Afatinib

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

What is the Afatinib?

The molecule Afatinib presents a molecular formula of C24H25ClFN5O3 and its IUPAC name is (E)-N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide.

Afatinib is a medication used to treat non-small cell lung cancer (NSCLC). It belongs to a class of drugs known as kinase inhibitors, which work by blocking the action of certain proteins called tyrosine kinases that are involved in the growth and survival of cancer cells. Afatinib specifically targets a protein called epidermal growth factor receptor (EGFR), which is often overactive in NSCLC..

Afatinib is typically taken orally, in the form of a tablet. It is usually taken once a day, with or without food. The dose of afatinib may need to be adjusted based on the individual's response to treatment and any side effects that may occur. It is important to follow the instructions of a healthcare provider when taking this medication..

Afatinib may cause side effects in some people, such as diarrhea, rash, and nausea. It may also cause serious side effects, such as liver damage, lung inflammation, and heart problems. It is important to report any side effects to a healthcare provider..

Afatinib should be used with caution in people with certain conditions, such as liver or kidney disease, or a history of heart problems. It may also interact with other medications, so it is important to inform a healthcare provider about all medications being taken..

Summary

From all the above, this molecule is a medication used to treat non-small cell lung cancer by blocking the action of certain proteins that are involved in the growth and survival of cancer cells. It is taken orally, usually once a day, and may cause side effects, including serious side effects. It is important to follow the instructions of a healthcare provider and to inform them about all medications being taken when using afatinib..

3D structure

Cartesian coordinates

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

2D drawing

 

Afatinib ULXXDDBFHOBEHA-CWDCEQMOSA-N chemical compound 2D structure molecule svg
Afatinib

 

Molecule descriptors

 
IUPAC name(E)-N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide
InChI codeInChI=1S/C24H25ClFN5O3/c1-31(2)8-3-4-23(32)30-21-11-17-20(12-22(21)34-16-7-9-33-13-16)27-14-28-24(17)29-15-5-6-19(26)18(25)10-15/h3-6,10-12,14,16H,7-9,13H2,1-2H3,(H,30,32)(H,27,28,29)/b4-3+/t16-/m0/s1
InChI KeyULXXDDBFHOBEHA-CWDCEQMOSA-N
SMILESCN(C)C/C=C/C(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[C@H]1CCOC1

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.

  • (2E)-N-(4-(3-chloro-4-fluoroanilino)-7-(((3S)-oxolan-3-yl)oxy)quinoxazolin-6-yl)-4-(dimethylamino)but-2-enamide
  • (2E)-N-[4-(3-Chloro-4-fluoroanilino)-7-[[(3S)-oxolane-3-yl]oxy]quinazoline-6-yl]-4-(dimethylamino)-2-buteneamide
  • (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-oxolan-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
  • (2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
  • (2e)-n-(4-((3-chloro-4-fluorophenyl)amino)-7-(((3s)-tetrahydro-3-furanyl)oxy)-6-quinazolinyl)-4-(dimethylamino)-2-butenamide
  • (E)-4-Dimethylamino-but-2-enoic acid-[4-(3-chloro-4-fluoro-phenylamino)-7-((S)-tetrahydrofuran-3-yloxy)-quinazolin-6-yl]-amide
  • (E)-4-dimethylamino-but-2-enoic acid-(4-(3-chloro-4-fluoro-phenylamino)-7-((S)-tetrahydrofuran-3-yloxy)-quinazolin-6-yl)-amide
  • (E)-4-dimethylamino-but-2-enoic acid-(4-(3-chloro-4-fluoro-phenylamino)-7-((S)-tetrahydrofuran-3-yloxy)-quinazolin-6yl)-amide
  • (E)-N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide
  • (E/Z)-Afatinib
  • (R,E)-N-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
  • (S)-N-(4-((3-Chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
  • (S)-N-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
  • (S,E)-N-(4-((3-Chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
  • (S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide.
  • (S,E)-N-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
  • 081B182
  • 2-Butenamide, N-(4-((3-chloro-4-fluorophenyl)amino)-7-(((3S)-tetrahydro-3-furanyl)oxy)-6-quinazolinyl)-4-(dimethylamino)-, (2E)-
  • 2-Butenamide, N-[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-, (2E)-
  • 2-butenamide, N-(4-((3-chloro-4-fluorophenyl)amino)-7-(((3S)-tetrahydro-3-furanyl)oxy)- 6-quinazolinyl)-4-(dimethylamino)-, (2E)-
  • 41UD74L59M
  • 439081-18-2
  • 850140-72-6
  • 850140-72-6 (free base)
  • A15572
  • AB01565886_02
  • AC-26079
  • AC-27018
  • AM808098
  • AS-80916
  • Afatinib
  • Afatinib (BIBW2992)
  • Afatinib (USAN/INN)
  • Afatinib free base
  • Afatinib(cis-trans isomerismtautomers)
  • Afatinib, Free Base
  • Afatinib- Bio-X
  • BA164141
  • BCP01779
  • BCP9000407
  • BCPP000338
  • BDBM50322823
  • BIBW 2992
  • BIBW-2992
  • BIBW2992
  • BIBW2992 (Tovok)
  • BIBW2992 - Afatinib
  • BIBW2992,Afatinib
  • C24H25ClFN5O3
  • CCG-264776
  • CS-0020030
  • D09724
  • DB08916
  • DS-14172
  • EX-8656
  • EX-A065
  • GTPL5667
  • J-500781
  • J-502300
  • MFCD12407405
  • MLS006010000
  • N-[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-2-Butenamide
  • NCGC00185000-01
  • NSC-750691
  • NSC-799327
  • NSC750691
  • NSC799327
  • Q4688818
  • S1011
  • SMR004701084
  • SR-01000941576
  • SR-01000941576-1
  • SW219248-1
  • Tomtovok
  • Tovok
  • afatinibum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3976838
  • UNII-41UD74L59M
  • AKOS015850681
  • AKOS015904219
  • AKOS025149636
  • BRD-K66175015-001-01-7
  • DTXSID20893451
  • CHEMBL1173655
  • CHEBI:61390
  • CHEBI:94698

Physico-Chemical properties

IUPAC name(E)-N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide
Molecular formulaC24H25ClFN5O3
Molecular weight485.938
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity129.90
LogP4.5
Topological polar surface area88.6

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.