4-[bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid

• ChemBase ID: 1386
• Molecular Formular: C21H15N3O4
• Molecular Mass: 373.3615
• Monoisotopic Mass: 373.10625598
• SMILES: n1c(nn(c1c1ccccc1O)c1ccc(cc1)C(=O)O)c1ccccc1O
• Canonical SMILES: OC(=O)c1ccc(cc1)n1nc(nc1c1ccccc1O)c1ccccc1O
• 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)
• InChIKey: BOFQWVMAQOTZIW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid
• IUPAC Traditional name: deferasirox; exjade
• Brand Name: Exjade
• Synonyms: 4-[3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic Acid; Deferasiroxum [inn-latin]; deferasirox; ICL 670; Deferasirox; Exjade; ICL-670; ICL-670A; CGP-72670

Database IDs

• CAS Number: 201530-41-8
• PubChem SID: 160964846; 46506791
• PubChem CID: 5493381

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.548632
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.7476976
• LogD (pH = 7.4): 1.9242212
• Log P: 4.744616
• Molar Refractivity: 125.3245 cm^3
• Polarizability: 40.60579 Å^3
• Polar Surface Area: 108.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.01
• LOG S: -4.04
• Solubility (Water): 3.43e-02 g/l

PROPERTIES

Physical Property

• Solubility: 0.038 mg/mL at 37 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; MeOH
• Apperance: White to Off-White Solid
• Melting Point: 260-262°C
• Hydrophobicity(logP): 3.52 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB01609

• Drug Groups: approved; investigational
• Description: Deferasirox is an oral 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 in the USA for this purpose.
• Indication: For the treatment of chronic iron overload due to blood transfusions (transfusional hemosiderosis) in patients 2 years of age and older.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: 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.
• Absorption: The absolute bioavailability (AUC) of deferasirox tablets for oral suspension is 70% compared to an intravenous dose.
• Half Life: The mean elimination half-life ranged from 8 to 16 hours following oral administration.
• Protein Binding: Deferasirox is highly (~99%) protein bound almost exclusively to serum albumin.
• 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).
• Distribution: * 14.37 ± 2.69 L
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1712

Research Area: Cardiovascular Disease
Biological Activity:
Deferasirox(Exjade) is a rationally-designed oral 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. The half-life of deferasirox is between 8 and 16 hours allowing once a day dosing. [1]

Toronto Research Chemicals - D228650

Orally active tridentate iron chelator.

REFERENCES

• http://en.wikipedia.org/wiki/Deferasirox
• Hershko, C., et al.: Blood, 97, 1115 (2001)
• Galanello, R., et al.: J. Clin. Pharmacol., 43, 565 (2001)
• Nick, H., et al.: Curr. Med. Chem., 10, 1065 (2001)