Afatinib (BIBW2992)

Afatinib (BIBW2992) irreversibly inhibits EGFR/HER2 including EGFR(wt), EGFR(L858R), EGFR(L858R/T790M) and HER2 with IC50 of 0.5 nM, 0.4 nM, 10 nM and 14 nM in cell-free assays, respectively; 100-fold more active against Gefitinib-resistant L858R-T790M EGFR mutant.

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Afatinib (BIBW2992) Chemical Structure

Afatinib (BIBW2992) Chemical Structure
Molecular Weight: 485.94

Validation & Quality Control

Product Use Citation(34)

Customer Product Validation(3)

Quality Control & MSDS

Related Compound Libraries

EGFR Inhibitors with Unique Features

  • Selective EGFR Inhibitor

    Erlotinib HCl (OSI-744) EGFR-selective, IC50=2 nM.

  • FDA-approved EGFR Inhibitor

    Lapatinib Approved by FDA for breast cancer.

  • Newest EGFR Inhibitor

    CO-1686 (AVL-301) Irreversible, mutant-selective EGFR inhibitor with Ki of 21.5 nM and 303.3 nM for EGFRL858R/T790M and EGFRWT, respectively.

  • Classic EGFR Inhibitor

    WZ4002 Mutant-selective EGFR inhibitor for EGFR(L858R)/(T790M) with IC50 of 2 nM/8 nM.

Product Information

  • Compare EGFR Inhibitors
    Compare EGFR Products
  • Research Area
  • Inhibition Profile
  • Afatinib (BIBW2992) Mechanism
  • Combination Therapy
    Combination Therapy

Product Description

Biological Activity

Description Afatinib (BIBW2992) irreversibly inhibits EGFR/HER2 including EGFR(wt), EGFR(L858R), EGFR(L858R/T790M) and HER2 with IC50 of 0.5 nM, 0.4 nM, 10 nM and 14 nM in cell-free assays, respectively; 100-fold more active against Gefitinib-resistant L858R-T790M EGFR mutant.
Targets EGFR (L858R) [1]
(Cell-free assay)
EGFR (wt) [1]
(Cell-free assay)
EGFR (L858R/T790M) [1]
(Cell-free assay)
HER2 [1]
(Cell-free assay)
IC50 0.4 nM 0.5 nM 10 nM 14 nM
In vitro BIBW2992 shows potent activity against both wild-type and mutant forms of EGFR and HER2. It is similar to Gefitinib in potency against L858R EGFR, but about 100-fold more active against the Gefitinib resistant L858R-T790M EGFR double mutant. BIBW2992 exhibits potent effects on both EGFR and HER2 phosphorylation in vivo. It compares favorably to reference compounds (such as Lapatinib et al.) in all cell types tested, such as human epidermoid carcinoma cell line A431 expressing wt EGFR, murine NIH-3T3 cells transfected with wt HER2, as well as breast cancer cell line BT-474 and gastric cancer cell line NCI-N87, which express endogenous HER2. [1]
Cell Data
Cell LinesAssay TypeConcentrationIncubation TimeFormulationActivity DescriptionPMID
HDLM-2MV3Hdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?MmHzTWM2OD1yLkCwOVczKM7:TR?=Mof5V2FPT0WU
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HCC2218M2HBZmdzd3e2aDDJcohq[mm2aX;uJGF{e2G7Mnv6TWM2OD1yLkCwPVg4KM7:TR?=MmHEV2FPT0WU
KARPAS-45M4jHT2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7NVntcpFXUUN3ME2wMlAyPjdzIN88US=>NYPVWnVrW0GQR1XS
HSC-4M1jxfmdzd3e2aDDJcohq[mm2aX;uJGF{e2G7MUjJR|UxRTBwMEG3OFgh|ryPNVvh[ZJoW0GQR1XS
CHL-1MYPHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?NYjSRW8zUUN3ME2wMlAyQDN7IN88US=>NIP0O2dUSU6JRWK=
KY821MlS4S5Jwf3SqIFnubIljcXSrb36gRZN{[Xl?NX3qcphvUUN3ME2wMlAzODZizszNM3u0XXNCVkeHUh?=
NCI-N87M2T4fGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7MVLJR|UxRTBwMEK3O|Mh|ryPNYTn[G1QW0GQR1XS
DOKNVTYcId[T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm=MnLYTWM2OD1yLkCzNVk1KM7:TR?=NYL5NVNPW0GQR1XS
DSH1MlexS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl?MoPUTWM2OD1yLkCzN|E1KM7:TR?=NFfLUXRUSU6JRWK=
MDA-MB-175-VIINHr4OW5Iem:5dHigTY5pcWKrdHnvckBCe3OjeR?=NFW0SJZKSzVyPUCuNFM1OTZizszNNYnMeXRKW0GQR1XS
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EFO-27NIfnSWdIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=NYPNbXNXUUN3ME2wMlA2OTh{IN88US=>MmnvV2FPT0WU
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NCI-H292NGPhSopIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=NH\Ec4FKSzVyPUCuNFYxQSEQvF2=MV7TRW5ITVJ?
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NCI-H526NFLId3VIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=MoDzTWM2OD1yLkC3PFI{KM7:TR?=MYrTRW5ITVJ?
NCI-H1623NUfEeZU2T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm=MmLDTWM2OD1yLkC4NFI2KM7:TR?=MnTFV2FPT0WU
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UACC-893M1i1WGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7NXrzeZRvUUN3ME2wMlEyQDh3IN88US=>NH73cXFUSU6JRWK=
LU-65NGnsPItIem:5dHigTY5pcWKrdHnvckBCe3OjeR?=M4rXemlEPTB;MD6xNlY{OyEQvF2=Mn3oV2FPT0WU
HNMUDHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?MWrJR|UxRTBwMUOwO|ch|ryPM4H6eXNCVkeHUh?=
TI-73NU\KbG52T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm=MkOzTWM2OD1yLkG0O|E2KM7:TR?=MlL3V2FPT0WU
KU812NUDOTVlIT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm=Mlz4TWM2OD1yLkG1OFU3KM7:TR?=M4L3U3NCVkeHUh?=
SW13M4nUcmdzd3e2aDDJcohq[mm2aX;uJGF{e2G7MkDITWM2OD1yLkG2NlE3KM7:TR?=MmnZV2FPT0WU
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BV-173NWTJOZl3T3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm=NGK0bHZKSzVyPUCuNVc2QTZizszNMonEV2FPT0WU
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CAL-33M4TXNGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7NXjH[Y92UUN3ME2wMlIxOTh2IN88US=>NWPwZ2p2W0GQR1XS
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COR-L105MX7Hdo94fGhiSX7obYJqfGmxbjDBd5NigQ>?NYTuRWdoUUN3ME2wMlIyODh2IN88US=>MXvTRW5ITVJ?
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... Click to View More Cell Line Experimental Data

