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Details

Stereochemistry ACHIRAL
Molecular Formula C21H15N3O4
Molecular Weight 373.3615
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEFERASIROX

SMILES

OC(=O)C1=CC=C(C=C1)N2N=C(N=C2C3=CC=CC=C3O)C4=CC=CC=C4O

InChI

InChIKey=BOFQWVMAQOTZIW-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C21H15N3O4
Molecular Weight 373.3615
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Deferasirox (marketed as Exjade, Desirox, Deferasirox) is an iron chelator. Its main use is to reduce chronic iron overload in patients who are receiving long term blood transfusions for conditions such as beta-thalassemia and other chronic anemias. It is the first oral medication approved for this purpose in the USA by FDA in November 2005. It is approved in the European Union by the European Medicines Agency (EMA) for children 6 years and older for chronic iron overload from repeated blood transfusions. Deferasirox is highly selective for iron as Fe3+. In approximately 1-year clinical trials of patients with transfusional chronic iron overload associated with beta-thalassaemia, sickle cell disease, myelodysplastic syndrome or other rare chronic anaemias, deferasiroxhad a beneficial effect on liver iron concentrations (LIC) and serum ferritin levels. Deferasirox can cause acute renal failure, fatal in some patients and requiring dialysis in others. It was showed that most fatalities occurred in patients with multiple comorbidities in advanced stages of their hematological disorders.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
EXJADE
Secondary
EXJADE
PubMed

PubMed

TitleDatePubMed
A randomised comparison of deferasirox versus deferoxamine for the treatment of transfusional iron overload in sickle cell disease.
2007 Feb
Effects of deferasirox on renal function and renal epithelial cell death.
2011 Jun 10
Hypersensitivity reaction with deferasirox.
2015 Apr-Jun
Effects of deferasirox-deferoxamine on myocardial and liver iron in patients with severe transfusional iron overload.
2015 Jun 18
Patents

Sample Use Guides

In Vivo Use Guide
The recommended initial dose of Exjade (deferasitox) for patients 2 years of age and older is 20 mg per kg body weight orally, once daily. After commencing therapy, monitor serum ferritin monthly and adjust the dose of Exjade, if necessary, every 3-6 months based on serum ferritin trends. Make dose adjustments in steps of 5 or 10 mg per kg and tailor adjustments to the individual patient's response and therapeutic goals. In patients not adequately controlled with doses of 30 mg per kg (e.g., serum ferritin levels persistently above 2500 mcg/L and not showing a decreasing trend over time), doses of up to 40 mg per kg may be considered. Doses above 40 mg per kg are not recommended.
Route of Administration: Oral
In Vitro Use Guide
Cell proliferation was measured using the MTT assay after human DMS-53 small-cell lung carcinoma and SK-N-MC neuroepithelioma cells were treated with deferasirox for 72 hours at 37°C. Cellular growth assays demonstrated the antiproliferative activity of deferasirox against DMS-53 and SK-N-MC cell lines with IC50 values of12uM and 14uM respectively.
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:59:22 UTC 2019
Edited
by admin
on Mon Oct 21 21:59:22 UTC 2019
Record UNII
V8G4MOF2V9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEFERASIROX
EMA EPAR   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
4-(3,5-BIS(2-HYDROXYPHENYL)-1H-1,2,4-TRIAZOL-1-YL)BENZOIC ACID
Systematic Name English
BENZOIC ACID, 4-(3,5-BIS(2-HYDROXYPHENYL)-1H-1,2,4-TRIAZOL-1-YL)-
Common Name English
DEFERASIROX [VANDF]
Common Name English
ICL670A
Code English
OSVERAL
Brand Name English
ICL670
Code English
EXJADE
Brand Name English
DEFERASIROX [INN]
Common Name English
DEFERASIROX [USAN]
Common Name English
DEFERASIROX [EMA EPAR]
Common Name English
JADENU SPRINKLE
Brand Name English
DEFERASIROX [HSDB]
Common Name English
DEFERASIROX [MART.]
Common Name English
ICL-670A
Code English
JADENU
Brand Name English
DEFERASIROX [JAN]
Common Name English
DEFERASIROX [ORANGE BOOK]
Common Name English
DEFERASIROX [MI]
Common Name English
DEFERASIROX [WHO-DD]
Common Name English
ICL-670
Code English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS EXJADE (AUTHORIZED: BETA-THALASSEMIA)
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
FDA ORPHAN DRUG 161002
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
NDF-RT N0000000144
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
NCI_THESAURUS C62357
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
NDF-RT N0000175522
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
WHO-VATC QV03AC03
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
LIVERTOX 272
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
WHO-ATC V03AC03
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
FDA ORPHAN DRUG 354411
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
Code System Code Type Description
NDF-RT
N0000187062
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY Cytochrome P450 2C8 Inhibitors [MoA]
INN
8193
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
NDF-RT
N0000185506
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY Cytochrome P450 3A4 Inducers [MoA]
EVMPD
SUB21981
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
WIKIPEDIA
Deferasirox
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
EPA CompTox
201530-41-8
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
MERCK INDEX
M4131
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY Merck Index
MESH
C415250
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
LactMed
201530-41-8
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
EU-Orphan Drug
EU/3/02/092(EXPIRED)
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY Please note that this product was withdrawn from the Community Register of designated orphan medicinal products in September 2016 at the end of the period of market exclusivity. On 13 March 2002, orphan designation (EU/3/02/092) was granted by the European Commissin to Novartis Europharm Limited, United Kingdom, for 4-(3,5-bis-(hydroxy-phenyl)-1,2,4)triazol-1-yl)-benzoic acid for the treatment of chronic iron overload requiring chelation therapy.
NCI_THESAURUS
C48384
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
NDF-RT
N0000182138
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY Cytochrome P450 1A2 Inhibitors [MoA]
ChEMBL
CHEMBL550348
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
RXCUI
614373
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY RxNorm
CAS
201530-41-8
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
HSDB
201530-41-8
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
DRUG BANK
DB01609
Created by admin on Mon Oct 21 21:59:23 UTC 2019 , Edited by admin on Mon Oct 21 21:59:23 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
WEAK
IC50
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TARGET->LIGAND
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.
BINDING
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> INHIBITOR
WEAK
IC50
METABOLIC ENZYME -> SUBSTRATE
MINOR
Related Record Type Details
METABOLITE -> PARENT
PLASMA; URINE
METABOLITE -> PARENT
FECAL; URINE
METABOLITE -> PARENT
Presumably by CYP2D6
FECAL
METABOLITE -> PARENT
Presumably by CYP1A
FECAL
METABOLITE -> PARENT
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC