Compound: Ibrutinib
SMILES: O=C(N1C[C@H](n2nc(-c3ccc(Oc4ccccc4)cc3)c5c2ncnc5N)CCC1)C=C
InChIKey: XYFPWWZEPKGCCK-GOSISDBHSA-N
Synonyms: Ibrutinib, 936563-96-1, PCI-32765, IMBRUVICA, PCI 32765, CRA-032765, PCI32765, ibrutinibum, Pc-32765, 1X70OSD4VX, PCI-32765-00, CHEBI:76612, DTXSID60893450, 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one, 1-{(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}prop-2-en-1-one, 2-Propen-1-one, 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo(3,4-d)pyrimidin-1-yl)-1-piperidinyl)-, 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one, 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo(3,4-d)pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one, 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)pyrazolo(3,4-d)pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one, RefChem:57737, BTK Inhibitor PCI-32765, L01XE27, DTXCID601323465, 805-642-2, Ibrutinib (PCI-32765), (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one, MFCD20261150, 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one, PCI-32765 (Ibrutinib), C25H24N6O2, 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo(3,4-d)pyrimidin-1-yl)piperidin-1- yl)prop-2-en-1-one, Ibrutinib [USAN], Ibrutinib [USAN:INN], UNII-1X70OSD4VX, JNJ 02, Imbruvica (TN), 1-{(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1- yl}prop-2-en-1-one, Ibrutinib (Standard), CRA 032765, Ibrutinib, Free Base, IBRUTINIB [INN], IBRUTINIB [JAN], IBRUTINIB [MI], Ibrutinib (JAN/USAN), Ibrutinib Intermediate 2, IBRUTINIB [VANDF], IBRUTINIB [WHO-DD], Imbruvica; PCI-32765, MLS006010041, SCHEMBL201859, Ibrutinib - Bio-X trade mark, GTPL6912, orb1307353, orb3141322, PCI-32765 (Ibrutinib)?, IBRUTINIB [ORANGE BOOK], CHEMBL1873475, HSDB 8260, EX-A066, XYFPWWZEPKGCCK-GOSISDBHSA-N, GLXC-90098, BDBM50357312, EBC-11432, HY-10997R, NSC800769, AKOS022185476, DB09053, EX-5960, FA34130, NSC-800769, NCGC00187912-01, NCGC00187912-02, NCGC00187912-03, NCGC00187912-12, NCGC00187912-17, NCGC00187912-18, (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one., 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidyl]prop-2-en-1-one, AC-26942, BI164531, BP-43643, HY-10997, SMR004701213, NS00072153, SW218096-2, EN300-97039, D10223, F799864, A1-01649, Q5984881, BRD-K70301465-001-02-6, BRD-K70301465-001-05-9, Z1302446275, (R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-ylprop-2-en-1-one, 1-((R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one
Theoretical properties:
molecular_formula: C25H24N6O2
molecular_weight: 440.5 g/mol
exact_mass: 440.19607403 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 5
heavy_atom_count: 33
topological_polar_surface_area: 99.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white solid
color: White to off-white solid
melting_point: 149-158ºC
Descriptions:
pubchem: Ibrutinib is a member of the class of acrylamides that is (3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidine in which the piperidine nitrogen is replaced by an acryloyl group. A selective and covalent inhibitor of the enzyme Bruton's tyrosine kinase, it is used for treatment of B-cell malignancies. It has a role as an antineoplastic agent and an EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor. It is a tertiary carboxamide, a member of acrylamides, an aromatic amine, an aromatic ether, a pyrazolopyrimidine and a N-acylpiperidine.
chebi: A member of the class of acrylamides that is (3<i>R</i>)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-<em>d</em>]pyrimidin-1-yl]piperidine in which the piperidine nitrogen is replaced by an acryloyl group. A selective and covalent inhibitor of the enzyme Bruton's tyrosine kinase, it is used for treatment of B-cell malignancies.
wikipedia: Ibrutinib, sold under the brand name Imbruvica among others, is a small molecule drug that inhibits B-cell proliferation and survival by irreversibly binding the protein Bruton's tyrosine kinase (BTK). Blocking BTK inhibits the B-cell receptor pathway, which is often aberrantly active in B cell cancers. Ibrutinib is therefore used to treat such cancers, including mantle cell lymphoma, chronic lymphocytic leukemia, and Waldenström's macroglobulinemia. Ibrutinib also binds to C-terminal Src Kinases, which are off-target receptors for the BTK inhibitor. This binding inhibits the kinase from promoting cell differentiation and growth. Ibrutinib binds to these receptors and inhibits the kinase from promoting cell differentiation and growth. This leads to many different side effects like left atrial enlargement and atrial fibrillation during the treatment of Chronic Lymphocytic Leukemia.
It is on the World Health Organization's List of Essential Medicines.