5-Aza-2'-deoxycytidine

5-Aza-2'-deoxycytidine Basic information
Indications and Usage Mechanisms of Action Side Effects Category Toxicity grading Acute toxicity Flammability Hazardous characteristics Storage characteristics Fire extinguishing agent
Product Name:5-Aza-2'-deoxycytidine
Synonyms:4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one;5-Aza-2'-deoxycytidine,98+%;4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one;Decitabine(NSC127716);4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-s-triazin-2(1h)-on;4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-s-triazin-2(1h)-one;5-azadeoxycytidine;5-triazin-2(1h)-one,4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-3
CAS:2353-33-5
MF:C8H12N4O4
MW:228.21
EINECS:219-089-4
Product Categories:Inhibitors;Deoxycytidine;API;Bases & Related Reagents;Nucleotides;Anti-cancer&immunity;analog of cytosine;Intermediates & Fine Chemicals;Pharmaceuticals;Epigenetics;Inhibitor;2353-33-5
Mol File:2353-33-5.mol
5-Aza-2'-deoxycytidine Structure
5-Aza-2'-deoxycytidine Chemical Properties
Melting point ~200 °C (dec.)
alpha D22 +68.5° (30 min) +57.8° (6 hr) (c = 0.5 in water)
Boiling point 370.01°C (rough estimate)
density 1.3771 (rough estimate)
refractive index 1.6590 (estimate)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility acetic acid/water (1:1): 50 mg/mL
pka14.02±0.60(Predicted)
form Powder
color White to Off-white
Merck 14,2853
BRN 617982
Stability:Stable. May be light or air sensitive. Incompatible with strong oxidizing agents.
InChIKeyXAUDJQYHKZQPEU-KVQBGUIXSA-N
CAS DataBase Reference2353-33-5(CAS DataBase Reference)
EPA Substance Registry System5-Aza-2'-deoxycytidine (2353-33-5)
Safety Information
Hazard Codes Xn,Xi,T
Risk Statements 22-36/37/38-68-61
Safety Statements 26-36-36/37
WGK Germany 3
RTECS XZ3012000
10-34
HS Code 29349990
ToxicityLD50 in mice (mg/kg): 190 i.p. (Momparler, 1985)
MSDS Information
ProviderLanguage
5-Aza-2'-deoxycytidine English
SigmaAldrich English
5-Aza-2'-deoxycytidine Usage And Synthesis
Indications and Usage5-Aza-2’-deoxycytidine, also known as decitabine or 2'-deoxy-5-azacytidine, is a cell cycle S phase-specific drug used to treat myelodysplastic syndromes (MDS.)
Mechanisms of ActionDemethylating agents can regulate gene expression by activating tumor suppressor genes and enhancing the differentiation of genes, which help treat MDS. 5-Aza-2’-deoxycytidine is a natural andenosine analogue of 2′-deoxycytidine, known to the be strongest methylation specific inhibitor of DNA. After phosphorylation it can inhibit DNA methyltransferase, reducing DNA methylation, leading to demethylation of tumor cells, which can restore the normal functioning of genes, thus inhibiting tumor cell proliferation and preventing the occurrence of drug resistance. 5-Aza-2’-deoxycytidine inhibits DNA methylation in vitro, but does not affect its synthesis. Moreover, non-proliferating cells are not sensitive to it. 5-Aza-2’-deoxycytidine has anti-tumor activity and is characterized by a dual mechanism based on dose differences. At high concentrations it is cytoxic, while at low concentrations it is demethlyating.
Side Effects
  • Neutropenia, thrombocytopenia, anemia, vomiting, fatigue, fever, cough, nausea, constipation, diarrhea, hyperglycemia, and heat induced neutrophil.
  • Large doses may cause neurotoxicity, manifested as lethargy, aphasia, hemiplegia, etc., which disappears after stopping.
Categorytoxic substance
Toxicity gradinghigh
Acute toxicityIntravenous – mouse LD50: 22 mg/kg; peritoneal – mouse LD50: 190 mg/kg
Flammability Hazardous characteristicsCombustible; produces toxic nitrogen oxide fumes.
Storage characteristicsVentilated, cold, and dry; store away from raw food materials.
Fire extinguishing agentdry powder, foam, sand, carbon dioxide, water mist.
