1E8

1-{(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}prop-2-en-1-one



Chemical Component Summary

Name1-{(3R)-3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl}prop-2-en-1-one
SynonymsImbruvica; PCI-32765
Identifiers1-[(3R)-3-[4-azanyl-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
FormulaC25 H24 N6 O2
Molecular Weight440.497
TypeNON-POLYMER
Isomeric SMILESC=CC(=O)N1CCC[C@H](C1)n2c3c(c(n2)c4ccc(cc4)Oc5ccccc5)c(ncn3)N
InChIInChI=1S/C25H24N6O2/c1-2-21(32)30-14-6-7-18(15-30)31-25-22(24(26)27-16-28-25)23(29-31)17-10-12-20(13-11-17)33-19-8-4-3-5-9-19/h2-5,8-13,16,18H,1,6-7,14-15H2,(H2,26,27,28)/t18-/m1/s1
InChIKeyXYFPWWZEPKGCCK-GOSISDBHSA-N

Chemical Details

Formal Charge0
Atom Count57
Chiral Atom Count1
Bond Count61
Aromatic Bond Count22

Drug Info: DrugBank

DrugBank IDDB09053 
NameIbrutinib
Groups approved
DescriptionIbrutinib is a small molecule that acts as an irreversible potent inhibitor of Burton's tyrosine kinase. It is designated as a targeted covalent drug and presented as a promising activity in B-cell malignancies in clinical trials.[A32299] Ibrutinib was developed by Pharmacyclics Inc and was first approved by the FDA in November 2013 for the treatment of mantle cell lymphoma (MCL) under accelerated approval;[L12228] however, in April 2023, the drug manufacturer withdrew the accelerated approvals for ibrutinib in the US.[L45894] Ibrutinib was approved by the EMA in October 2014 [L45884] and by Health Canada in November 2014.[L45889] It is currently approved for the treatment of various conditions, such as chronic lymphocytic leukemia (CLL), Waldenström's Macroglobulinemia, and chronic graft versus host disease (cGVHD) in August 2017.[L12228] Notably, ibrutinib became the first FDA-approved cGVHD treatment for children in August 2017.[L43020]
Synonyms
  • Ibrutinib
  • 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
Brand NamesImbruvica
IndicationIbrutinib is indicated for the treatment of the following conditions. **Chronic lymphocytic leukemia (CLL)/small lymphocytic lymphoma (SLL)** - In the US, it is used in adult patients with or without 17p deletion.[L42980, L45884] - In Europe and Canada, it is used as a single agent or combined with [rituximab], [obinutuzumab], or [venetoclax] in previously untreated CLL patients. In patients who have received at least one prior therapy, it is used as a single agent or in combination with [bendamustine] and [rituximab].[L45884, L45889] **Waldenström's macroglobulinemia** - It is used alone [L42980, L45884, L45889] or with [rituximab].[L45884, L45889] - In Europe, it is approved for patients who have received at least one prior therapy or in first-line treatment for patients unsuitable for chemoimmunotherapy.[L45884] **Chronic graft-versus-host disease (cGVHD)** - In the US, it is approved in patients aged one year and older after the prior failure of one or more lines of systemic therapy.[L42980] - In Canada, it is approved in adults with steroid-dependent or refractory cGVHD.[L45889] **Mantle cell lymphoma (MCL)** - In Europe and Canada, ibrutinib is also indicated to treat relapsed or refractory MCL in adults.[L45884, L45889] **Marginal zone lymphoma (MZL)** - In Canada, it is approved for adults who require systemic therapy and have received at least one prior anti-CD20-based therapy.[L45889]
Categories
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
  • Bruton's tyrosine kinase (BTK) inhibitors
  • Cancer immunotherapy
  • Cytochrome P-450 CYP2D6 Substrates
ATC-CodeL01EL01
CAS number936563-96-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Tyrosine-protein kinase BTKMAAVILESIFLKRSQQKKKTSPLNFKKRLFLLTVHKLSYYEYDFERGRRG...unknowninhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 2D6MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...unknownsubstrate
Serum albuminMKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1873475
PubChem 24821094
ChEMBL CHEMBL1873475
ChEBI CHEBI:76612
CCDC/CSD HAWLUP, BETXEG, HAWLAV, RUYDEW01, HAWLEZ, BETWUV, LAGVEY, BETXEG01