic iron storage disease in three hornbills.
Journal of the American Veterinary Medical Association 240, 75-81 [PubMed:22171759]
[show Abstract]
Flaten TP, Aaseth J, Andersen O, Kontoghiorghes GJ (2012)
Iron mobilization using chelation and phlebotomy.
Journal of trace elements in medicine and biology : organ of the Society for Minerals and Trace Elements (GMS) 26, 127-130 [PubMed:22565013]
[show Abstract]
Manzoori JL, Amjadi M, Soleymani J, Tamizi E, Rezamand A, Jouyban A (2012)
Determination of deferiprone in urine and serum using a terbium-sensitized luminescence method.
Luminescence : the journal of biological and chemical luminescence 27, 268-273 [PubMed:21853518]
[show Abstract]
Prakash A, Aggarwal R (2012)
Thalassemia Major in Adults: Short Stature, Hyperpigmentation, Inadequate Chelation, and Transfusion-Transmitted Infections are Key Features.
North American journal of medical sciences 4, 141-144 [PubMed:22454828]
[show Abstract]
Abbas M, Nawaz R, Iqbal T, Alim M, Asi MR (2012)
Quantitative determination of deferiprone in human plasma by reverse phase high performance liquid chromatography and its application to pharmacokinetic study.
Pakistan journal of pharmaceutical sciences 25, 343-348 [PubMed:22459459]
[show Abstract]
Rodrat S, Yamanont P, Tankanitlert J, Chantraraksri U, Fucharoen S, Morales NP (2012)
Comparison of pharmacokinetics and urinary iron excretion of two single doses of deferiprone in β-thalassemia/hemoglobin E patients.
Pharmacology 90, 88-94 [PubMed:22759897]
[show Abstract]
Levy M, Llinas R (2012)
Pilot safety trial of deferiprone in 10 subjects with superficial siderosis.
Stroke 43, 120-124 [PubMed:22034002]
[show Abstract]
(2012)
Deferiprone (Ferriprox) for iron overload.
The Medical letter on drugs and therapeutics 54, 15-16 [PubMed:22354281]
Saljooghi AS (2012)
Chelation of aluminum by combining deferasirox and deferiprone in rats.
Toxicology and industrial health 28, 740-745 [PubMed:22025507]
[show Abstract]
Last Modified
22 February 2017