- Accession Number
- Small Molecule
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.
- External IDs
- APO-066 / APO-66 / CP-20 / CP20 / DN-180-01-AF / L-1
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Ferriprox Tablet 1000 mg Oral Chiesi Canada Corp. 2015-04-28 Not applicable Ferriprox Solution 100 mg/1mL Oral ApoPharma USA, Inc. 2015-09-09 Not applicable Ferriprox Tablet, film coated 500 mg/1 Oral ApoPharma USA, Inc. 2011-11-25 Not applicable Ferriprox Tablet, film coated 1000 mg/1 Oral ApoPharma USA, Inc. 2019-08-01 Not applicable Ferriprox Tablet, film coated 1000 mg Oral Apotex Europe Bv 1999-08-25 Not applicable Ferriprox Tablet, film coated 1000 mg Oral Apotex Europe Bv 1999-08-25 Not applicable Ferriprox Tablet, film coated 1000 mg Oral Apotex Europe Bv 1999-08-25 Not applicable Ferriprox Solution 100 mg/ml Oral Apotex Europe Bv 1999-08-25 Not applicable Ferriprox Solution 100 mg/ml Oral Apotex Europe Bv 1999-08-25 Not applicable Ferriprox Tablet, film coated 500 mg Oral Apotex Europe Bv 1999-08-25 Not applicable
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Deferiprone Tablet 500 mg/1 Oral Taro Pharmaceuticals U.S.A., Inc. 2019-02-08 Not applicable
- CAS number
- Average: 139.1519
- Chemical Formula
- InChI Key
- IUPAC Name
Deferiprone is indicated in thalassemia syndromes when first line chelation agents are not adequate to treat transfusional iron overload.
- Associated Conditions
- 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.
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%.
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.
- Not Available
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
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.Learn more
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.Learn more
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.Learn more
- 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 Abacavir 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. Acetylcysteine zinc Acetylcysteine zinc can cause a decrease in the absorption of Deferiprone resulting in a reduced serum concentration and potentially a decrease 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.Additional Data Available
- Extended DescriptionExtended Description
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A severity rating for each drug interaction, from minor to major.Learn more
- Evidence LevelEvidence Level
A rating for the strength of the evidence supporting each drug interaction.Learn more
An effect category for each drug interaction. Know how this interaction affects the subject drug.Learn more
- Food Interactions
- Take with or without food. Food does not affect absorption.
- 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
- ATC Codes
- V03AC02 — Deferiprone
- AHFS Codes
- 64:00.00 — Heavy Metal Antagonists
- FDA label
- Download (287 KB)
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- Clinical Trials
- Not Available
- Not Available
- Dosage forms
Form Route Strength Tablet Oral 500 mg/1 Solution Oral 100 mg/1mL Solution Oral 100 mg/ml Solution Oral 100 mg Tablet Oral 1000 mg Tablet Oral 500 mg Tablet, film coated Oral 1000 mg Tablet, film coated Oral 1000 mg/1 Tablet, film coated Oral 500 mg/1 Tablet, film coated Oral 500 mg
- Not Available
Patent Number Pediatric Extension Approved Expires (estimated) US7049328 No 2006-05-23 2021-06-28 US8703156 No 2014-04-22 2029-10-29Additional Data Available
- Filed OnFiled On
The date on which a patent was filed with the relevant government.Learn more
- 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
- Mass Spec (NIST)
- Not Available
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
- 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.
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Pyridines and derivatives
- Sub Class
- Direct Parent
- Alternative Parents
- Hydroxypyridines / Dihydropyridines / Vinylogous amides / Heteroaromatic compounds / Cyclic ketones / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Dihydropyridine / Methylpyridine / Hydroxypyridine / Hydropyridine / Vinylogous amide / Heteroaromatic compound / Cyclic ketone / Azacycle / Organic nitrogen compound / Hydrocarbon derivative
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyridone (CHEBI:68554)
- Pharmacological action
- 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
- Uniprot ID
- Uniprot Name
- UDP-glucuronosyltransferase 1-6
- Molecular Weight
- 60750.215 Da
Drug created on December 28, 2012 12:38 / Updated on April 07, 2020 20:19