Deferasirox

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
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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofChronic iron overload••••••••••••••••• •••••••• ••••••• •••• ••• •••••• ••••••••••••••• ••••••••• •••••••••••• ••••• •••• ••••••••••••• •• •• ••••• • •• •• ••• •••• •• ••• ••••••
Treatment ofChronic iron overload••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

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.

TargetActionsOrganism
AIron
chelator
Humans
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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Toxicity

Not Available

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.
DrugInteraction
AbacavirThe metabolism of Abacavir can be decreased when combined with Deferasirox.
AbciximabThe risk or severity of gastrointestinal bleeding can be increased when Abciximab is combined with Deferasirox.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Deferasirox.
AcalabrutinibThe metabolism of Acalabrutinib can be increased when combined with Deferasirox.
AceclofenacThe 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

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Deferasirox (type J)Tablet180 mgOralJubilant Generics LimitedNot applicableNot applicableCanada flag
Deferasirox (type J)Tablet90 mgOralJubilant Generics LimitedNot applicableNot applicableCanada flag
Deferasirox (type J)Tablet360 mgOralJubilant Generics LimitedNot applicableNot applicableCanada flag
Deferasirox AccordTablet, film coated360 mgOralAccord Healthcare S.L.U.2020-12-16Not applicableEU flag
Deferasirox AccordTablet, film coated360 mgOralAccord Healthcare S.L.U.2020-12-16Not applicableEU flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-deferasiroxTablet, for suspension125 mgOralApotex Corporation2017-06-26Not applicableCanada flag
Apo-deferasiroxTablet, for suspension500 mgOralApotex Corporation2017-06-26Not applicableCanada flag
Apo-deferasiroxTablet, for suspension250 mgOralApotex Corporation2017-06-29Not applicableCanada flag
Apo-deferasirox (type J)Tablet360 mgOralApotex Corporation2019-05-29Not applicableCanada flag
Apo-deferasirox (type J)Tablet180 mgOralApotex Corporation2019-05-29Not applicableCanada flag

Categories

ATC Codes
V03AC03 — Deferasirox
Drug Categories
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
Human Metabolome Database
HMDB0015547
KEGG Drug
D03669
PubChem Compound
5493381
PubChem Substance
46506791
ChemSpider
10770206
BindingDB
50088376
RxNav
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

