Deferiprone
Identification
- Name
- Deferiprone
- Accession Number
- DB08826
- Description
Deferiprone is an oral iron chelator used as a second line agent in thalassemia syndromes when iron overload from blood transfusions occurs. Thalassemias are a type of hereditary anaemia due a defect in the production of hemoglobin. As a result, erythropoiesis, the production of new red blood cells, is impaired. FDA approved on October 14, 2011.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Deferiprone (DB08826)
- Weight
- Average: 139.1519
Monoisotopic: 139.063328537 - Chemical Formula
- C7H9NO2
- Synonyms
- 1,2-Dimethyl-3-hydroxypyrid-4-one
- 3-Hydroxy-1,2-dimethyl-4(1H)-pyridone
- Deferiprona
- Défériprone
- Deferiprone
- Deferipronum
- External IDs
- APO-066
- APO-66
- CP-20
- CP20
- DN-180-01-AF
- L-1
Pharmacology
- Indication
Deferiprone is indicated in thalassemia syndromes when first line chelation agents are not adequate to treat transfusional iron overload.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Deferiprone is an iron chelator that binds to ferric ions (iron III) and forms a 3:1 (deferiprone:iron) stable complex and is then eliminated in the urine. Deferiprone is more selective for iron in which other metals such as zinc, copper, and aluminum have a lower affinity for deferiprone.
- Absorption
Deferiprone is absorbed in the upper gastrointestinal tract. Absorption is rapid with maximum plasma concentrations occurring after 1 hour in the fasted state and after 2 hours in the fed state.
- Volume of distribution
In healthy patients, the volume of distribution is 1L/kg, and in thalassemia patients, the volume of distribution is 1.6L/kg.
- Protein binding
Plasma protein binding is less than 10%.
- Metabolism
Deferiprone is mainly metabolized by UGT1A6 to the 3-O-glucuronide metabolite. This metabolite cannot chelate iron.
- Route of elimination
Within 5-6 hours of administration, more than 90% of deferiprone is eliminated from the plasma. 75 to 90% of deferiprone is excreted in the urine as the metabolite.
- Half-life
The half-life is 1.9 hours.
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Agranulocytosis and neutropenia may occur, which can lead to fatal infections. Hepatoxicity is also possible. Most common side effects that lead to discontinuation of therapy were the gastrointestinal adverse effects (diarrhea, ulcer, nausea, gastrointestinal disturbances)
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbacavir Abacavir may decrease the excretion rate of Deferiprone which could result in a higher serum level. Acarbose Acarbose may decrease the excretion rate of Deferiprone which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Deferiprone which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Deferiprone which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Deferiprone which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Deferiprone which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Deferiprone which could result in a higher serum level. Aclidinium Deferiprone may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Deferiprone may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Deferiprone which could result in a higher serum level. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
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- Food Interactions
- Take with or without food. Food does not affect absorption.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataDeferiprone Lipomed Tablet, film coated Oral Lipomed 2018-09-19 Not applicable EU 
Ferriprox Tablet 1000 mg Oral Chiesi Canada Corp. 2015-04-28 Not applicable Canada 
Ferriprox Tablet, film coated 500 mg Oral Apotex Europe Bv 1999-08-25 Not applicable EU Ferriprox Solution 100 mg/1mL Oral ApoPharma USA, Inc. 2015-09-09 Not applicable US 
Ferriprox Tablet, film coated 1000 mg Oral Apotex Europe Bv 1999-08-25 Not applicable EU Ferriprox Solution 100 mg/ml Oral Apotex Europe Bv 1999-08-25 Not applicable EU Ferriprox Solution 100 mg Oral Chiesi Canada Corp. 2016-07-28 Not applicable Canada Ferriprox Tablet, film coated 500 mg/1 Oral ApoPharma USA, Inc. 2011-11-25 Not applicable US Ferriprox Tablet, film coated 1000 mg Oral Apotex Europe Bv 1999-08-25 Not applicable EU Ferriprox Solution 100 mg/ml Oral Apotex Europe Bv 1999-08-25 Not applicable EU Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataDeferiprone Tablet 500 mg/1 Oral Taro Pharmaceuticals U.S.A., Inc. 2019-02-08 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Categories
- ATC Codes
- V03AC02 — Deferiprone
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as methylpyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a methyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Methylpyridines
