Identification
- Summary
Deferasirox is an iron chelator used to treat chronic iron overload caused by blood transfusions. Also used in patients with non-transfusion-dependent thalassemia syndromes, and in patients with elevated liver iron concentration and serum ferritin.
- Brand Names
- Exjade, Jadenu
- Generic Name
- Deferasirox
- DrugBank Accession Number
- DB01609
- Background
Deferasirox is an iron chelator and the first oral medication FDA approved for chronic iron overload in patients receiving long term blood transfusions.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Deferasirox (DB01609)
- Weight
- Average: 373.3615
Monoisotopic: 373.106255983 - Chemical Formula
- C21H15N3O4
- Synonyms
- Deferasirox
- Deferasiroxum
- External IDs
- ICL 670
- ICL 670A
- ICL-670
- ICL-670A
- ICL670
- ICL670A
Pharmacology
- Indication
For the treatment of chronic iron overload due to blood transfusions (transfusional hemosiderosis) in patients 2 years of age and older.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Chronic iron overload •••••••••••• ••••• •••••••• ••••••• •••• ••• •••••• ••••••••••••••• ••••••••• •••••••••••• ••••• •••• ••••••••••••• •• •• ••••• • •• •• ••• •••• •• ••• •••••• Treatment of Chronic iron overload •••••••••••• - Contraindications & Blackbox Warnings
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Deferasirox is an orally active chelator that is selective for iron (as Fe3+). It is a tridentate ligand that binds iron with high affinity in a 2:1 ratio. Although deferasirox has very low affinity for zinc and copper there are variable decreases in the serum concentration of these trace metals after the administration of deferasirox. The clinical significance of these decreases is uncertain.
- Mechanism of action
Two molecules of deferasirox are capable of binding to 1 atom of iron. Deferasirox works in treating iron toxicity by binding trivalent (ferric) iron (for which it has a strong affinity), forming a stable complex which is eliminated via the kidneys.
Target Actions Organism AIron chelatorHumans - Absorption
The absolute bioavailability (AUC) of deferasirox tablets for oral suspension is 70% compared to an intravenous dose.
- Volume of distribution
- 14.37 ± 2.69 L
- Protein binding
Deferasirox is highly (~99%) protein bound almost exclusively to serum albumin.
- Metabolism
Hepatic. CYP450-catalyzed (oxidative) metabolism of deferasirox appears to be minor in humans (about 8%). Glucuronidation is the main metabolic pathway for deferasirox, with subsequent biliary excretion.
- Route of elimination
Deferasirox and metabolites are primarily (84% of the dose) excreted in the feces. Renal excretion of deferasirox and metabolites is minimal (8% of the administered dose).
- Half-life
The mean elimination half-life ranged from 8 to 16 hours following oral administration.
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Integrate drug-drug
interactions in your softwareAbacavir The metabolism of Abacavir can be decreased when combined with Deferasirox. Abciximab The risk or severity of gastrointestinal bleeding can be increased when Abciximab is combined with Deferasirox. Abemaciclib The metabolism of Abemaciclib can be increased when combined with Deferasirox. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Deferasirox. Aceclofenac The risk or severity of gastrointestinal bleeding and peptic ulcer can be increased when Aceclofenac is combined with Deferasirox. - Food Interactions
- Take at the same time every day.
- Take on an empty stomach. Take at least 30 minutes before food.
