EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

azacitidine
ladakamycin

Supplier Sponsors

Name:4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
CAS Number: 320-67-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:206-280-2
FDA UNII: M801H13NRU
Nikkaji Web:J1.523G
Beilstein Number:0620461
MDL:MFCD00006539
XlogP3:-2.20 (est)
Molecular Weight:244.20764000
Formula:C8 H12 N4 O5
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:pharmaceuticals / chemical synthisis
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Appearance:WHITE crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 229.00 °C. @ 760.00 mm Hg
Boiling Point: 534.46 °C. @ 760.00 mm Hg (est)
Flash Point: 531.00 °F. TCC ( 277.00 °C. ) (est)
logP (o/w): -2.191 (est)
Soluble in:
 water, 8.894e+004 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
5-Azacytidine >98%
Odor: characteristic
Use: Azacitidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases.
Changzhou Longo Chemical
5-Azacytidine
George Uhe Company
5-Azacytidine
Glentham Life Sciences
5-Azacytidine
Santa Cruz Biotechnology
For experimental / research use only.
5-Azacytidine ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
5-Azacytidine ≥98% (HPLC)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-bird - wild LD50 100 mg/kg
Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.

intravenous-dog LD50 7200 ug/kg
BLOOD: OTHER CHANGES
Advances in Pharmacology and Chemotherapy. Vol. 14, Pg. 285, 1977.

intraperitoneal-mouse LD50 68 mg/kg
Experientia. Vol. 22, Pg. 53, 1966.

intravenous-mouse LD50 229 mg/kg
BEHAVIORAL: ATAXIA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Technical Information Service. Vol. PB84-211432

oral-mouse LD50 572 mg/kg
Toxicology and Applied Pharmacology. Vol. 19, Pg. 382, 1971.

oral-quail LD50 > 100 mg/kg
Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
pharmaceuticals / chemical synthisis
Recommendation for azacitidine usage levels up to:
 not for fragrance use.
 
Recommendation for azacitidine flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9444
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
Chemidplus:0000320672
EPA/NOAA CAMEO:hazardous materials
RTECS:XZ3017500 for cas# 320-67-2
 
References:
 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9444
Pubchem (sid):134975625
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C11262
HMDB (The Human Metabolome Database):HMDB15063
Export Tariff Code:2933.69.0050
MedlinePlusSupp:View
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 not found in nature
 
Synonyms:
4-amino-1-(b-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,3,5-triazin-2(1H)-one
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one
4-amino-1-b-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
 azacitidinum
 azacytidine
5-azacytidine
azacytidine, 5-
1-[(4S,2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-amino-1,3,5-triazin-2-one
 ladakamycin
 mylosar
1,3,5-triazin-2(1H)-one, 4-amino-1-b-D-ribofuranosyl-
 

Articles:

