afatinib

Also known as BIBW2992, Gilotrif®, BIBW 2992, Afatinibum

Afatinib, sold under the brand name Gilotrif among others, is a medication which is used to treat non-small cell lung carcinoma (NSCLC). It belongs to the tyrosine kinase inhibitor family of medications. It is taken by mouth.

Key facts

Drug.licence_EU: yes
Drug.protein_bound: 95%
Drug.Verifiedfields: changed
Drug.verifiedrevid: 645735594
Drug.image: Afatinib2DACS.svg
Drug.image_class: skin-invert-image
Drug.image2: Afatinib 3D ball-and-stick 4G5P.png
Drug.image_class2: bg-transparent
Drug.tradename: Gilotrif, Giotrif, Afanix
Drug.MedlinePlus: a613044
Drug.DailyMedID: Afatinib
Drug.pregnancy_AU: C
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: L01
Drug.ATC_suffix: EB03
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM

via Wikipedia infobox

Chemical data

Formula: C24H25ClFN5O3
Molecular weight: 485.9 g/mol
IUPAC name: (E)-N-[4-(3-chloro-4-fluoroanilino)-7-[(3S)-oxolan-3-yl]oxyquinazolin-6-yl]-4-(dimethylamino)but-2-enamide
SMILES: CN(C)C/C=C/C(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)O[C@H]4CCOC4
InChIKey: ULXXDDBFHOBEHA-CWDCEQMOSA-N
XLogP: 3.6
Polar surface area: 88.6 Å²
H-bond donors: 2
H-bond acceptors: 8
Formal charge: 0

via PubChem

Research

2,631 papers

Afatinib.Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer · 2018
Pragmatic Randomized Study of Afatinib Versus Chemotherapy for Patients With Non-Small Cell Lung Cancer With Uncommon Epidermal Growth Factor Receptor Mutations: ACHILLES/TORG1834.Journal of clinical oncology : official journal of the American Society of Clinical Oncology · 2025
Afatinib for the Treatment of NSCLC with Uncommon EGFR Mutations: A Narrative Review.Current oncology (Toronto, Ont.) · 2023
Afatinib-induced toxic epidermal necrolysis: A case report with a literature review.British journal of clinical pharmacology · 2024
Afatinib and Erlotinib in the treatment of squamous-cell lung cancer.Expert opinion on pharmacotherapy · 2018

via PubMed

Wikidata facts

Mass: 485.163

Show 5 more facts

chemical formula: C₂₄H₂₅ClFN₅O₃
isomeric SMILES: CN(C)C/C=C/C(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)O[C@H]4CCOC4
canonical SMILES: CN(C)CC=CC(=O)NC1=C(C=C2C(=C1)C(=NC=N2)NC3=CC(=C(C=C3)F)Cl)OC4CCOC4
World Health Organisation international non-proprietary name: afatinib
Commons category: Afatinib

Sources (5)

via Wikidata · CC0

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