This HTML5 document contains 81 embedded RDF statements represented using HTML+Microdata notation.

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Namespace Prefixes

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Statements

Subject Item
n2:DB01030
rdf:type
n5:Drug
n5:description
An antineoplastic agent used to treat ovarian cancer. It works by inhibiting DNA topoisomerases, type I. [PubChem]
n5:dosage
n22:271B564D-363D-11E5-9242-09173F13E4C5 n22:271B564E-363D-11E5-9242-09173F13E4C5 n22:271B564F-363D-11E5-9242-09173F13E4C5 n22:271B5649-363D-11E5-9242-09173F13E4C5 n22:271B564A-363D-11E5-9242-09173F13E4C5 n22:271B564B-363D-11E5-9242-09173F13E4C5 n22:271B564C-363D-11E5-9242-09173F13E4C5
n5:generalReferences
# Kollmannsberger C, Mross K, Jakob A, Kanz L, Bokemeyer C: Topotecan - A novel topoisomerase I inhibitor: pharmacology and clinical experience. Oncology. 1999;56(1):1-12. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9885371 # Herben VM, ten Bokkel Huinink WW, Beijnen JH: Clinical pharmacokinetics of topotecan. Clin Pharmacokinet. 1996 Aug;31(2):85-102. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8853931 # Dennis MJ, Beijnen JH, Grochow LB, van Warmerdam LJ: An overview of the clinical pharmacology of topotecan. Semin Oncol. 1997 Feb;24(1 Suppl 5):S5-12-S5-18. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/9122737
n5:group
investigational approved
n5:halfLife
2-3 hours
n5:indication
For the treatment of advanced ovarian cancer in patients with disease that has recurred or progressed following therapy with platinum-based regimens. Also used as a second-line therapy for treatment-sensitive small cell lung cancer, as well as in combination with cisplatin for the treatment of stage IV-B, recurrent, or persistent cervical cancer not amenable to curative treatment with surgery and/or radiation therapy.
owl:sameAs
n21:DB01030 n30:DB01030
dcterms:title
Topotecan
adms:identifier
n9:DB01030 n12:54705 n13:TTC n14:PA451729 n15:C11158 n16:0007-4201-01 n25:Topotecan n28:60700 n29:46505204
n5:mechanismOfAction
Topotecan has the same mechanism of action as irinotecan and is believed to exert its cytotoxic effects during the S-phase of DNA synthesis. Topoisomerase I relieves torsional strain in DNA by inducing reversible single strand breaks. Topotecan binds to the topoisomerase I-DNA complex and prevents religation of these single strand breaks. This ternary complex interferes with the moving replication fork, which leads to the induction of replication arrest and lethal double-stranded breaks in DNA. As mammalian cells cannot efficiently repair these double strand breaks, the formation of this ternary complex eventually leads to apoptosis (programmed cell death). Topotecan mimics a DNA base pair and binds at the site of DNA cleavage by intercalating between the upstream (−1) and downstream (+1) base pairs. Intercalation displaces the downstream DNA, thus preventing religation of the cleaved strand. By specifically binding to the enzyme–substrate complex, Topotecan acts as an uncompetitive inhibitor.
n5:packager
n23:271B5645-363D-11E5-9242-09173F13E4C5 n23:271B5644-363D-11E5-9242-09173F13E4C5
n5:patent
n17:5004758 n17:5674872 n17:2103707 n17:2103708
n5:routeOfElimination
Renal clearance is an important determinant of topotecan elimination. In a mass balance/excretion study in 4 patients with solid tumors, the overall recovery of total topotecan and its N-desmethyl metabolite in urine and feces over 9 days averaged 73.4 ± 2.3% of the administered IV dose. Fecal elimination of total topotecan accounted for 9 ± 3.6% while fecal elimination of N-desmethyl topotecan was 1.7 ± 0.6%.
n5:synonym
Topotecane Topotecanum 9-[(dimethylamino)Methyl]-10-hydroxy-(4S)-camptothecin
n5:toxicity
The primary anticipated complication of overdosage would consist of bone marrow suppression.
n18:hasAHFSCode
n27:10-00-00
n5:proteinBinding
35%
n5:salt
n5:synthesisReference
Venkata Raghavendra Palle, Sekhar Nariyam, Lankeshwara Matti, "PROCESS FOR PREPARING TOPOTECAN." U.S. Patent US20070149783, issued June 28, 2007.
n10:hasConcept
n11:M0029340
foaf:page
n4:topotec.htm n24:topotecan.html
n5:IUPAC-Name
n7:271B5654-363D-11E5-9242-09173F13E4C5
n5:InChI
n7:271B565A-363D-11E5-9242-09173F13E4C5
n5:Molecular-Formula
n7:271B5659-363D-11E5-9242-09173F13E4C5
n5:Molecular-Weight
n7:271B5656-363D-11E5-9242-09173F13E4C5
n5:Monoisotopic-Weight
n7:271B5657-363D-11E5-9242-09173F13E4C5
n5:SMILES
n7:271B5658-363D-11E5-9242-09173F13E4C5
n5:Water-Solubility
n7:271B5652-363D-11E5-9242-09173F13E4C5 n7:271B566A-363D-11E5-9242-09173F13E4C5
n5:logP
n7:271B5650-363D-11E5-9242-09173F13E4C5 n7:271B5653-363D-11E5-9242-09173F13E4C5 n7:271B566C-363D-11E5-9242-09173F13E4C5
n5:logS
n7:271B5651-363D-11E5-9242-09173F13E4C5
n18:hasATCCode
n19:L01XX17
n5:H-Bond-Acceptor-Count
n7:271B5660-363D-11E5-9242-09173F13E4C5
n5:H-Bond-Donor-Count
n7:271B5661-363D-11E5-9242-09173F13E4C5
n5:InChIKey
n7:271B565B-363D-11E5-9242-09173F13E4C5
n5:Polar-Surface-Area--PSA-
n7:271B565C-363D-11E5-9242-09173F13E4C5
n5:Polarizability
n7:271B565E-363D-11E5-9242-09173F13E4C5
n5:Refractivity
n7:271B565D-363D-11E5-9242-09173F13E4C5
n5:Rotatable-Bond-Count
n7:271B565F-363D-11E5-9242-09173F13E4C5
n5:affectedOrganism
Humans and other mammals
n5:casRegistryNumber
119413-54-6
n5:category
n5:containedIn
n6:271B5647-363D-11E5-9242-09173F13E4C5 n6:271B5648-363D-11E5-9242-09173F13E4C5 n6:271B5646-363D-11E5-9242-09173F13E4C5
n5:Bioavailability
n7:271B5666-363D-11E5-9242-09173F13E4C5
n5:Ghose-Filter
n7:271B5668-363D-11E5-9242-09173F13E4C5
n5:MDDR-Like-Rule
n7:271B5669-363D-11E5-9242-09173F13E4C5
n5:Melting-Point
n7:271B566B-363D-11E5-9242-09173F13E4C5
n5:Number-of-Rings
n7:271B5665-363D-11E5-9242-09173F13E4C5
n5:Physiological-Charge
n7:271B5664-363D-11E5-9242-09173F13E4C5
n5:Rule-of-Five
n7:271B5667-363D-11E5-9242-09173F13E4C5
n5:Traditional-IUPAC-Name
n7:271B5655-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-acidic-
n7:271B5662-363D-11E5-9242-09173F13E4C5
n5:pKa--strongest-basic-
n7:271B5663-363D-11E5-9242-09173F13E4C5