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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01262
rdf:type
n3:Drug
n3:description
Decitabine is indicated for treatment of patients with myelodysplastic syndrome (MDS). It is a chemical analogue of cytidine, a nucleoside present in DNA and RNA. Cells in the presence of Decitabine incorporate it into DNA during replication and RNA during transcription. The incorporation of Decitabine into DNA or RNA inhibits methyltransferase thereby causing demethylation in that sequence. This adversely affects the way that cell regulatory proteins are able to bind to the DNA/RNA substrate.
n3:dosage
n9:271B60A7-363D-11E5-9242-09173F13E4C5 n9:271B60A8-363D-11E5-9242-09173F13E4C5 n9:271B60A9-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Appleton K, Mackay HJ, Judson I, Plumb JA, McCormick C, Strathdee G, Lee C, Barrett S, Reade S, Jadayel D, Tang A, Bellenger K, Mackay L, Setanoians A, Schatzlein A, Twelves C, Kaye SB, Brown R: Phase I and pharmacodynamic trial of the DNA methyltransferase inhibitor decitabine and carboplatin in solid tumors. J Clin Oncol. 2007 Oct 10;25(29):4603-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17925555 # Wijermans PW, Ruter B, Baer MR, Slack JL, Hussain SI, Lubbert M: Efficacy of decitabine in the treatment of patients with chronic myelomonocytic leukemia (CMML). Leuk Res. 2007 Sep 17;. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17881052 # Daskalakis M, Blagitko-Dorfs N, Hackanson B: Decitabine. Recent Results Cancer Res. 2010;184:131-57. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20072836 # Saba HI, Wijermans PW: Decitabine in myelodysplastic syndromes. Semin Hematol. 2005 Jul;42(3 Suppl 2):S23-31. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16015501 # Jabbour E, Issa JP, Garcia-Manero G, Kantarjian H: Evolution of decitabine development: accomplishments, ongoing investigations, and future strategies. Cancer. 2008 Jun;112(11):2341-51. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18398832 # Stresemann C, Lyko F: Modes of action of the DNA methyltransferase inhibitors azacytidine and decitabine. Int J Cancer. 2008 Jul 1;123(1):8-13. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18425818 # Oki Y, Aoki E, Issa JP: Decitabine--bedside to bench. Crit Rev Oncol Hematol. 2007 Feb;61(2):140-52. Epub 2006 Oct 4. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17023173
n3:group
approved investigational
n3:halfLife
The terminal phase elimination half-life is 0.51 ± 0.31 hours.
n3:indication
For treatment of patients with myelodysplastic syndromes (MDS) including previously treated and untreated, de novo and secondary MDS of all French-American-British subtypes (refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia) and intermediate-1, intermediate-2, and high-risk International Prognostic Scoring System groups (scores ≥0.5).
owl:sameAs
n6:DB01262 n23:DB01262
dcterms:title
Decitabine
adms:identifier
n11:451668 n12:46505657 n13:PA164749631 n14:Decitabine n17:50131 n18:D03665 n19:62856-600-01 n20:397844 n21:DB01262
n3:mechanismOfAction
Decitabine is believed to exert its antineoplastic effects following its conversion to decitabine triphosphate, where the drug directly incorporates into DNA and inhibits DNA methyltransferase, the enzyme that is responsible for methylating newly synthesized DNA in mammalian cells. This results in hypomethylation of DNA and cellular differentiation or apoptosis. Decitabine inhibits DNA methylation in vitro, which is achieved at concentrations that do not cause major suppression of DNA synthesis. Decitabine-induced hypomethylation in neoplastic cells may restore normal function to genes that are critical for the control of cellular differentiation and proliferation. In rapidly dividing cells, the cytotoxicity of decitabine may also be attributed to the formation of covalent adducts between DNA methyltransferase and decitabine that has been incorporated into DNA. Non-proliferating cells are relatively insensitive to decitabine. Decitabine is cell cycle specific and acts peripherally in the S phase of the cell cycle. It does not inhibit the progression of cells from the G1 to S phase.
n3:packager
n22:271B60A4-363D-11E5-9242-09173F13E4C5 n22:271B60A5-363D-11E5-9242-09173F13E4C5 n22:271B60A3-363D-11E5-9242-09173F13E4C5
n3:synonym
5-aza-2'-deoxycytidine Decitabine 5-Azadeoxycytidine Azadc Dezocitidine 4-amino-1-(2-Deoxy-beta-D-erythro-pentofuranosyl)-S-triazin-2(1H)-one
n3:toxicity
There is no known antidote for overdosage with decitabine. Higher doses are associated with increased myelosuppression including prolonged neutropenia and thrombocytopenia.
n3:proteinBinding
Plasma protein binding of decitabine is negligible (<1%).
n3:synthesisReference
Julian Paul Henschke, Xiaoheng Zhang, Jianbo Yu, Kun Hu, Lijun Mei, "Synthesis of Decitabine." U.S. Patent US20100087637, issued April 08, 2010.
n26:hasConcept
n27:M0062824
foaf:page
n8:decitabine.html
n3:IUPAC-Name
n4:271B60AE-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B60B4-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B60B3-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B60B0-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B60B1-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B60B2-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B60AC-363D-11E5-9242-09173F13E4C5 n4:271B60C4-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B60AA-363D-11E5-9242-09173F13E4C5 n4:271B60AD-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B60AB-363D-11E5-9242-09173F13E4C5
n15:hasATCCode
n16:L01BC08
n3:H-Bond-Acceptor-Count
n4:271B60BA-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B60BB-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B60B5-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B60B6-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B60B8-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B60B7-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B60B9-363D-11E5-9242-09173F13E4C5
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
2353-33-5
n3:category
n3:clearance
* 125 L/h/m2 [Patients receiving 15 mg/m2 3-hr infusion every 8 hours for 3 days] * 210 L/h/m2 [20 mg/m2 1-hr infusion daily for 5 days]
n3:containedIn
n25:271B60A6-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B60C0-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B60C2-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B60C3-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B60BF-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B60BE-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B60C1-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B60AF-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B60BC-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B60BD-363D-11E5-9242-09173F13E4C5