| Attributes | Values |
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| rdf:type
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| http://linked.open...gbank/description
| - A pyrimidine nucleoside analogue that inhibits DNA methyltransferase, impairing DNA methylation. It is also an antimetabolite of cytidine, incorporated primarily into RNA. Azacytidine has been used as an antineoplastic agent. [PubChem] (en)
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| http://linked.open...y/drugbank/dosage
| |
| http://linked.open...generalReferences
| - # Cihak A: Biological effects of 5-azacytidine in eukaryotes. Oncology. 1974;30(5):405-22. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/4142650 # Kaminskas E, Farrell AT, Wang YC, Sridhara R, Pazdur R: FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension. Oncologist. 2005 Mar;10(3):176-82. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15793220 # Leone G, Voso MT, Teofili L, Lubbert M: Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS. Clin Immunol. 2003 Oct;109(1):89-102. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/14585280 # Ghoshal K, Bai S: DNA methyltransferases as targets for cancer therapy. Drugs Today (Barc). 2007 Jun;43(6):395-422. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/17612710 # Silverman LR, Demakos EP, Peterson BL, Kornblith AB, Holland JC, Odchimar-Reissig R, Stone RM, Nelson D, Powell BL, DeCastro CM, Ellerton J, Larson RA, Schiffer CA, Holland JF: Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: a study of the cancer and leukemia group B. J Clin Oncol. 2002 May 15;20(10):2429-40. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12011120 # Silverman LR: Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS). Oncologist. 2001;6 Suppl 5:8-14. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/11700387 # Issa JP, Kantarjian H: Azacitidine. Nat Rev Drug Discov. 2005 May;Suppl:S6-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15962522 # O'Dwyer K, Maslak P: Azacitidine and the beginnings of therapeutic epigenetic modulation. Expert Opin Pharmacother. 2008 Aug;9(11):1981-6. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18627335 # Siddiqui MA, Scott LJ: Azacitidine: in myelodysplastic syndromes. Drugs. 2005;65(13):1781-9; discussion 1790-1. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16114977 # Abdulhaq H, Rossetti JM: The role of azacitidine in the treatment of myelodysplastic syndromes. Expert Opin Investig Drugs. 2007 Dec;16(12):1967-75. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/18042004 # Keating GM: Azacitidine: a review of its use in higher-risk myelodysplastic syndromes/acute myeloid leukaemia. Drugs. 2009;69(17):2501-18. doi: 10.2165/11202840-000000000-00000. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19911860 # Sullivan M, Hahn K, Kolesar JM: Azacitidine: a novel agent for myelodysplastic syndromes. Am J Health Syst Pharm. 2005 Aug 1;62(15):1567-73. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16030365 # Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;83(22):11950-8. Epub 2009 Sep 2. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/19726509 (en)
|
| http://linked.open...gy/drugbank/group
| - approved (en)
- investigational (en)
|
| http://linked.open...drugbank/halfLife
| - Mean elimination half-life is approximately 4 hours. (en)
|
| http://linked.open...ugbank/indication
| - For treatment of patients with the following French-American-British myelodysplastic syndrome subtypes: refractory anemia or refractory anemia with ringed sideroblasts (if accompanied by neutropenia or thrombocytopenia or requiring transfusions), refractory anemia with excess blasts, refractory anemia with excess blasts in transformation (now classified as acute myelogenous leukemia with multilineage dysplasia), and chronic myelomonocytic leukemia. (en)
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| http://linked.open...bank/manufacturer
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| sameAs
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| Title
| |
| adms:identifier
| |
| http://linked.open...mechanismOfAction
