CAS No 201530-41-8 , 4-[(3Z,5E)-3,5-bis(6-oxocyclohexa-2,4-dien-1-ylidene)-1,2,
4-triazolidin-1-yl]benzoic acid

Title: Deferasirox
CAS Registry Number: 201530-41-8
CAS Name: 4-[3,5-Bis(2-hydroxyphenyl)-1H-1,2,4-triazol-1-yl]benzoic acid
Manufacturers' Codes: ICL-670; ICL-670A; CGP-72670
Trademarks: Exjade (Novartis)
Molecular Formula: C21H15N3O4
Molecular Weight: 373.36
Percent Composition: C 67.56%, H 4.05%, N 11.25%, O 17.14%
Literature References: Orally active tridentate iron chelator. Prepn: R. Lattmann, P. Acklin, WO 9749395; eidem, US 6465504 (1997, 2002 both to Novartis); U. Heinz et al., Angew. Chem. Int. Ed. 38, 2568 (1999). HPLC determn in plasma: M. C. Rouan et al., J. Chromatogr. B 755, 203 (2001). Iron complex formation study: S. Steinhauser et al., Eur. J. Inorg. Chem. 2004, 4177. Pharmacology: C. Hershko et al., Blood 97, 1115 (2001). Clinical pharmacokinetics: R. Galanello et al., J. Clin. Pharmacol. 43, 565 (2003). Clinical trial in thalassemia: E. Nisbet-Brown et al., Lancet 361, 1597 (2003). Review of structure activity: H. Nick et al., Curr. Med. Chem. 10, 1065-1076 (2003); of preclinical and clinical experience: M. D. Cappellini, Best Prac. Res. Clin. Haematol. 18, 289-298 (2005).
Properties: Crystals from ethanol, mp 264-265°. Soly in water at 25° (mg/ml): 0.4 (pH 7.40). pKa1 4.57, pKa2 8.71, pKa3 10.56 (Nick). Also reported in H2O/DMSO (CDMSO = 0.20) as pKa1 4.61, pKa2 10.12, pKa3 12.08 (Steinhauser). Partition coefficient (octanol/water): 6.3 (pH 7.40). uv max (H2O/DMSO, pH < 2): 284 nm (e 1.5 ′ 104).
Melting point: mp 264-265°
pKa: pKa1 4.57, pKa2 8.71, pKa3 10.56 (Nick); Also reported in H2O/DMSO (CDMSO = 0.20) as pKa1 4.61, pKa2 10.12, pKa3 12.08 (Steinhauser)
Log P: Partition coefficient (octanol/water): 6.3 (pH 7.40)
Absorption maximum: uv max (H2O/DMSO, pH < 2): 284 nm (e 1.5 ′ 104)
Therap-Cat: Chelating agent (iron).
Keywords: Chelating Agent.