Afatinib

Afatinib
Clinical data
Trade names	Gilotrif, Giotrif, Afanix
Other names	BIBW 2992
AHFS/Drugs.com	Monograph
MedlinePlus	a613044
License data	EU EMA: by INN; US DailyMed: Afatinib;
Pregnancy; category	AU: C;
Routes of; administration	By mouth
ATC code	L01EB03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	95%
Metabolism	CYP not involved
Elimination half-life	37 hours
Excretion	Faeces (85%), urine (4%)
Identifiers
	IUPAC name N-[4-[(3-Chloro-4-fluorophenyl)amino]-7-[[(3S)-tetrahydro-3-furanyl]oxy]-6-quinazolinyl]-4(dimethylamino)-2-butenamide;
CAS Number	850140-72-6 [Drugbank];
PubChem CID	10184653;
IUPHAR/BPS	5667;
DrugBank	DB08916 ;
ChemSpider	8360155 ;
UNII	41UD74L59M;
KEGG	D09724 ; as salt: D09733 ;
ChEBI	CHEBI:61390 ;
ChEMBL	ChEMBL1173655 ;
CompTox Dashboard (EPA)	DTXSID20893451 ;
ECHA InfoCard	100.239.035
Chemical and physical data
Formula	C24H25ClFN5O3
Molar mass	485.94 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)C\C=C\C(=O)Nc3cc1c(Nc(cc2Cl)ccc2F)ncnc1cc3OC4COCC4;
	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 ; Key:ULXXDDBFHOBEHA-CWDCEQMOSA-N ;
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Afatinib, sold under the brand name Gilotrif among others, is a medication which is used to treat non-small cell lung carcinoma (NSCLC).^[2]^[3]^[4] It belongs to the tyrosine kinase inhibitor family of medications.^[5] It is taken by mouth.^[5]^[1]

It is mainly used to treating cases of NSCLC that harbour mutations in the epidermal growth factor receptor (EGFR) gene.^[6]

^ ^a ^b Cite error: The named reference Gilotrif FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Spreitzer was invoked but never defined (see the help page).
^ Cite error: The named reference Minkovsky was invoked but never defined (see the help page).
^ Cite error: The named reference FDA was invoked but never defined (see the help page).
^ ^a ^b Cite error: The named reference TGA was invoked but never defined (see the help page).
^ Vavalà T (2017). "Role of afatinib in the treatment of advanced lung squamous cell carcinoma". Clinical Pharmacology. 9: 147–157. doi:10.2147/CPAA.S112715. PMC 5709991. PMID 29225480.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.