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Novartis AG
Dosage Forms
FormRouteStrength
Tablet, orally disintegratingOral
TabletOral180 mg/1
TabletOral250.000 mg
TabletOral360 mg/1
TabletOral90 mg/1
Tablet, coatedOral180 mg/1
Tablet, coatedOral360 mg/1
Tablet, coatedOral90 mg/1
Tablet, film coatedOral180 mg/1
Tablet, film coatedOral360 mg/1
Tablet, film coatedOral90 mg/1
Tablet, for suspensionOral125 mg/1
Tablet, for suspensionOral250 mg/1
Tablet, for suspensionOral500 mg/1
Tablet, solubleOral
Tablet, film coatedOral
Tablet, film coatedOral900 mg
Tablet, for suspensionOral125 MG
Tablet, for suspensionOral250 MG
Tablet, for suspensionOral500 MG
Tablet, film coatedOral180 MG
TabletOral125 mg
TabletOral250 mg
TabletOral
GranuleOral180 mg
GranuleOral360 mg
GranuleOral90 mg
TabletOral125.000 mg
Tablet, solubleOral125 mg
Tablet, solubleOral500 mg
Tablet, for suspensionOral125.0 mg
Tablet, for suspensionOral250.0 mg
Tablet, for suspensionOral500.0 mg
Tablet, for solutionOral125 mg
Tablet, for solutionOral250 mg
Tablet, for solutionOral500 mg
TabletOral250.00 mg
Tablet, orally disintegratingOral125 mg
Tablet, orally disintegratingOral250 mg
Tablet, orally disintegratingOral500 mg
GranuleOral180 mg/1
GranuleOral360 mg/1
GranuleOral90 mg/1
TabletOral180 mg
TabletOral360 mg
TabletOral90 mg
Tablet, coatedOral180 mg
Tablet, film coatedOral360 mg
Tablet, film coatedOral90 mg
Tablet, film coatedOral180.00 mg
Tablet, film coatedOral360.00 mg
Tablet, coatedOral360 mg
Tablet, coatedOral90 mg
TabletOral90.000 mg
Tablet, for suspensionOral
TabletOral500 mg
Tablet, solubleOral125.00 mg
TabletOral125.00 mg
Tablet, solubleOral250 mg
Prices
Unit descriptionCostUnit
Exjade 500 mg tablet78.61USD tablet
Exjade 250 mg tablet39.3USD tablet
Exjade 125 mg tablet19.65USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2255951No2006-10-102017-06-24Canada flag
US6596750No2003-07-222017-06-24US flag
US6465504No2002-10-152019-04-05US flag
US9283209No2016-03-152034-11-21US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)116-117 °CNot Available
water solubility0.038 mg/mL at 37 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.52HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0343 mg/mLALOGPS
logP4.01ALOGPS
logP4.74Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)4.51Chemaxon
pKa (Strongest Basic)-0.089Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area108.47 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity125.32 m3·mol-1Chemaxon
Polarizability38.52 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.993
Blood Brain Barrier+0.8508
Caco-2 permeable+0.5089
P-glycoprotein substrateNon-substrate0.7808
P-glycoprotein inhibitor INon-inhibitor0.894
P-glycoprotein inhibitor IINon-inhibitor0.8431
Renal organic cation transporterNon-inhibitor0.8708
CYP450 2C9 substrateNon-substrate0.7212
CYP450 2D6 substrateNon-substrate0.8686
CYP450 3A4 substrateNon-substrate0.6466
CYP450 1A2 substrateNon-inhibitor0.5802
CYP450 2C9 inhibitorNon-inhibitor0.7105
CYP450 2D6 inhibitorNon-inhibitor0.8221
CYP450 2C19 inhibitorNon-inhibitor0.5918
CYP450 3A4 inhibitorNon-inhibitor0.8179
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5717
Ames testNon AMES toxic0.6607
CarcinogenicityNon-carcinogens0.8519
BiodegradationNot ready biodegradable0.9524
Rat acute toxicity2.1119 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9684
hERG inhibition (predictor II)Non-inhibitor0.9072
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05fr-0249000000-473668bbd6515066ea8f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-00fr-0009000000-e67e7fa4d17d7f182c35
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0109000000-f5f73c7f47b72dfe17b4
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0v0r-0964000000-dc562f553f7e4c323be0
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0gb9-0940000000-b177b6270b3dbb4ef645
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0910000000-bbc4de8399359b50ab8d
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-014i-0900000000-639f8a3ca67f3974334e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0009000000-975b5b37a916fce72ae0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0009000000-bb3998f3d2229ff0647e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-0119000000-e52c7bac508e519d7425
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0awc-2920000000-f025e2ec3e1b9ab199ab
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-067i-4910000000-7092f8c0bcfae9c71d91
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0119000000-080e3290dbc4b90d8e2d
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-9f85f0e53788c7976d81
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-a42bd4fb4870d8659694
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-0009000000-351abb55f1e478645719
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0029000000-0edfbf4ff90295aea2a8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0009000000-082285ccbc68aa51ec7c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052b-0193000000-328a04d216965f2f7a31
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-205.2018312
predicted
DarkChem Lite v0.1.0
[M-H]-207.9029312
predicted
DarkChem Lite v0.1.0
[M-H]-175.4056
predicted
DeepCCS 1.0 (2019)
[M+H]+205.6671312
predicted
DarkChem Lite v0.1.0
[M+H]+208.1491312
predicted
DarkChem Lite v0.1.0
[M+H]+177.76358
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.6453312
predicted
DarkChem Lite v0.1.0
[M+Na]+207.9041312
predicted
DarkChem Lite v0.1.0
[M+Na]+184.59184
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Small molecule
Organism
Humans
Pharmacological action
Yes
Actions
Chelator
References
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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
Substrate
Inhibitor
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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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]
  2. Deferasirox FDA label [File]
  3. Exjade EMA label [File]

Drug created at August 29, 2007 19:21 / Updated at March 18, 2024 16:48