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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01008
rdf:type
n3:Drug
n3:description
Busulfan is a bifunctional alkylating agent, having a selective immunosuppressive effect on bone marrow. It is not a structural analog of the nitrogen mustards. It has been used in the palliative treatment of chronic myeloid leukemia (myeloid leukemia, chronic), but although symptomatic relief is provided, no permanent remission is brought about. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), busulfan is listed as a known carcinogen. [PubChem]
n3:dosage
n29:271B5034-363D-11E5-9242-09173F13E4C5 n29:271B5035-363D-11E5-9242-09173F13E4C5 n29:271B5036-363D-11E5-9242-09173F13E4C5 n29:271B5037-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Lesurtel M, Graf R, Aleil B, Walther DJ, Tian Y, Jochum W, Gachet C, Bader M, Clavien PA: Platelet-derived serotonin mediates liver regeneration. Science. 2006 Apr 7;312(5770):104-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16601191 # Valdez BC, Andersson BS: Interstrand crosslink inducing agents in pretransplant conditioning therapy for hematologic malignancies. Environ Mol Mutagen. 2010 Jul;51(6):659-68. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20577993 # Hall AG, Tilby MJ: Mechanisms of action of, and modes of resistance to, alkylating agents used in the treatment of haematological malignancies. Blood Rev. 1992 Sep;6(3):163-73. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/1422285 # Ciurea SO, Andersson BS: Busulfan in hematopoietic stem cell transplantation. Biol Blood Marrow Transplant. 2009 May;15(5):523-36. Epub 2009 Feb 12. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19361744 # McCune JS, Holmberg LA: Busulfan in hematopoietic stem cell transplant setting. Expert Opin Drug Metab Toxicol. 2009 Aug;5(8):957-69. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19611402 # Krivoy N, Hoffer E, Lurie Y, Bentur Y, Rowe JM: Busulfan use in hematopoietic stem cell transplantation: pharmacology, dose adjustment, safety and efficacy in adults and children. Curr Drug Saf. 2008 Jan;3(1):60-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18690982 # Nath CE, Shaw PJ: Busulphan in blood and marrow transplantation: dose, route, frequency and role of therapeutic drug monitoring. Curr Clin Pharmacol. 2007 Jan;2(1):75-91. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18690856 # FDA label
n3:group
approved investigational
n3:halfLife
2.6 hours
n3:indication
For use in combination with cyclophosphamide as a conditioning regimen prior to allogeneic hematopoietic progenitor cell transplantation for chronic myelogenous (myeloid, myelocytic, granulocytic) leukemia (FDA has designated busulfan as an orphan drug for this use). It is also used as a component of pretransplant conditioning regimens in patients undergoing bone marrow transplantation for acute myeloid leukemia and nonmalignant diseases.
n3:manufacturer
n26:271B5030-363D-11E5-9242-09173F13E4C5 n26:271B5031-363D-11E5-9242-09173F13E4C5
owl:sameAs
n25:DB01008 n30:DB01008
dcterms:title
Busulfan
adms:identifier
n7:Busulfan n8:2384 n9:DB01008 n12:28901 n13:67286-0054-2 n15:PA448691 n16:D00248 n20:2478 n21:46506234
n3:mechanismOfAction
Busulfan is an alkylating agent that contains 2 labile methanesulfonate groups attached to opposite ends of a 4-carbon alkyl chain. Once busulfan is hydrolyzed, the methanesulfonate groups are released and carbonium ions are produced. These carbonium ions alkylate DNA, which results in the interference of DNA replication and RNA transcription, ultimately leading to the disruption of nucleic acid function. Specifically, its mechanism of action through alkylation produces guanine-adenine intrastrand crosslinks. This occurs through an SN2 reaction in which the relatively nucleophilic guanine N7 attacks the carbon adjacent to the mesylate leaving group. This kind of damage cannot be repaired by cellular machinery and thus the cell undergoes apoptosis.
n3:packager
n26:271B502E-363D-11E5-9242-09173F13E4C5 n26:271B502F-363D-11E5-9242-09173F13E4C5 n26:271B502D-363D-11E5-9242-09173F13E4C5
n3:patent
n5:5430057
n3:routeOfElimination
Following administration of 14C- labeled busulfan to humans, approximately 30% of the radioactivity was excreted into the urine over 48 hours; negligible amounts were recovered in feces. Less than 2% of the administered dose is excreted in the urine unchanged within 24 hours. Elimination of busulfan is independent of renal function.
n3:synonym
Myleran Misulban 1,4-Bis(methanesulfonoxy)butane Mablin Myeloleukon Tetramethylene bis(methanesulfonate) 1,4-Dimesyloxybutane Mitostan Busulfano 1,4-Butanediol dimethanesulfonate Leucosulfan Busulfan 1,4-Dimethanesulfonoxybutane Bisulfex Busulfanum Mielucin
n3:toxicity
Signs of overdose include allergic reaction, unusual bleeding or bruising, sudden weakness or unusual fatigue, persistent cough, congestion, or shortness of breath; flank, stomach or joint pain; pronounced nausea, vomiting, diarrhea, dizziness, confusion, or darkening of the skin, chills, fever, collapse, and loss of consciousness.
n17:hasAHFSCode
n19:10-00-00
n3:foodInteraction
Take without regard to meals. Drink liberally.
n3:proteinBinding
32% bound to plasma proteins and 47% bound to red blood cells.
n3:synthesisReference
Timmis, G.M.; U S . Patent 2,917,432; December 15, 1959; assigned to Burroughs Wellcome & Co., Inc.
n10:hasConcept
n11:M0003079
foaf:page
n23:busulfan.html n27:busulfan.htm
n3:IUPAC-Name
n4:271B503C-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5042-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5041-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B503E-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B503F-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5040-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5050-363D-11E5-9242-09173F13E4C5 n4:271B503A-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5052-363D-11E5-9242-09173F13E4C5 n4:271B5038-363D-11E5-9242-09173F13E4C5 n4:271B503B-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5039-363D-11E5-9242-09173F13E4C5
n17:hasATCCode
n18:L01AB01
n3:H-Bond-Acceptor-Count
n4:271B5048-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5049-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5043-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5044-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5046-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5045-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5047-363D-11E5-9242-09173F13E4C5
n3:absorption
Completely absorbed from the gastrointestinal tract. Busulfan is a small, highly lipophilic molecule that crosses the blood-brain-barrier. The absolute bioavailability, if a single 2 mg IV bolus injection is given to adult patients, is 80% ± 20%. In children (1.5 - 6 years old), the absolute bioavailability was 68% ± 31%. When a single oral dose is given to patients, the area under the curve (AUC) was 130 ng•hr/mL. The peak plasma concentration when given orally is 30 ng/mL (after dose normalization to 2 mg). It takes 0.9 hours to reach peak plasma concentration after dose normalization to 4 mg.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
55-98-1
n3:category
n3:clearance
* 2.52 ml/min/kg [Following an infusion of dose of 0.8 mg/kg every six hours, for a total of 16 doses over four days]
n3:containedIn
n28:271B5033-363D-11E5-9242-09173F13E4C5 n28:271B5032-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B504C-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B504E-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B504F-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5051-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B504B-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B504A-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B504D-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B503D-363D-11E5-9242-09173F13E4C5