- Take separate from meals. Administration with food causes inconsistent bioavailability. May administer granules with a light meal, if necessary.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Deferasirox (type J) Tablet 360 mg Oral Jubilant Generics Limited Not applicable Not applicable Canada 
Deferasirox (type J) Tablet 180 mg Oral Jubilant Generics Limited Not applicable Not applicable Canada Deferasirox (type J) Tablet 90 mg Oral Jubilant Generics Limited Not applicable Not applicable Canada Deferasirox Accord Tablet, film coated 180 mg Oral Accord Healthcare S.L.U. 2020-12-16 Not applicable EU 
Deferasirox Accord Tablet, film coated 90 mg Oral Accord Healthcare S.L.U. 2020-12-16 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-deferasirox Tablet, for suspension 500 mg Oral Apotex Corporation 2017-06-26 Not applicable Canada Apo-deferasirox Tablet, for suspension 250 mg Oral Apotex Corporation 2017-06-29 Not applicable Canada Apo-deferasirox Tablet, for suspension 125 mg Oral Apotex Corporation 2017-06-26 Not applicable Canada Apo-deferasirox (type J) Tablet 90 mg Oral Apotex Corporation 2019-05-29 Not applicable Canada Apo-deferasirox (type J) Tablet 360 mg Oral Apotex Corporation 2019-05-29 Not applicable Canada
Categories
- ATC Codes
- V03AC03 — Deferasirox
- Drug Categories
- Acids, Carbocyclic
- Benzene Derivatives
- Benzoates
- Chelating Agents
- Compounds used in a research, industrial, or household setting
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Heavy Metal Antagonists
- Iron Chelating Activity
- Iron Chelating Agents
- Sequestering Agents
- Triazoles
- UGT1A1 Inhibitors
- UGT1A1 Substrates
- UGT1A3 Inhibitors
- UGT1A9 Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenyl-1,2,4-triazoles. These are organic compounds containing a 1,2,4-triazole substituted by a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Triazoles
- Direct Parent
- Phenyl-1,2,4-triazoles
- Alternative Parents
- Benzoic acids / Benzoyl derivatives / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds show 3 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Carboxylic acid / Carboxylic acid derivative show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- monocarboxylic acid, phenols, benzoic acids, triazoles (CHEBI:49005)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- V8G4MOF2V9
- CAS number
- 201530-41-8
- InChI Key
- BOFQWVMAQOTZIW-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H15N3O4/c25-17-7-3-1-5-15(17)19-22-20(16-6-2-4-8-18(16)26)24(23-19)14-11-9-13(10-12-14)21(27)28/h1-12,25-26H,(H,27,28)
- IUPAC Name
- 4-[3,5-bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid
- SMILES
- OC(=O)C1=CC=C(C=C1)N1N=C(N=C1C1=CC=CC=C1O)C1=CC=CC=C1O
References
- Synthesis Reference
Rajendra Suryabhan Patil, Kishore Charugundla, Praveen Kumar Neela, Nitin Sharadchandra Pradhan, Jon Valgeirsson, "SUBSTANTIALLY PURE DEFERASIROX AND PROCESSES FOR THE PREPARATION THEREOF." U.S. Patent US20110171138, issued July 14, 2011.
US20110171138- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015547
- KEGG Drug
- D03669
- PubChem Compound
- 5493381
- PubChem Substance
- 46506791
- ChemSpider
- 10770206
- BindingDB
- 50088376
- 614373
- ChEBI
- 49005
- ChEMBL
- CHEMBL550348
- ZINC
- ZINC000001481815
- PharmGKB
- PA164760843
- PDBe Ligand
- JBL
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Deferasirox
- PDB Entries
- 7erc
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Beta-Thalassemia Major / Hemosiderosis / Iron Overload / Rare Anemia 1 4 Completed Treatment Beta-Thalassemia / Myelodysplastic Syndrome 1 4 Completed Treatment Congenital Hypoplastic Anemia / Haemoglobinopathies congenital / MPD Syndrome / Myelodysplastic Syndrome / Other Inherited or Acquired Anaemia / Other Rare Anaemias / Transfusional Iron Overload 1 4 Completed Treatment Iron Overload 3 4 Completed Treatment Iron Overload After Hematopoietic Stem Cell Transplantation (HSCT) in Patients With Beta-thalassemia Major 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Novartis AG
