Bosutinib

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

What is the Bosutinib?

The molecule Bosutinib presents a molecular formula of C26H29Cl2N5O3 and its IUPAC name is 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile.

Bosutinib (INN, trade name Bosulif) is an antineoplastic agent used in the treatment of certain types of leukemia. It is a small molecule inhibitor of the Abl and Src tyrosine kinases..

Bosutinib was developed by Wyeth (now Pfizer) and is currently marketed by Pfizer. The U.S. Food and Drug Administration (FDA) granted accelerated approval for its use in the treatment of adults with Philadelphia chromosome-positive chronic myelogenous leukemia (CML) who are resistant or intolerant to prior therapy including imatinib..

In clinical trials, the most common adverse events (>20%) associated with bosutinib were diarrhea, nausea, vomiting, muscle pain, fatigue, and rash. The most common serious adverse events (>5%) were pleural effusion, pneumonia, and diarrhea..

Bosutinib is a kinase inhibitor that targets the Bcr-Abl kinase and Src family kinases. This results in the inhibition of cell proliferation and the induction of apoptosis..

Bosutinib has shown activity in patients with CML who are resistant or intolerant to prior therapy, including imatinib. In a phase II clinical trial, bosutinib was associated with a major cytogenetic response in 41% of patients with CML..

The recommended dose of bosutinib is 500 mg once daily. Bosutinib should be taken on an empty stomach, at least one hour before or two hours after a meal..

3D structure

Cartesian coordinates

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

2D drawing

 

Bosutinib UBPYILGKFZZVDX-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Bosutinib

 

Molecule descriptors

 
IUPAC name4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
InChI codeInChI=1S/C26H29Cl2N5O3/c1-32-6-8-33(9-7-32)5-4-10-36-25-13-21-18(11-24(25)35-3)26(17(15-29)16-30-21)31-22-14-23(34-2)20(28)12-19(22)27/h11-14,16H,4-10H2,1-3H3,(H,30,31)
InChI KeyUBPYILGKFZZVDX-UHFFFAOYSA-N
SMILESCOc1cc(Nc2c(C#N)cnc3cc(OCCCN4CCN(C)CC4)c(OC)cc23)c(Cl)cc1Cl

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.

  • 2-PYRIDIN-2-YLETHYLACETATE
  • 3-QUINOLINECARBONITRILE, 4-((2,4-DICHLORO-5-METHOXYPHENYL)AMINO)-6-METHYL-1-PIPERAZINYL)PROPOXY)-
  • 3-Quinolinecarbonitrile, 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-
  • 380843-75-4
  • 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)-3-quinolinecarbonitrile
  • 4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile
  • 4-(2,4-Dichloro-5-methoxy-phenylamino)-6-methoxy-7-[3-(4-methyl-piperazin-1-yl)propoxy]quinoline-3-carbonitrile
  • 4-(2,4-dichloro-5-methoxy-anilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
  • 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
  • 4-(2,4-dichloro-5-methoxyphenylamino)-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinoline-3-carbonitrile
  • 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile
  • 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
  • 5018V4AEZ0
  • 843B754
  • A25014
  • AB01565836_03
  • AC-2413
  • AMY266
  • AS-11064
  • BCP01782
  • BCP9000446
  • BCPP000318
  • BDBM4552
  • BOSULIF
  • BOSUTINIB ISOMER 1
  • Bosutinib
  • Bosutinib (SKI-606)
  • Bosutinib (SKI606)
  • Bosutinib (USAN)
  • Bosutinib (as monohydrate)
  • Bosutinib - SKI-606
  • Bosutinib,SKI-606
  • CCG-208129
  • CS-0118
  • D03252
  • DB06616
  • EC 700-455-1
  • EX-A391
  • FT-0656231
  • GTPL5710
  • HMS2043A22
  • HMS3244A03
  • HMS3244A04
  • HMS3244B03
  • HMS3651C03
  • HMS3672K11
  • HMS3743E09
  • HY-10158
  • J-519931
  • K00615a
  • MFCD07367846
  • MLS006011212
  • NCGC00241107-01
  • NCGC00241107-03
  • NCGC00241107-05
  • NSC-765694
  • NSC-799367
  • NSC765694
  • NSC799367
  • PB30881
  • PF-5208763
  • Q-200745
  • Q894611
  • S1014
  • SK 606
  • SK-606
  • SKI 606
  • SKI-606
  • SKI-606)
  • SKI-606;4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[3-(4-methyl-1-piperazinyl)propoxy]-3-quinolinecarbonitrile
  • SKI606
  • SKI606; SKI 606; SK-I606
  • SMR002530350
  • SR-01000941572
  • SR-01000941572-1
  • SW220197-1

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC22448983
  • UNII-5018V4AEZ0
  • AKOS015902521
  • BRD-K99964838-001-01-0
  • BRD-K99964838-001-06-9
  • DTXSID10861568
  • CHEMBL288441
  • CHEBI:39112
  • SCHEMBL158390

Physico-Chemical properties

IUPAC name4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline-3-carbonitrile
Molecular formulaC26H29Cl2N5O3
Molecular weight530.446
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity150.66
LogP5.1
Topological polar surface area82.9

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.