In vivo Daily oral administration of BIBW2992 at 20 mg/kg for 25 days results in dramatic tumor regression with a cumulative treated/control tumor volume ratio (T/C ratio) of 2%. Reduced phosphorylation of EGFR and AKT is confirmed by immunohistochemical staining of tissue sections. Therefore, like lapatinib and neratinib, BIBW2992 is a next generation tyrosine kinase inhibitor (TKI) that inhibits human epidermal growth factor receptor 2 (Her2) and epidermal growth factor receptor (EGFR) kinases irreversibly. BIBW2992 is not only active against EGFR mutations targeted by first generation TKIs like Erlotinib or Gefitinib, but also against those insensitive to these standard therapies. [1]
Features

Protocol(Only for Reference)

Kinase Assay:

[1]

In vitro kinase activity assays The wild type tyrosine kinase domain of the human EGFR as well as that of the EGFR L858R/T790M double mutant are fused to Glutathione-S-transferase (GST), and extracted. Enzyme activity is then assayed in the presence of the inhibitor BIBW2992, serially diluted in 50% DMSO. A random polymer pEY (4:1) is used as substrate and biotinylated pEY (bio-pEY) is added as a tracer substrate. The kinase domain of HER2 is cloned using the baculovirus system and extracted similarly to that of EGFR kinase. Details of assays for EGFR, HER2, SRC, BIRK and VEGFR2 kinase activity are available in Supplementary information.

Cell Assay:

[1]

Cell lines NSCLC cells
Concentrations 0-10 μM
Incubation Time 1 hour
Method

1 × 104 NSCLC cells are transferred into each well of a 96-well plate and cultured overnight in serum-free media for the EGFR phosphorylation assay. After addition of BIBW2992 on the next day, the plates are incubated at 37 °C for 1 hour. EGF-stimulation is done using 100 ng/mL for 10 min at room temperature. Cells are washed with ice cold PBS, extracted with 120 μL HEPEX buffer per well and shaken at room temperature for 1 hour. In all 2 × 104 cells per well is used for the HER2 phosphorylation assay. Streptavidin precoated plates are coated with anti-EGFR-biotin at 1:100 dilution in blocking buffer and c-erb2/HER2 oncoprotein Ab-5(Clone N24)-Biotin. Cell extracts is then transferred to the antibody-coated wells and incubated at room temperature for 1 hour. Extinction is measured at 450 nm.

