alpelisib   Click here for help

GtoPdb Ligand ID: 7955

Synonyms: BYL 719 | BYL-719 | NVP-BYL719 | Piqray®
Approved drug PDB Ligand
alpelisib is an approved drug (FDA (2019), FDA (2020))
Compound class: Synthetic organic
Comment: Alpelisib is an orally bioavailable phosphatidylinositol 3-kinase (PI3K) inhibitor that exhibits antineoplastic activity. It is selective for the α isoform (PIK3CA). It was the first PIK3CA inhibitor to be approved for the treatment of breast cancer.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 129.45
Molecular weight 441.14
XLogP 1.82
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NC(=O)C1CCCN1C(=O)Nc1nc(c(s1)c1ccnc(c1)C(C(F)(F)F)(C)C)C
Isomeric SMILES NC(=O)[C@@H]1CCCN1C(=O)Nc1nc(c(s1)c1ccnc(c1)C(C(F)(F)F)(C)C)C
InChI InChI=1S/C19H22F3N5O2S/c1-10-14(11-6-7-24-13(9-11)18(2,3)19(20,21)22)30-16(25-10)26-17(29)27-8-4-5-12(27)15(23)28/h6-7,9,12H,4-5,8H2,1-3H3,(H2,23,28)(H,25,26,29)/t12-/m0/s1
InChI Key STUWGJZDJHPWGZ-LBPRGKRZSA-N
References
1. Furet P, Guagnano V, Fairhurst RA, Imbach-Weese P, Bruce I, Knapp M, Fritsch C, Blasco F, Blanz J, Aichholz R et al.. (2013)
Discovery of NVP-BYL719 a potent and selective phosphatidylinositol-3 kinase alpha inhibitor selected for clinical evaluation.
Bioorg Med Chem Lett, 23 (13): 3741-8. [PMID:23726034]
2. Lin S, Jin J, Liu Y, Tian H, Zhang Y, Fu R, Zhang J, Wang M, Du T, Ji M et al.. (2019)
Discovery of 4-Methylquinazoline Based PI3K Inhibitors for the Potential Treatment of Idiopathic Pulmonary Fibrosis.
J Med Chem, 62 (19): 8873-8879. [PMID:31335136]
3. Markham A. (2019)
Alpelisib: First Global Approval.
Drugs, 79 (11): 1249-1253. [PMID:31256368]
4. Venot Q, Blanc T, Rabia SH, Berteloot L, Ladraa S, Duong JP, Blanc E, Johnson SC, Hoguin C, Boccara O et al.. (2018)
Targeted therapy in patients with PIK3CA-related overgrowth syndrome.
Nature, 558 (7711): 540-546. [PMID:29899452]