lapatinib

Also known as LAP016, FMM, GW 572016, GW572016, N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine, N-{3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furanyl]-4-quinazolinamine

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. It is a dual tyrosine kinase inhibitor which interrupts the HER2/neu and epidermal growth factor receptor (EGFR) pathways. 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).

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 462089041
Drug.image: Lapatinib.svg
Drug.image_class: skin-invert-image
Drug.width: 275
Drug.tradename: Tykerb, Tyverb, others
Drug.MedlinePlus: a607055
Drug.DailyMedID: Lapatinib
Drug.pregnancy_AU: C
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: L01
Drug.ATC_suffix: EH01
Drug.legal_AU: S4
Drug.legal_CA: Rx-only
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.legal_EU: Rx-only

via Wikipedia infobox

Chemical data

Formula: C29H26ClFN4O4S
Molecular weight: 581.1 g/mol
IUPAC name: N-[3-chloro-4-[(3-fluorophenyl)methoxy]phenyl]-6-[5-[(2-methylsulfonylethylamino)methyl]furan-2-yl]quinazolin-4-amine
SMILES: CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl
InChIKey: BCFGMOOMADDAQU-UHFFFAOYSA-N
XLogP: 5.1
Polar surface area: 115 Å²
H-bond donors: 2
H-bond acceptors: 9
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2007
Admin. routes: oral
Indications: neoplasm, head and neck squamous cell carcinoma, breast carcinoma, breast neoplasm

via ChEMBL · EBI

Research

3,736 papers

Lapatinib as first-line treatment for muscle-invasive urothelial carcinoma in dogs.Scientific reports · 2022
Lapatinib.Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer · 2018
PI3K PROTAC overcomes the lapatinib resistance in PIK3CA-mutant HER2 positive breast cancer.Cancer letters · 2024
Lapatinib in breast cancer.Annals of oncology : official journal of the European Society for Medical Oncology · 2007
Lapatinib side-effect management.Clinical journal of oncology nursing · 2010

via PubMed

Wikidata facts

Subclass of: heterocyclic compound
Has part: carbon
Mass: 580.135
Has use: medication

Show 8 more facts

chemical formula: C₂₉H₂₆ClFN₄O₄S
significant drug interaction: posaconazole
Commons category: Lapatinib
World Health Organisation international non-proprietary name: lapatinib
canonical SMILES: CS(=O)(=O)CCNCC1=CC=C(O1)C2=CC3=C(C=C2)N=CN=C3NC4=CC(=C(C=C4)OCC5=CC(=CC=C5)F)Cl
subject has role: antineoplastic
physically interacts with: Erb-b2 receptor tyrosine kinase 2
legal status (medicine): boxed warning

Sources (6)

via Wikidata · CC0

~6 min read

Encyclopedic overview

9 sections

Contents

Status
Mode of action
Biochemistry
Clinical application
Breast cancer
Adverse effects
Ongoing trials in gastric cancer
References
External links

==Status== In March 2007, the U.S. Food and Drug Administration (FDA) approved lapatinib in combination therapy for breast cancer patients already using capecitabine (Xeloda). In January 2010, Tykerb received accelerated approval for the treatment of postmenopausal women with hormone receptor positive metastatic breast cancer that overexpresses the HER2 receptor and for whom hormonal therapy is indicated (in combination with letrozole).

Excerpted from Wikipedia’s “lapatinib” article, available under the CC BY-SA 4.0 licence.

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