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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015547
Secondary Accession Numbers
  • HMDB15547
Metabolite Identification
Common NameDeferasirox
DescriptionDeferasirox, also known as ICL 670 or exjade, 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. Deferasirox is a drug which is used for the treatment of chronic iron overload due to blood transfusions (transfusional hemosiderosis) in patients 2 years of age and older. Based on a literature review a significant number of articles have been published on Deferasirox.
Structure
Data?1582753309
Synonyms
ValueSource
DeferasiroxumChEBI
ExjadeChEBI
ICL 670ChEBI
ICL 670aChEBI
JadenuKegg
4-(3,5-Bis-(2-hydroxyphenyl)-(1,2,4)-triazol-1-yl)benzoic acidHMDB
ICL-670HMDB
ICL-670aHMDB
ICL670aHMDB
Chemical FormulaC21H15N3O4
Average Molecular Weight373.3615
Monoisotopic Molecular Weight373.106255983
IUPAC Name4-[bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid
Traditional Namedeferasirox
CAS Registry Number201530-41-8
SMILES
OC(=O)C1=CC=C(C=C1)N1N=C(N=C1C1=CC=CC=C1O)C1=CC=CC=C1O
InChI Identifier
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)
InChI KeyBOFQWVMAQOTZIW-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTriazoles
Direct ParentPhenyl-1,2,4-triazoles
Alternative Parents
Substituents
  • Phenyl-1,2,4-triazole
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point116 - 117 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.034 g/LNot Available
LogP3.52HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP4.01ALOGPS
logP4.74ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
pKa (Strongest Basic)0.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area108.47 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.32 m³·mol⁻¹ChemAxon
Polarizability38.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.81231661259
DarkChem[M-H]-184.99131661259
DeepCCS[M+H]+177.76430932474
DeepCCS[M-H]-175.40630932474
DeepCCS[M-2H]-209.47430932474
DeepCCS[M+Na]+184.59230932474
AllCCS[M+H]+187.032859911
AllCCS[M+H-H2O]+184.232859911
AllCCS[M+NH4]+189.632859911
AllCCS[M+Na]+190.432859911
AllCCS[M-H]-185.432859911
AllCCS[M+Na-2H]-184.432859911
AllCCS[M+HCOO]-183.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DeferasiroxOC(=O)C1=CC=C(C=C1)N1N=C(N=C1C1=CC=CC=C1O)C1=CC=CC=C1O5074.4Standard polar33892256
DeferasiroxOC(=O)C1=CC=C(C=C1)N1N=C(N=C1C1=CC=CC=C1O)C1=CC=CC=C1O3092.8Standard non polar33892256
DeferasiroxOC(=O)C1=CC=C(C=C1)N1N=C(N=C1C1=CC=CC=C1O)C1=CC=CC=C1O3485.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Deferasirox,1TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O)N=C2C2=CC=CC=C2O)C=C13718.9Semi standard non polar33892256
Deferasirox,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC=C1C1=NC(C2=CC=CC=C2O)=NN1C1=CC=C(C(=O)O)C=C13729.2Semi standard non polar33892256
Deferasirox,1TMS,isomer #3C[Si](C)(C)OC1=CC=CC=C1C1=NN(C2=CC=C(C(=O)O)C=C2)C(C2=CC=CC=C2O)=N13721.4Semi standard non polar33892256
Deferasirox,2TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O[Si](C)(C)C)N=C2C2=CC=CC=C2O)C=C13636.6Semi standard non polar33892256
Deferasirox,2TMS,isomer #2C[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O)N=C2C2=CC=CC=C2O[Si](C)(C)C)C=C13652.5Semi standard non polar33892256
Deferasirox,2TMS,isomer #3C[Si](C)(C)OC1=CC=CC=C1C1=NN(C2=CC=C(C(=O)O)C=C2)C(C2=CC=CC=C2O[Si](C)(C)C)=N13678.1Semi standard non polar33892256
Deferasirox,3TMS,isomer #1C[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O[Si](C)(C)C)N=C2C2=CC=CC=C2O[Si](C)(C)C)C=C13630.0Semi standard non polar33892256
Deferasirox,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O)N=C2C2=CC=CC=C2O)C=C13932.8Semi standard non polar33892256
Deferasirox,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C1=NC(C2=CC=CC=C2O)=NN1C1=CC=C(C(=O)O)C=C13968.5Semi standard non polar33892256
Deferasirox,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C1=NN(C2=CC=C(C(=O)O)C=C2)C(C2=CC=CC=C2O)=N13952.4Semi standard non polar33892256
Deferasirox,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O[Si](C)(C)C(C)(C)C)N=C2C2=CC=CC=C2O)C=C14039.8Semi standard non polar33892256
Deferasirox,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O)N=C2C2=CC=CC=C2O[Si](C)(C)C(C)(C)C)C=C14051.1Semi standard non polar33892256