- Dosage Forms
Form Route Strength Tablet, orally disintegrating Oral Tablet Oral 180 mg/1 Tablet Oral 250.000 mg Tablet Oral 360 mg/1 Tablet Oral 90 mg/1 Tablet, coated Oral 180 mg/1 Tablet, coated Oral 360 mg/1 Tablet, coated Oral 90 mg/1 Tablet, film coated Oral 180 mg/1 Tablet, film coated Oral 360 mg/1 Tablet, film coated Oral 90 mg/1 Tablet, for suspension Oral 125 mg/1 Tablet, for suspension Oral 250 mg/1 Tablet, for suspension Oral 500 mg/1 Tablet, soluble Oral Tablet, film coated Oral Tablet, film coated Oral 900 mg Tablet, for suspension Oral 125 MG Tablet, for suspension Oral 250 MG Tablet, for suspension Oral 500 MG Tablet, film coated Oral 180 MG Tablet Oral 125 mg Tablet Oral 250 mg Tablet Oral 500 mg Tablet Oral Granule Oral 180 mg Granule Oral 360 mg Granule Oral 90 mg Tablet Oral 125.000 mg Tablet, soluble Oral 125 mg Tablet, soluble Oral 500 mg Tablet, for suspension Oral 125.0 mg Tablet, for suspension Oral 250.0 mg Tablet, for suspension Oral 500.0 mg Tablet, for solution Oral 125 mg Tablet, for solution Oral 250 mg Tablet, for solution Oral 500 mg Tablet Oral 250.00 mg Tablet, orally disintegrating Oral 125 mg Tablet, orally disintegrating Oral 250 mg Tablet, orally disintegrating Oral 500 mg Granule Oral 180 mg/1 Granule Oral 360 mg/1 Granule Oral 90 mg/1 Tablet Oral 180 mg Tablet Oral 360 mg Tablet Oral 90 mg Tablet, coated Oral 180 mg Tablet, film coated Oral 360 mg Tablet, film coated Oral 90 mg Tablet, film coated Oral 180.00 mg Tablet, film coated Oral 360.00 mg Tablet, coated Oral 360 mg Tablet, coated Oral 90 mg Tablet Oral 90.000 mg Tablet, for suspension Oral Tablet, soluble Oral 125.00 mg Tablet Oral 125.00 mg Tablet, soluble Oral 250 mg - Prices
Unit description Cost Unit Exjade 500 mg tablet 78.61USD tablet Exjade 250 mg tablet 39.3USD tablet Exjade 125 mg tablet 19.65USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2255951 No 2006-10-10 2017-06-24 Canada US6596750 No 2003-07-22 2017-06-24 US 
US6465504 No 2002-10-15 2019-04-05 US US9283209 No 2016-03-15 2034-11-21 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 116-117 °C Not Available water solubility 0.038 mg/mL at 37 °C YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.52 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.0343 mg/mL ALOGPS logP 4.01 ALOGPS logP 4.74 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 4.51 Chemaxon pKa (Strongest Basic) -0.089 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 108.47 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 125.32 m3·mol-1 Chemaxon Polarizability 38.52 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.993 Blood Brain Barrier + 0.8508 Caco-2 permeable + 0.5089 P-glycoprotein substrate Non-substrate 0.7808 P-glycoprotein inhibitor I Non-inhibitor 0.894 P-glycoprotein inhibitor II Non-inhibitor 0.8431 Renal organic cation transporter Non-inhibitor 0.8708 CYP450 2C9 substrate Non-substrate 0.7212 CYP450 2D6 substrate Non-substrate 0.8686 CYP450 3A4 substrate Non-substrate 0.6466 CYP450 1A2 substrate Non-inhibitor 0.5802 CYP450 2C9 inhibitor Non-inhibitor 0.7105 CYP450 2D6 inhibitor Non-inhibitor 0.8221 CYP450 2C19 inhibitor Non-inhibitor 0.5918 CYP450 3A4 inhibitor Non-inhibitor 0.8179 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5717 Ames test Non AMES toxic 0.6607 Carcinogenicity Non-carcinogens 0.8519 Biodegradation Not ready biodegradable 0.9524 Rat acute toxicity 2.1119 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9684 hERG inhibition (predictor II) Non-inhibitor 0.9072
