Lapatinib

Lapatinib
Clinical data
Trade names	Tykerb, Tyverb, others
AHFS/Drugs.com	Monograph
MedlinePlus	a607055
License data	US DailyMed: Lapatinib;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth
ATC code	L01EH01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: WARNINGRx-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Variable, increased with food
Protein binding	>99%
Metabolism	Liver, mostly CYP3A-mediated (minor 2C19 and 2C8 involvement)
Elimination half-life	24 hours (repeated dosing), 14.2 hours (single dose)
Excretion	Mostly Feces
Identifiers
	IUPAC name N-[3-Chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-; [5-[(2-methylsulfonylethylamino)methyl]-2-furyl]; quinazolin-4-amine;
CAS Number	231277-92-2 ; as salt: 388082-78-8 ;
PubChem CID	208908;
IUPHAR/BPS	5692;
DrugBank	DB01259 ; as salt: DBSALT001785 ;
ChemSpider	181006 ; as salt: 9731817 ;
UNII	0VUA21238F; as salt: G873GX646R ;
KEGG	D08108 ; as salt: D04024 ;
ChEBI	CHEBI:49603 ;
ChEMBL	ChEMBL554 ; as salt: ChEMBL1201179 ;
PDB ligand	FMM (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID7046675 ;
Chemical and physical data
Formula	C29H26ClFN4O4S
Molar mass	581.06 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CS(=O)(=O)CCNCc1ccc(o1)c2ccc3c(c2)c(ncn3)Nc4ccc(c(c4)Cl)OCc5cccc(c5)F;
	InChI InChI=1S/C29H26ClFN4O4S/c1-40(36,37)12-11-32-16-23-7-10-27(39-23)20-5-8-26-24(14-20)29(34-18-33-26)35-22-6-9-28(25(30)15-22)38-17-19-3-2-4-21(31)13-19/h2-10,13-15,18,32H,11-12,16-17H2,1H3,(H,33,34,35) ; Key:BCFGMOOMADDAQU-UHFFFAOYSA-N ;
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Lapatinib (INN), used in the form of lapatinib ditosylate (USAN) (trade names Tykerb and Tyverb marketed by Novartis) is an orally active drug for breast cancer and other solid tumours.^[3] It is a dual tyrosine kinase inhibitor which interrupts the HER2/neu and epidermal growth factor receptor (EGFR) pathways.^[4] It is used in combination therapy for HER2-positive breast cancer. It is used for the treatment of patients with advanced or metastatic breast cancer whose tumors overexpress HER2 (ErbB2).^[5]

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
^ "Tyverb EPAR". European Medicines Agency (EMA). 10 June 2008. Retrieved 12 October 2024.
^ Burris HA (2004). "Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib". The Oncologist. 9 (Suppl 3): 10–15. doi:10.1634/theoncologist.9-suppl_3-10. PMID 15163842. S2CID 38907784.
^ Cite error: The named reference futuredrugs was invoked but never defined (see the help page).
^ "Breast cancer drug approved for new indication". Women's Health. 6 (2). Cancer.gov: 173. March 2010. doi:10.2217/whe.10.11. PMID 20187722.

[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.

[2] "Tyverb EPAR". European Medicines Agency (EMA). 10 June 2008. Retrieved 12 October 2024.

[pmid15163842-3] Burris HA (2004). "Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib". The Oncologist. 9 (Suppl 3): 10–15. doi:10.1634/theoncologist.9-suppl_3-10. PMID 15163842. S2CID 38907784.

[futuredrugs-4] Cite error: The named reference futuredrugs was invoked but never defined (see the help page).

[FDA-5] "Breast cancer drug approved for new indication". Women's Health. 6 (2). Cancer.gov: 173. March 2010. doi:10.2217/whe.10.11. PMID 20187722.

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