This HTML5 document contains 75 embedded RDF statements represented using HTML+Microdata notation.

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Namespace Prefixes

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Statements

Subject Item
n2:DB01259
rdf:type
n3:Drug
n3:description
Lapatinib is an anti-cancer drug developed by GlaxoSmithKline (GSK) as a treatment for solid tumours such as breast and lung cancer. It was approved by the FDA on March 13, 2007, for use in patients with advanced metastatic breast cancer in conjunction with the chemotherapy drug Capecitabine. Lapatinib is human epidermal growth factor receptor type 2 (HER2/ERBB2) and epidermal growth factor receptor (HER1/EGFR/ERBB1) tyrosine kinases inhibitor. It binds to the intracellular phosphorylation domain to prevent receptor autophosphorylation upon ligand binding.
n3:dosage
n18:271B600F-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Nelson MH, Dolder CR: Lapatinib: a novel dual tyrosine kinase inhibitor with activity in solid tumors. Ann Pharmacother. 2006 Feb;40(2):261-9. Epub 2006 Jan 17. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16418322 # Burris HA 3rd: Dual kinase inhibition in the treatment of breast cancer: initial experience with the EGFR/ErbB-2 inhibitor lapatinib. Oncologist. 2004;9 Suppl 3:10-5. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15163842 # Burris HA 3rd, Hurwitz HI, Dees EC, Dowlati A, Blackwell KL, O'Neil B, Marcom PK, Ellis MJ, Overmoyer B, Jones SF, Harris JL, Smith DA, Koch KM, Stead A, Mangum S, Spector NL: Phase I safety, pharmacokinetics, and clinical activity study of lapatinib (GW572016), a reversible dual inhibitor of epidermal growth factor receptor tyrosine kinases, in heavily pretreated patients with metastatic carcinomas. J Clin Oncol. 2005 Aug 10;23(23):5305-13. Epub 2005 Jun 13. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15955900 # Geyer CE, Forster J, Lindquist D, Chan S, Romieu CG, Pienkowski T, Jagiello-Gruszfeld A, Crown J, Chan A, Kaufman B, Skarlos D, Campone M, Davidson N, Berger M, Oliva C, Rubin SD, Stein S, Cameron D: Lapatinib plus capecitabine for HER2-positive advanced breast cancer. N Engl J Med. 2006 Dec 28;355(26):2733-43. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17192538 # Johnston SR, Leary A: Lapatinib: a novel EGFR/HER2 tyrosine kinase inhibitor for cancer. Drugs Today (Barc). 2006 Jul;42(7):441-53. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16894399 # Tevaarwerk AJ, Kolesar JM: Lapatinib: a small-molecule inhibitor of epidermal growth factor receptor and human epidermal growth factor receptor-2 tyrosine kinases used in the treatment of breast cancer. Clin Ther. 2009;31 Pt 2:2332-48. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20110044 # Medina PJ, Goodin S: Lapatinib: a dual inhibitor of human epidermal growth factor receptor tyrosine kinases. Clin Ther. 2008 Aug;30(8):1426-47. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18803986
n3:group
approved investigational
n3:halfLife
Single-dose terminal half life: 14.2 hours Effective multiple-dose half life: 24 hours
n3:indication
Indicated in combination with capecitabine for the treatment of patients with advanced or metastatic breast cancer whose tumors overexpress the human epidermal receptor type 2 (HER2) protein and who have received prior therapy including an anthracycline, a taxane, and trastuzuma.
owl:sameAs
n16:DB01259 n28:DB01259
dcterms:title
Lapatinib
adms:identifier
n14:5445 n17:49603 n19:46507141 n21:FMM n22:208908 n23:D04024 n24:0173-0752-00 n25:181006 n26:DB01259 n29:PA152241907 n30:Lapatinib
n3:mechanismOfAction
Lapatinib is a 4-anilinoquinazoline kinase inhibitor of the intracellular tyrosine kinase domains of both epidermal growth factor receptor (HER1/EGFR/ERBB1) and human epidermal growth factor receptor type 2 (HER2/ERBB2)with a dissociation half-life of ≥300 minutes. Lapatinib inhibits ERBB-driven tumor cell growth in vitro and in various animal models. An additive effect was demonstrated in an in vitro study when lapatinib and 5-florouracil (the active metabolite of capecitabine) were used in combination in the 4 tumor cell lines tested. The growth inhibitory effects of lapatinib were evaluated in trastuzumab-conditioned cell lines. Lapatinib retained significant activity against breast cancer cell lines selected for long-term growth in trastuzumab-containing medium in vitro. These in vitro findings suggest non-cross-resistance between these two agents.
n3:packager
n20:271B600D-363D-11E5-9242-09173F13E4C5
n3:patent
n6:7157466 n6:2317589 n6:2413134 n6:6391874
n3:routeOfElimination
Lapatinib undergoes extensive metabolism, primarily by CYP3A4 and CYP3A5, with minor contributions from CYP2C19 and CYP2C8 to a variety of oxidated metabolites, none of which accounts for more than 14% of the dose recovered in the feces or 10% of lapatinib concentration in plasma.
n3:synonym
GW 572016 N-(3-chloro-4-((3-Fluorophenyl)methoxy)phenyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)-2-furanyl)-4-quinazolinamine FMM Lapatinib ditosylate Lapatinib tosilate hydrate N-{3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}-6-[5-({[2-(methylsulfonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine Tykerb
n3:toxicity
There has been a report of one patient who took 3,000 mg of lapatinib for 10 days. This patient had grade 3 diarrhea and vomiting on day 10.
n3:proteinBinding
Highly bound (>99%) to albumin and alpha-1 acid glycoprotein
n3:synthesisReference
"DrugSyn.org":http://www.drugsyn.org/Lapatinib.htm
n11:hasConcept
n12:M0473129
foaf:page
n8:tykerb.htm n31:lapatinib.html
n3:IUPAC-Name
n4:271B6014-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B601A-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B6019-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B6016-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B6017-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B6018-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B6012-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B602A-363D-11E5-9242-09173F13E4C5 n4:271B6010-363D-11E5-9242-09173F13E4C5 n4:271B6013-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B6011-363D-11E5-9242-09173F13E4C5
n9:hasATCCode
n10:L01XE07
n3:H-Bond-Acceptor-Count
n4:271B6020-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B6021-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B601B-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B601C-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B601E-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B601D-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B601F-363D-11E5-9242-09173F13E4C5
n3:absorption
Absorption following oral administration of lapatinib is incomplete and variable.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
388082-78-8
n3:category
n3:containedIn
n5:271B600E-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B6026-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B6028-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B6029-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B6025-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B6024-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B6027-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B6015-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B6022-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B6023-363D-11E5-9242-09173F13E4C5