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 205.2018312 predictedDarkChem Lite v0.1.0 [M-H]- 207.9029312 predictedDarkChem Lite v0.1.0 [M-H]- 175.4056 predictedDeepCCS 1.0 (2019) [M+H]+ 205.6671312 predictedDarkChem Lite v0.1.0 [M+H]+ 208.1491312 predictedDarkChem Lite v0.1.0 [M+H]+ 177.76358 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.6453312 predictedDarkChem Lite v0.1.0 [M+Na]+ 207.9041312 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.59184 predictedDeepCCS 1.0 (2019)
Targets
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Yes
Chelator
References
- Wang T, Gao C, Chen BA: [Deferasirox--a new oral iron chelator--review]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2010 Oct;18(5):1359-64. [Article]
- Ibrahim AS, Spellberg B, Edwards J Jr: Iron acquisition: a novel perspective on mucormycosis pathogenesis and treatment. Curr Opin Infect Dis. 2008 Dec;21(6):620-5. doi: 10.1097/QCO.0b013e3283165fd1. [Article]
- Devanur LD, Evans RW, Evans PJ, Hider RC: Chelator-facilitated removal of iron from transferrin: relevance to combined chelation therapy. Biochem J. 2008 Jan 15;409(2):439-47. [Article]
- Lebitasy M, Ampe E, Hecq JD, Karmani L, Nick H, Galanti L: Ability of deferasirox to bind iron during measurement of iron. Clin Chem Lab Med. 2010 Mar;48(3):427-9. doi: 10.1515/CCLM.2010.080. [Article]
- Yang LP, Keam SJ, Keating GM: Deferasirox : a review of its use in the management of transfusional chronic iron overload. Drugs. 2007;67(15):2211-30. [Article]
- Choudhry VP, Naithani R: Current status of iron overload and chelation with deferasirox. Indian J Pediatr. 2007 Aug;74(8):759-64. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Skerjanec A, Wang J, Maren K, Rojkjaer L: Investigation of the pharmacokinetic interactions of deferasirox, a once-daily oral iron chelator, with midazolam, rifampin, and repaglinide in healthy volunteers. J Clin Pharmacol. 2010 Feb;50(2):205-13. doi: 10.1177/0091270009340418. Epub 2009 Nov 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Allegra S, De Francia S, Cusato J, Arduino A, Massano D, Longo F, Piga A, D'Avolio A: Deferasirox pharmacogenetic influence on pharmacokinetic, efficacy and toxicity in a cohort of pediatric patients. Pharmacogenomics. 2017 Apr;18(6):539-554. doi: 10.2217/pgs-2016-0176. Epub 2017 Mar 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
References
- Allegra S, De Francia S, Cusato J, Arduino A, Massano D, Longo F, Piga A, D'Avolio A: Deferasirox pharmacogenetic influence on pharmacokinetic, efficacy and toxicity in a cohort of pediatric patients. Pharmacogenomics. 2017 Apr;18(6):539-554. doi: 10.2217/pgs-2016-0176. Epub 2017 Mar 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Retinoic acid binding
- 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 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- Nakajima M, Yamanaka H, Fujiwara R, Katoh M, Yokoi T: Stereoselective glucuronidation of 5-(4'-hydroxyphenyl)-5-phenylhydantoin by human UDP-glucuronosyltransferase (UGT) 1A1, UGT1A9, and UGT2B15: effects of UGT-UGT interactions. Drug Metab Dispos. 2007 Sep;35(9):1679-86. doi: 10.1124/dmd.107.015909. Epub 2007 Jun 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Waldmeier F, Bruin GJ, Glaenzel U, Hazell K, Sechaud R, Warrington S, Porter JB: Pharmacokinetics, metabolism, and disposition of deferasirox in beta-thalassemic patients with transfusion-dependent iron overload who are at pharmacokinetic steady state. Drug Metab Dispos. 2010 May;38(5):808-16. doi: 10.1124/dmd.109.030833. Epub 2010 Jan 22. [Article]
- Deferasirox FDA label [File]
- Exjade EMA label [File]
Drug created at August 29, 2007 19:21 / Updated at February 20, 2024 23:55