Ibrutinib

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Ibrutinib are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Ibrutinib?

The molecule Ibrutinib presents a molecular formula of C25H24N6O2 and its IUPAC name is 1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one.

Ibrutinib (brand name Imbruvica) is a small molecule drug that inhibits Bruton's tyrosine kinase (BTK). BTK is a key signalling protein in B cells, which are a type of white blood cell involved in the immune response. Ibrutinib was approved by the US Food and Drug Administration (FDA) in November 2013 to treat mantle cell lymphoma (MCL), a type of blood cancer. It is also approved to treat chronic lymphocytic leukemia (CLL) and Waldenström macroglobulinaemia (WM)..

Ibrutinib is an inhibitor of BTK, a key signalling protein in B cells. BTK participes in the activation of B cells, which are a type of white blood cell involved in the immune response. Ibrutinib works by blocking the activity of BTK, which prevents the activation of B cells. This leads to a reduction in the number of B cells and a decrease in the activity of the immune system..

Ibrutinib was approved by the US Food and Drug Administration (FDA) in November 2013 to treat mantle cell lymphoma (MCL), a type of blood cancer. It is also approved to treat chronic lymphocytic leukemia (CLL) and Waldenström macroglobulinaemia (WM)..

Ibrutinib is generally well tolerated. The most common side effects are fatigue, diarrhoea, musculoskeletal pain, and bruising. Ibrutinib can also cause serious side effects, including bleeding, infection, and heart problems..

Ibrutinib is a small molecule drug that is taken orally. It exists as a capsule or tablet. The recommended dose is 420 mg once daily. Ibrutinib should be taken with food..

Ibrutinib is a targeted therapy that is used to treat blood cancers. It is a type of cancer that is characterized by the overproduction of B cells. Ibrutinib works by targeting and inhibiting the activity of Bruton's tyrosine kinase (BTK), which is a key signalling protein in B cells. Ibrutinib was approved by the US Food and Drug Administration (FDA) in November 2013 to treat mantle cell lymphoma (MCL), a type of blood cancer. It is also approved to treat chronic lymphocytic leukemia (CLL) and Waldenström macroglobulinaemia (WM)..

3D structure

Cartesian coordinates

Geometry of Ibrutinib in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Ibrutinib XYFPWWZEPKGCCK-GOSISDBHSA-N chemical compound 2D structure molecule svg
Ibrutinib

 

Molecule descriptors

 
IUPAC name1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
InChI codeInChI=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
InChI KeyXYFPWWZEPKGCCK-GOSISDBHSA-N
SMILESC=CC(=O)N1CCC[C@@H](n2nc(-c3ccc(Oc4ccccc4)cc3)c3c(N)ncnc32)C1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (R)-1-(3-(4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo-[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one
  • (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one
  • (R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one.
  • (R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-ylprop-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-((R)-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]-1-piperidinyl]-2-propen-1-one
  • 1-[(3R)-3-[4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-piperidinyl]-2-propen-1-one1-[(3R)-3-[4-AMino-3-(4-phenoxyphenyl)pyrazolo[3, 4-d]pyriMidin-1-yl]
  • 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
  • 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
  • 1X70OSD4VX
  • 2-Propen-1-one, 1-((3R)-3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo(3,4-d)pyrimidin-1-yl)-1-piperidinyl)-
  • 936563-96-1
  • A1-01649
  • AC-26942
  • AMY27873
  • BDBM50357312
  • BI164531
  • CRA 032765
  • CRA-032765
  • D10223
  • DB09053
  • EX-5960
  • EX-A066
  • GTPL6912
  • HSDB 8260
  • HY-10997
  • IMBRUVICA
  • Ibrutinib
  • Ibrutinib (JAN/USAN)
  • Ibrutinib (PCI-32765)
  • Ibrutinib- Bio-X
  • IbrutinibCI-32765mbruvica(R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one
  • Imbruvica; PCI-32765
  • J-523872
  • JNJ 02
  • MFCD20261150
  • MLS006010041
  • NCGC00187912-01
  • NCGC00187912-02
  • NCGC00187912-03
  • NCGC00187912-12
  • NSC-800769
  • NSC800769
  • PCI 32765
  • PCI-32765
  • PCI-32765 (Ibrutinib)
  • PCI-32765-00
  • PCI32765
  • Pc-32765
  • Q5984881
  • SMR004701213
  • SW218096-2
  • ibrutinibum
  • piperidin-1-yl]prop-2-en-1-one1-{3-[4-AMino-3-(4-phenoxy-phenyl)-pyrazolo[3,4-d]pyriMidin-1-yl]-piperidin-1-yl}-propenone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC35328014
  • UNII-1X70OSD4VX
  • AKOS022185476
  • DTXSID60893450
  • CHEMBL1873475
  • CHEBI:76612
  • SCHEMBL201859

Physico-Chemical properties

IUPAC name1-[(3R)-3-[4-amino-3-(4-phenoxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]piperidin-1-yl]prop-2-en-1-one
Molecular formulaC25H24N6O2
Molecular weight440.497
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity131.01
LogP4.7
Topological polar surface area99.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.