Afatinib (BIBW2992)

Names

[ Name ]:
Afatinib (BIBW2992)

[Synonym ]:
2-Butenamide, N-[4-[(3-chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4-(dimethylamino)-, (2E)-
(S,E)-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
(2E)-N-(4-[(3-chloro-4-fluorophenyl)amino]-7-{[(3S)-tetrahydrofuran-3-yl]oxy}quinazolin-6-yl)-4-(dimethylamino)but-2-enamide
Afatinib
Tovok
Tomtovok
BIBW2992
(2E)-N-{4-[(3-Chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydro-3-furanyloxy]-6-quinazolinyl}-4-(dimethylamino)-2-butenamide
Gilotrif
BIBW 2992

Biological Activity

[Description]:

(E/Z)-Afatinib ((E/Z)-BIBW 2992) is the mixture of (E)-Afatinib and (Z)-Afatinib. Afatinib (HY-10261) is an irreversible inhibitor of EGFR, by irreversibly binding to their ATP binding site to block activation of EGFR, HER2, HER4, and EGFRvIII. Afatinib used in co-administration with Temozolomide (HY-17364), potently targeting to EGFRvIII-cMet signaling in glioblastoma cells[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Signaling Pathways >> JAK/STAT Signaling >> EGFR

Research Areas >> Others

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Signaling Pathways >> PI3K/Akt/mTOR >> Akt

Signaling Pathways >> Protein Tyrosine Kinase/RTK >> c-Met/HGFR

[References]

[1]. Yoshioka T, et al. Antitumor activity of pan-HER inhibitors in HER2-positive gastric cancer. Cancer Sci. 2018 Apr;109(4):1166-1176.

[2]. Wang XK, et al. Afatinib circumvents multidrug resistance via dually inhibiting ATP binding cassette subfamily G member 2 in vitro and in vivo. Oncotarget. 2014 Dec 15;5(23):11971-85.

[3]. Li D, et al. BIBW2992, an irreversible EGFR/HER2 inhibitor highly effective in preclinical lung cancer models. Oncogene. 2008 Aug 7;27(34):4702-11.

[4]. Wong CH, et al. Preclinical evaluation of afatinib (BIBW2992) in esophageal squamous cell carcinoma (ESCC). Am J Cancer Res. 2015 Nov 15;5(12):3588-99.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
676.9±55.0 °C at 760 mmHg

[ Melting Point ]:
100 - 102 °C

[ Molecular Formula ]:
C₂₄H₂₅ClFN₅O₃

[ Molecular Weight ]:
485.94

[ Flash Point ]:
363.2±31.5 °C

[ Exact Mass ]:
485.162994

[ PSA ]:
88.61000

[ LogP ]:
3.59

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.668

[ Storage condition ]:
-20°C

Safety Information

[ Hazard Codes ]:
Xn

[ HS Code ]:
2934999090

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%