Deferasirox,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC=C1C1=NN(C2=CC=C(C(=O)O)C=C2)C(C2=CC=CC=C2O[Si](C)(C)C(C)(C)C)=N14105.3Semi standard non polar33892256
Deferasirox,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(N2N=C(C3=CC=CC=C3O[Si](C)(C)C(C)(C)C)N=C2C2=CC=CC=C2O[Si](C)(C)C(C)(C)C)C=C14168.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Deferasirox GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-0249000000-473668bbd6515066ea8f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deferasirox GC-MS (3 TMS) - 70eV, Positivesplash10-0fk9-3203190000-0e9d49d98b2b8de164cb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Deferasirox GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , negative-QTOFsplash10-00fr-0009000000-e67e7fa4d17d7f182c352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , negative-QTOFsplash10-004i-0109000000-f5f73c7f47b72dfe17b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , negative-QTOFsplash10-0v0r-0964000000-dc562f553f7e4c323be02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , negative-QTOFsplash10-0gb9-0940000000-b177b6270b3dbb4ef6452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , negative-QTOFsplash10-014i-0910000000-bbc4de8399359b50ab8d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , negative-QTOFsplash10-014i-0900000000-639f8a3ca67f3974334e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , positive-QTOFsplash10-00di-0009000000-975b5b37a916fce72ae02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , positive-QTOFsplash10-00di-0009000000-bb3998f3d2229ff0647e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , positive-QTOFsplash10-00di-0119000000-e52c7bac508e519d74252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , positive-QTOFsplash10-0awc-2920000000-f025e2ec3e1b9ab199ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox LC-ESI-QFT , positive-QTOFsplash10-067i-4910000000-7092f8c0bcfae9c71d912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox , positive-QTOFsplash10-00di-0119000000-080e3290dbc4b90d8e2d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox 15V, Positive-QTOFsplash10-00di-0009000000-975b5b37a916fce72ae02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox 75V, Positive-QTOFsplash10-0awc-3920000000-d3ec2b3145148aed88ee2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox 45V, Positive-QTOFsplash10-00di-0109000000-e62b3b51001c76db3b802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox 45V, Negative-QTOFsplash10-0v0r-0964000000-3e343ab55c8e41ca7f0f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox 60V, Negative-QTOFsplash10-0gb9-0940000000-56cb21cde6472d904e802021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox 30V, Negative-QTOFsplash10-004i-0009000000-a5e8bc68cd181dffd68b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Deferasirox 15V, Negative-QTOFsplash10-00fr-0009000000-3035826e1dce820609c72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deferasirox 10V, Positive-QTOFsplash10-0ab9-0009000000-2c7a9307fa3d2088cc282016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deferasirox 20V, Positive-QTOFsplash10-0a6r-0009000000-7505e3377939d33704662016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deferasirox 40V, Positive-QTOFsplash10-0iki-4498000000-9da160ec5bd7e48629ef2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deferasirox 10V, Negative-QTOFsplash10-00di-0009000000-4618f43b17922ce02a6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deferasirox 20V, Negative-QTOFsplash10-00b9-0029000000-31b988ad2f12e767cf0d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Deferasirox 40V, Negative-QTOFsplash10-00di-3392000000-5e2ebcd60418ff652fe62016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01609 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01609 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01609
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10770206
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDeferasirox
METLIN IDNot Available
PubChem Compound214348
PDB IDNot Available
ChEBI ID49005
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase 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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
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. [PubMed:19940232 ]