| - Azacitidine (5-azacytidine) is a chemical analogue of the cytosine nucleoside used in DNA and RNA. Azacitidine is thought to induce antineoplastic activity via two mechanisms; inhibition of DNA methyltransferase at low doses, causing hypomethylation of DNA, and direct cytotoxicity in abnormal hematopoietic cells in the bone marrow through its incorporation into DNA and RNA at high doses, resulting in cell death. As azacitidine is a ribonucleoside, it incoporates into RNA to a larger extent than into DNA. The incorporation into RNA leads to the dissembly of polyribosomes, defective methylation and acceptor function of transfer RNA, and inhibition of the production of protein. Its incorporation into DNA leads to a covalent binding with DNA methyltransferases, which prevents DNA synthesis and subsequent cytotoxicity. (en)
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| http://linked.open...drugbank/packager
| |
| http://linked.open...outeOfElimination
| - Following IV administration of radioactive azacitidine to 5 cancer patients, the cumulative urinary excretion was 85% of the radioactive dose. Fecal excretion accounted for <1% of administered radioactivity over three days. Mean excretion of radioactivity in urine following SC administration of 14C-azacitidine was 50%. (en)
|
| http://linked.open.../drugbank/synonym
| - Azacitidine (en)
- 5 AZC (en)
- Azacytidine (en)
- 5-Azacytidine (en)
- 4-Amino-1-beta-D-ribofuranosyl-S-triazin-2(1H)-one (en)
- Azacitidina (en)
- Azacitidinum (en)
|
| http://linked.open...drugbank/toxicity
| - One case of overdose with azacitidine was reported during clinical trials. A patient experienced diarrhea, nausea, and vomiting after receiving a single IV dose of approximately 290 mg/m2, almost 4 times the recommended starting dose. (en)
|
| http://linked.open...umeOfDistribution
| |
| http://linked.open...ynthesisReference
| - Lorenzo DE FERRA, Maurizio ZENONI, Stefano TURCHETTA, Mauro ANIBALDI, Ettore AMMIRATI, Paolo BRANDI, Giorgio BERARDI, "PROCESS FOR THE SYNTHESIS OF AZACITIDINE AND DECITABINE." U.S. Patent US20110245485, issued October 06, 2011. (en)
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| foaf:page
| |
| http://linked.open...ugbank/IUPAC-Name
| |
| http://linked.open...gy/drugbank/InChI
| |
| http://linked.open...Molecular-Formula
| |
| http://linked.open.../Molecular-Weight
| |
| http://linked.open...noisotopic-Weight
| |
| http://linked.open...y/drugbank/SMILES
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| http://linked.open.../Water-Solubility
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| http://linked.open...ogy/drugbank/logP
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| http://linked.open...ogy/drugbank/logS
| |
| http://linked.open...l/drug/hasATCCode
| |
| http://linked.open...nd-Acceptor-Count
| |
| http://linked.open...-Bond-Donor-Count
| |
| http://linked.open...drugbank/InChIKey
| |
| http://linked.open...urface-Area--PSA-
| |
| http://linked.open...nk/Polarizability
| |
| http://linked.open...bank/Refractivity
| |
| http://linked.open...atable-Bond-Count
| |
| http://linked.open...ugbank/absorption
| - Azacitidine is rapidly absorbed after subcutaneous administration. The bioavailability of subcutaneous azacitidine relative to IV azacitidine is approximately 89%, based on area under the curve. (en)
|
| http://linked.open.../affectedOrganism
| - Humans and other mammals (en)
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| http://linked.open...casRegistryNumber
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| http://linked.open...drugbank/category
| |
| http://linked.open...rugbank/clearance
| |
| http://linked.open...gbank/containedIn
| |
| http://linked.open...k/Bioavailability
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| http://linked.open...bank/Ghose-Filter
| |
| http://linked.open...nk/MDDR-Like-Rule
| |
| http://linked.open...ank/Melting-Point
| |
| http://linked.open...k/Number-of-Rings
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| http://linked.open...siological-Charge
| |
| http://linked.open...bank/Rule-of-Five
| |
| http://linked.open...tional-IUPAC-Name
| |
| http://linked.open...strongest-acidic-
| |
| http://linked.open...-strongest-basic-
| |
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