- Direct Parent
- Methylpyridines
- Alternative Parents
- Hydroxypyridines / Dihydropyridines / Vinylogous amides / Heteroaromatic compounds / Cyclic ketones / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Cyclic ketone / Dihydropyridine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyridine / Hydroxypyridine / Methylpyridine / Organic nitrogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyridone (CHEBI:68554)
Chemical Identifiers
- UNII
- 2BTY8KH53L
- CAS number
- 30652-11-0
- InChI Key
- TZXKOCQBRNJULO-UHFFFAOYSA-N
- InChI
- InChI=1S/C7H9NO2/c1-5-7(10)6(9)3-4-8(5)2/h3-4,10H,1-2H3
- IUPAC Name
- 3-hydroxy-1,2-dimethyl-1,4-dihydropyridin-4-one
- SMILES
- CN1C=CC(=O)C(O)=C1C
References
- General References
- Roberts DJ, Brunskill SJ, Doree C, Williams S, Howard J, Hyde CJ: Oral deferiprone for iron chelation in people with thalassaemia. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD004839. [PubMed:17636775]
- Victor Hoffbrand A: Deferiprone therapy for transfusional iron overload. Best Pract Res Clin Haematol. 2005 Jun;18(2):299-317. [PubMed:15737892]
- External Links
- KEGG Drug
- D07416
- PubChem Compound
- 2972
- PubChem Substance
- 175427107
- ChemSpider
- 2866
- 11645
- ChEBI
- 68554
- ChEMBL
- CHEMBL70927
- ZINC
- ZINC000000006226
- PharmGKB
- PA166118041
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Deferiprone
- AHFS Codes
- 64:00.00 — Heavy Metal Antagonists
- FDA label
- Download (287 KB)
- MSDS
- Download (76.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Acute iron intoxication / Beta Thalassemia Major Anemia 1 4 Completed Not Available Hepatic Impairment 1 4 Completed Not Available Impaired kidney function 1 4 Completed Treatment Acute iron intoxication / Cardiomyopathy 1 4 Completed Treatment Beta-Thalassemia / Thalassemia Major (TM) 1 4 Completed Treatment Hemosiderosis / Thalassemia Major (TM) 1 4 Completed Treatment Prolonged QT Interval 1 4 Enrolling by Invitation Treatment Acute iron intoxication / Other Anemias / Sickle Cell Disease (SCD) 1 4 Recruiting Treatment Acute iron intoxication / Other Anemias / Sickle Cell Disease (SCD) 1 4 Unknown Status Treatment Beta-Thalassemia 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 500 mg/1 Tablet, film coated Oral Solution Oral 100 mg/1mL Solution Oral 100 mg Solution Oral 100 mg/ml Tablet Oral 1000 mg/1 Tablet, film coated Oral 1000 mg/1 Tablet, film coated Oral 1000 mg Tablet, film coated Oral 500 mg Tablet, film coated Oral 500 mg/1 Syrup 100 mg/ml Tablet Oral 1000 mg Tablet, coated Oral 500 mg Tablet Oral 500 mg Capsule 250 mg Capsule 500 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS7049328 No 2006-05-23 2021-06-28 US US8703156 No 2014-04-22 2029-10-29 US US10780055 No 2018-10-25 2038-10-25 US Additional Data Available- Filed OnFiled OnAvailable for Purchase
The date on which a patent was filed with the relevant government.
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Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 272-278 Not Available water solubility Maximum water solubility of 16–18 g/L at 24° Not Available pKa 3.5 Not Available - Predicted Properties
Property Value Source Water Solubility 273.0 mg/mL ALOGPS logP -0.6 ALOGPS logP 0.61 ChemAxon logS 0.29 ALOGPS pKa (Strongest Acidic) 11.82 ChemAxon pKa (Strongest Basic) 0.52 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 40.54 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 40.7 m3·mol-1 ChemAxon Polarizability 14.05 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9803 Blood Brain Barrier + 0.9381 Caco-2 permeable + 0.8866 P-glycoprotein substrate Non-substrate 0.7895 P-glycoprotein inhibitor I Non-inhibitor 0.9143 P-glycoprotein inhibitor II Non-inhibitor 0.9156 Renal organic cation transporter Non-inhibitor 0.8293 CYP450 2C9 substrate Non-substrate 0.7463 CYP450 2D6 substrate Non-substrate 0.7407 CYP450 3A4 substrate Non-substrate 0.5587 CYP450 1A2 substrate Non-inhibitor 0.8281 CYP450 2C9 inhibitor Non-inhibitor 0.9871 CYP450 2D6 inhibitor Non-inhibitor 0.9504 CYP450 2C19 inhibitor Non-inhibitor 0.982 CYP450 3A4 inhibitor Non-inhibitor 0.9726 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9069 Ames test Non AMES toxic 0.7697 Carcinogenicity Non-carcinogens 0.9563 Biodegradation Ready biodegradable 0.5188 Rat acute toxicity 1.8734 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9539 hERG inhibition (predictor II) Non-inhibitor 0.8564
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Protein homodimerization activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 3 lacks trans...
- Gene Name
- UGT1A6
- Uniprot ID
- P19224
- Uniprot Name
- UDP-glucuronosyltransferase 1-6
- Molecular Weight
- 60750.215 Da
Drug created on December 28, 2012 12:38 / Updated on January 25, 2021 22:38