BMS-599626   Click here for help

GtoPdb Ligand ID: 7647

Synonyms: AC1480 (free base) | AC480 | BMS 599626 | BMS599626
Compound class: Synthetic organic
Comment: BMS-599626 is an orally bioavailable inhibitor of the HER1, HER2 and HER4 tyrosine kinases. Note that some biocativity data may be assiociated with the hydrochloride salt AC-480 (PubChem CID 46930994).
This compound is being investigated as an antineoplastic agent [1-2].<
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 119.63
Molecular weight 530.22
XLogP 3.98
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(Nc1cn2c(c1C)c(ncn2)Nc1ccc2c(c1)cnn2Cc1cccc(c1)F)OCC1COCCN1
Isomeric SMILES O=C(Nc1cn2c(c1C)c(ncn2)Nc1ccc2c(c1)cnn2Cc1cccc(c1)F)OC[C@@H]1COCCN1
InChI InChI=1S/C27H27FN8O3/c1-17-23(34-27(37)39-15-22-14-38-8-7-29-22)13-36-25(17)26(30-16-32-36)33-21-5-6-24-19(10-21)11-31-35(24)12-18-3-2-4-20(28)9-18/h2-6,9-11,13,16,22,29H,7-8,12,14-15H2,1H3,(H,34,37)(H,30,32,33)/t22-/m0/s1
InChI Key LUJZZYWHBDHDQX-QFIPXVFZSA-N
References
1. Gavai AV, Fink BE, Fairfax DJ, Martin GS, Rossiter LM, Holst CL, Kim SH, Leavitt KJ, Mastalerz H, Han WC et al.. (2009)
Discovery and preclinical evaluation of [4-[[1-(3-fluorophenyl)methyl]-1H-indazol-5-ylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic acid, (3S)-3-morpholinylmethyl ester (BMS-599626), a selective and orally efficacious inhibitor of human epidermal growth factor receptor 1 and 2 kinases.
J. Med. Chem., 52 (21): 6527-30. [PMID:19821562]
2. Soria JC, Cortes J, Massard C, Armand JP, De Andreis D, Ropert S, Lopez E, Catteau A, James J, Marier JF et al.. (2012)
Phase I safety, pharmacokinetic and pharmacodynamic trial of BMS-599626 (AC480), an oral pan-HER receptor tyrosine kinase inhibitor, in patients with advanced solid tumors.
Ann. Oncol., 23 (2): 463-71. [PMID:21576284]