CHEBI:61390 - afatinib

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ChEBI Name afatinib
ChEBI ID CHEBI:61390
Definition A quinazoline compound having a 3-chloro-4-fluoroanilino group at the 4-position, a 4-dimethylamino-trans-but-2-enamido group at the 6-position, and an (S)-tetrahydrofuran-3-yloxy group at the 7-position. Used (as its dimaleate salt) for the first-line treatment of patients with metastatic non-small cell lung cancer.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C24H25ClFN5O3
Net Charge 0
Average Mass 485.93800
Monoisotopic Mass 485.163
InChI InChI=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
InChIKey ULXXDDBFHOBEHA-CWDCEQMOSA-N
SMILES CN(C)C\C=C\C(=O)Nc1cc2c(Nc3ccc(F)c(Cl)c3)ncnc2cc1O[C@H]1CCOC1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing afatinib (CHEBI:61390) has role antineoplastic agent (CHEBI:35610)
afatinib (CHEBI:61390) has role tyrosine kinase inhibitor (CHEBI:38637)
afatinib (CHEBI:61390) is a aromatic ether (CHEBI:35618)
afatinib (CHEBI:61390) is a enamide (CHEBI:51751)
afatinib (CHEBI:61390) is a furans (CHEBI:24129)
afatinib (CHEBI:61390) is a monochlorobenzenes (CHEBI:83403)
afatinib (CHEBI:61390) is a organofluorine compound (CHEBI:37143)
afatinib (CHEBI:61390) is a quinazolines (CHEBI:38530)
afatinib (CHEBI:61390) is a secondary carboxamide (CHEBI:140325)
afatinib (CHEBI:61390) is a tertiary amino compound (CHEBI:50996)
Incoming afatinib dimaleate (CHEBI:76003) has part afatinib (CHEBI:61390)
IUPAC Name
(2E)-N-{4-[(3-chloro-4-fluorophenyl)amino]-7-[(3S)-tetrahydrofuran-3-yloxy]quinazolin-6-yl}-4-(dimethylamino)but-2-enamide
INNs Sources
afatinib WHO MedNet
afatinib WHO MedNet
afatinib KEGG DRUG
afatinibum WHO MedNet
Synonym Source
BIBW 2992 ChEBI
Database Links Databases
0WM PDBeChem
4318 DrugCentral
Afatinib Wikipedia
D09724 KEGG DRUG
DB08916 DrugBank
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Registry Numbers Types Sources
11746023 Reaxys Registry Number Reaxys
850140-72-6 CAS Registry Number ChemIDplus
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Last Modified
07 March 2018