azacitidine

ladakamycin

CAS: 320-67-2 C8 H12 N4 O5 MW: 244.20764000

Identification

Nameazacitidine
IUPAC4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
CAS Number320-67-2
EINECS206-280-2
FDA UNIIM801H13NRU
Molecular FormulaC8 H12 N4 O5
Molecular Weight244.20764000
MDL NumberMFCD00006539
Nikkaji NumberJ1.523G
Beilstein0620461
XlogP3-2.20 (est)

Regulatory

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)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-bird - wild LD50 100 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorypharmaceuticals / chemical synthisis
Recommendation for azacitidine usage levels up tonot for fragrance use.
Recommendation for azacitidine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

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-aza cytidine aza cytidine, 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- 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. 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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. 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