Animal Study:

[1]

Animal Models Athymic NMRI-nu/nu female mice
Formulation In 0.5% methocellulose-0.4% polysorbate-80 (Tween 80)
Dosages 20 mg/kg
Administration Oral administration

Conversion of different model animals based on BSA (Value based on data from FDA Draft Guidelines)

SpeciesMouseRatRabbitGuinea pigHamsterDog
Weight (kg)0.020.151.80.40.0810
Body Surface Area (m2)0.0070.0250.150.050.020.5
Km factor36128520
Animal A (mg/kg) = Animal B (mg/kg) multiplied by  Animal B Km
Animal A Km

For example, to modify the dose of resveratrol used for a mouse (22.4 mg/kg) to a dose based on the BSA for a rat, multiply 22.4 mg/kg by the Km factor for a mouse and then divide by the Km factor for a rat. This calculation results in a rat equivalent dose for resveratrol of 11.2 mg/kg.

Rat dose (mg/kg) = mouse dose (22.4 mg/kg) ×  mouse Km(3)  = 11.2 mg/kg
rat Km(6)
1

References

[1] Li D, et al. Oncogene, 2008, 27(34), 4702-4711.

Clinical Trial Information( data from http://clinicaltrials.gov, updated on 2016-01-10)

NCT Number Recruitment Conditions Sponsor
/Collaborators
Start Date Phases
NCT02629523 Not yet recruiting Lung Neoplasms|EGFR Gene Mutation Chonnam National University Hospital March 2016 Phase 2
NCT02470065 Not yet recruiting Non Small Cell Lung Cancer European Organisation for Research and Treatment of Cance  ...more European Organisation for Research and Treatment of Cancer - EORTC January 2016 Phase 2
NCT02183883 Not yet recruiting Non-small Cell Lung Cancer University College, London|Boehringer Ingelheim December 2015 Phase 2
NCT02597946 Not yet recruiting Carcinoma, Non-Small-Cell Lung Boehringer Ingelheim December 2015 Phase 2
NCT02488694 Recruiting Non-small-cell Lung Cancer With Somatic EGFR Mutations AIO-Studien-gGmbH|Boehringer Ingelheim November 2015 Phase 2

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Chemical Information

Download Afatinib (BIBW2992) SDF
Molecular Weight (MW) 485.94
Formula

C24H25ClFN5O3

CAS No. 439081-18-2
Storage 3 years -20℃powder
6 months-80℃in solvent
Synonyms N/A
Solubility (25°C) * In vitro DMSO 97 mg/mL (199.61 mM)
Ethanol 15 mg/mL (30.86 mM)
Water <1 mg/mL (<1 mM)
In vivo 0.5% methylcellulose/0.2% Tween 80 30 mg/mL
* <1 mg/ml means slightly soluble or insoluble.
* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.
Chemical Name (S,E)-N-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-4-(dimethylamino)but-2-enamide

Customer Product Validation (3)


Click to enlarge
Rating
Source Int J Proteomics 2011 2011, 215496. Afatinib (BIBW2992) purchased from Selleck
Method CEER assay
Cell Lines H460/A549/RFU cell lines
Concentrations 0-10 μM
Incubation Time 4 h
Results This data showed that a potent dose-dependent inhibition of the HER1 and HER2 pathways in the HCC827 cells was observed by treatment with BIBW-2992. Other HER1 and/or HER2 pathway-activated cell lines, H1975 and H1650, were likewise had these pathway activations blocked by the treatment with BIBW-2992.

Click to enlarge
Rating
Source Int J Proteomics 2011 2011, 215496. Afatinib (BIBW2992) purchased from Selleck
Method Nikon inverted-phase microscope
Cell Lines lung tumor cell lines
Concentrations 0.1/1 µM
Incubation Time two weeks
Results Reduction of cell colony size formation was observed by the treatment with the irreversible HER1/2 inhibitor BIBW-2992 in H1975 and H1650 cells as seen when these cells were grown in an anchorage-dependent manner.

Click to enlarge
Rating
Source Dr. Zhang of Tianjin Medical University. Afatinib (BIBW2992) purchased from Selleck
Method Western blot
Cell Lines Breast cancer cells
Concentrations 0-1 nM
Incubation Time 3 h
Results BIBW2992 treatment resulted in a reduction of EGFR phosphorylation in Breast cancer cells.

Product Use Citation (34)

Tech Support & FAQs

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

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