PubMed:Pharmacokinetics of different formulations of oral azacitidine (CC-486) and the effect of food and modified gastric pH on pharmacokinetics in subjects with hematologic malignancies.
PubMed:Blastic plasmacytoid dendritic cell neoplasm: the first report of two cases treated by 5-azacytidine.
PubMed:Efficacy and tolerability of treatment with azacitidine for 5 days in elderly patients with acute myeloid leukemia.
PubMed:Azacitidine in the management of patients with myelodysplastic syndromes.
PubMed:FDA drug approval summary: azacitidine (5-azacytidine, Vidaza) for injectable suspension.
PubMed:Impact of TET2 mutations on response rate to azacitidine in myelodysplastic syndromes and low blast count acute myeloid leukemias.
PubMed:Induction of proto-oncogene BRF2 in breast cancer cells by the dietary soybean isoflavone daidzein.
PubMed:Chronic myelomonocytic leukemia: 2013 update on diagnosis, risk stratification, and management.
PubMed:The demethylating agent 5-Aza reduces the growth, invasiveness, and clonogenicity of uveal and cutaneous melanoma.
PubMed:Lower gastric secretion and higher incorporation of orotic acid into liver RNA in rats treated with 5-azacytidine and cycloheximide.
PubMed:Subchronic oral toxicity study of decitabine in combination with tetrahydrouridine in CD-1 mice.
PubMed:Vitamin A and beta-carotene inhibitory effect during 1,2-dimethylhydrazine induced hepatocarcinogenesis potentiated by 5-azacytidine.
PubMed:Inhibition of aflatoxin metabolism and growth of Aspergillus flavus in liquid culture by a DNA methylation inhibitor.
PubMed:Decitabine induces delayed reactive oxygen species (ROS) accumulation in leukemia cells and induces the expression of ROS generating enzymes.
PubMed:Epigenetic action of decitabine (5-aza-2'-deoxycytidine) is more effective against acute myeloid leukemia than cytotoxic action of cytarabine (ARA-C).
PubMed:Can hypomethylating agents provide a platform for curative therapy in myelodysplastic syndromes?
PubMed:Chemical induction of endogenous retrovirus particles from the vero cell line of African green monkeys.
PubMed:Approval summary: azacitidine for treatment of myelodysplastic syndrome subtypes.
PubMed:Development of phenotypic screening assays for γ-globin induction using primary human bone marrow day 7 erythroid progenitor cells.
PubMed:Activity of decitabine in patients with myelodysplastic syndrome previously treated with azacitidine.
PubMed:Advances in myelodysplastic syndrome: nursing implications of azacitidine.
PubMed:Boulevard of broken dreams: drug approval for older adults with acute myeloid leukemia.
PubMed:Chronic myelomonocytic leukemia: 2012 update on diagnosis, risk stratification, and management.
PubMed:Reexpression of tumor suppressor, sFRP1, leads to antitumor synergy of combined HDAC and methyltransferase inhibitors in chemoresistant cancers.
PubMed:Azacitidine-associated hyperthermia and interstitial pneumonitis in a patient with myelodysplastic syndrome.
PubMed:Reprogramming of pig dermal fibroblast into insulin secreting cells by a brief exposure to 5-aza-cytidine.
PubMed:The NuRD complex cooperates with DNMTs to maintain silencing of key colorectal tumor suppressor genes.
PubMed:Colon cancer cell apoptosis is induced by combined exposure to the n-3 fatty acid docosahexaenoic acid and butyrate through promoter methylation.
PubMed:DNA demethylation and invasive cancer: implications for therapeutics.
PubMed:Epigenetic potentiation of NY-ESO-1 vaccine therapy in human ovarian cancer.
PubMed:Folate deficiency induces dysfunctional long and short telomeres; both states are associated with hypomethylation and DNA damage in human WIL2-NS cells.
PubMed:Economic analysis of decitabine versus best supportive care in the treatment of intermediate- and high-risk myelodysplastic syndromes from a US payer perspective.
PubMed:Discovery of drugs that possess activity against feline leukemia virus.
PubMed:Expression and immunotherapeutic targeting of the SSX family of cancer-testis antigens in prostate cancer.
PubMed:MutS HOMOLOG1-derived epigenetic breeding potential in tomato.
PubMed:Current status of epigenetic treatment in myelodysplastic syndromes.
PubMed:Silencing of Wnt5a during colon cancer metastasis involves histone modifications.
PubMed:Developmental toxicity and psychotoxicity of potassium iodide in rats: a case for the inclusion of behaviour in toxicological assessment.
PubMed:Pharmacotherapy of myelodysplastic syndromes.
PubMed:Current and novel therapeutic approaches in myelodysplastic syndromes.
PubMed:DNA methyltransferases as targets for cancer therapy.
PubMed:Myelodysplastic Syndromes: Diagnosis and Treatment.
PubMed:Use of hypomethylating agents in myelodysplastic syndromes.
PubMed:Allele-specific, age-dependent and BMI-associated DNA methylation of human MCHR1.
PubMed:Epigenetics and oncology.
PubMed:Epigenetic drugs against cancer: an evolving landscape.
PubMed:MDS: Refining existing therapy through improved biologic insights.
PubMed:DNA methylation and soy phytoestrogens: quantitative study in DU-145 and PC-3 human prostate cancer cell lines.
PubMed:Character of the stimulatory response of uridine kinase in rat livers to cycloheximide treatment.
PubMed:Multicenter study of decitabine administered daily for 5 days every 4 weeks to adults with myelodysplastic syndromes: the alternative dosing for outpatient treatment (ADOPT) trial.
PubMed:Early detection of endogenous retroviruses in chemically induced mouse cells.
PubMed:Epigenetic regulation of reelin and brain-derived neurotrophic factor genes in long-term potentiation in rat medial prefrontal cortex.
PubMed:DZNep is a global histone methylation inhibitor that reactivates developmental genes not silenced by DNA methylation.
PubMed:Effects of specific DNMT gene depletion on cancer cell transformation and breast cancer cell invasion; toward selective DNMT inhibitors.
PubMed:Optimal sequencing of treatments for patients with myelodysplastic syndromes.
PubMed:Myc sensitizes p53-deficient cancer cells to the DNA-damaging effects of the DNA methyltransferase inhibitor decitabine.
PubMed:Phase I clinical trial of oral rigosertib in patients with myelodysplastic syndromes.
PubMed:DNA methyltransferase inhibitors in acute myeloid leukemia: discovery, design and first therapeutic experiences.
PubMed:Lycopene and apo-10'-lycopenal do not alter DNA methylation of GSTP1 in LNCaP cells.
PubMed:Decitabine.
PubMed:Pharmacological induction of fetal hemoglobin: Why haven't we been more successful in thalassemia?
PubMed:Risk-based management of myelodysplastic syndrome.
PubMed:Decitabine and its role in the treatment of hematopoietic malignancies.
PubMed:Developmental toxicity and psychotoxicity of sodium nitrite in rats.
PubMed:Delivery of 5-aza-2'-deoxycytidine to cells using oligodeoxynucleotides.
PubMed:New treatment for rare bone marrow condition.
PubMed:Hematopoietic growth factors in myelodysplastic syndromes.
PubMed:Regulatory approvals of pediatric oncology drugs: previous experience and new initiatives.
PubMed:New approaches to the treatment of myelodysplasia.
PubMed:DNA methylation and cancer therapy: new developments and expectations.
PubMed:How much? How frequent? How long? A clinical guide to new therapies in myelodysplastic syndromes.
PubMed:Epigenetics: the role of methylation in the mechanism of action of tumor suppressor genes.
PubMed:Salmonella typhimurium strain TA100 differentiates several classes of carcinogens and mutagens by base substitution specificity.
PubMed:Future directions in myelodysplastic syndrome: newer agents and the role of combination approaches.
PubMed:Azacytidine (Vidaza(R)) in the treatment of myelodysplastic syndromes.
PubMed:Treatment strategies to optimize clinical benefit in the patient with myelodysplastic syndromes.
PubMed:Acute myeloid leukemia and myelodysplastic syndromes in older patients.
PubMed:Targeted therapies in myelodysplastic syndrome.
PubMed:Antiangiogenic therapy in myelodysplastic syndromes: is there a role?
PubMed:Novel agents for the management of myelodysplastic syndromes.
 
Notes:
a pyrimidine 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.
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