Nilotinib (AMN107; Tasigna)

Description: Nilotinib (formerly also known as AMN-107, AMN107; trade name Tasigna) is a potent, orally bioavailable aminopyrimidine-based Bcr-Abl inhibitor with antineoplastic activity. It inhibits Bcr-Abl with an IC50 of< 30 nM in Murine myeloid progenitor cells. As of 2007, nilotinib was approved by the US FDA for the treatment of imatinib-resistant chronic myelogenous leukemia which has the Philadelphia chromosome. Nilotinib was designed based on the structure of imatinib and showed the superiority over imatinib in newly diagnosed or imatinib-resistant chronic myelogenous leukemia (CML). It was more potent than imatinib to wild-type BCR-ABL in a wide range of CML-derived and transfected cell lines. Nilotinib was also efficacious in gastrointestinal stromal tumors.

References: Blood. 2007; 109(5):2112-20. Epub 2006 Oct 26; J Hepatol. 2011; 55(3):612-25; Cancer Cell. 2005; 7:129-41.

Related CAS #: 641571-10-0 (free base) 923288-90-8 (HCl hydrate) 923288-95-3(HCl)

Synonym: Nilotinib free base; AMN 107; AMN107; AMN-107; Nilotinib; US brand name: Tasigna.

Chemical Name: 4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)-3-{(4-(pyridin-3-yl)pyrimidin-2-yl)amino}benzamide

InChi Key: HHZIURLSWUIHRB-UHFFFAOYSA-N

InChi Code: InChI=1S/C28H22F3N7O/c1-17-5-6-19(10-25(17)37-27-33-9-7-24(36-27)20-4-3-8-32-14-20)26(39)35-22-11-21(28(29, 30)31)12-23(13-22)38-15-18(2)34-16-38/h3-16H, 1-2H3, (H, 35, 39)(H, 33, 36, 37)

SMILES Code: O=C(NC1=CC(C(F)(F)F)=CC(N2C=C(C)N=C2)=C1)C3=CC=C(C)C(NC4=NC=CC(C5=CC=CN=C5)=N4)=C3