DescriptionDecitabine, 5-aza-2’-deoxycytidine, has been launched for the treatment of myelodysplastic syndromes (MDS). MDS are a set of hematologic disorders affecting the bone marrow that result in ineffective formation and development of blood cells. Furthermore, patients with MDS have a high risk of progressing to acute myeloid leukemia (AML). Traditional treatments include blood transfusions, hematopoietic growth factors, and prophylactic antibiotics, but these measures merely improve the quality of life with questionable effects on disease modification. While stem-cell transplantation is an aggressive, potentially curative approach, the advanced age or the other complicating health issues of most patients preclude them from considering this option. Recent advances in the underlying etiology of MDS, however, have led to the development of a new class of compounds known as ‘‘demethylating agents’’. Decitabine follows the successful introduction of the first DNA methyltransferase inhibitor azacitidine.
Chemical Propertieswhite crystalline powder
OriginatorPharmachemie (Netherlands)
Uses5-Aza-2′-deoxycytidine has been used as a demethylating agent in breast cancer cell line, chromatin, DNA and promoter region of p16 gene.
UsesUsed as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines.
UsesDecitabine is a potent inhibitor of DNA methylation with IC50 of 438 nM and 4.38 nM in HL-60 and KG1a cells, respectively
DefinitionChEBI: 5-aza-2'-deoxycytidine is a 2'-deoxyribonucleoside.
Brand nameDacogen (Millot Laboratories, France).
General DescriptionFine white crystalline powder. Used as a drug.
Air & Water ReactionsProbably light and air sensitive. Water soluble. Decomposes in aqueous solution at a rate that depends on pH: at pH 7 the drug is more stable than at pH 9, but is less stable than at pH 6. At pH 7 and 99°F, approximately 7% conversion occurs in 1 hour .
Reactivity Profile5-Aza-2'-deoxycytidine is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
Fire HazardFlash point data for 5-Aza-2'-deoxycytidine are not available. 5-Aza-2'-deoxycytidine is probably combustible.
Biological ActivityCytosine analog that once incorporated into DNA acts as a suicide substrate for DNA methyltransferase. Inhibits DNA methyltransferase and results in DNA hypomethylation and activation of silent genes. Chemotherapeutic agent; suppresses growth of human tumor cell lines. Demethylates differentiation-related genes; reverses embryonic stem cell differentiation.
Biochem/physiol ActionsPrimary TargetDNA methyltransferase inhibitor
Clinical UseAntineoplastic antimetabolite agent:
Treatment of acute myeloid leukaemia
Safety ProfilePoison by intravenous route.Human mutation data reported. When heated todecomposition it emits toxic fumes of NOx.
SynthesisSilylated 5-aza-cytosine (28) was condensed with 9- fluorenylmethoxycarbonyl (Fmoc) protected 2-deoxy-1-chlororibose (27) with tin chloride (IV) in dichloroethane (Scheme 4). The coupled product 29 was de-protected with excess triethylamine in dry pyridine to give decitabine (IV) in 36% yield after separation from its corresponding |áisomer.

Synthesis_2353-33-5

targetTelomerase | DNA Methyltransferase | p21
Drug interactionsPotentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine, increased risk of agranulocytosis.
MetabolismThe exact route of metabolism and elimination is unknown but thought to be through deamination by cytidine deaminase in the liver, kidney, intestinal epithelium and blood to form inactive metabolites.
storage+4°C
References1) Bender et al. (1998), Inhibition of DNA methylation by 5-aza-2′-deoxycytidine suppresses the growth of human tumor cell lines; Cancer Res., 58 95 2) El-Serafi et al. (2011), Epigenetic modifiers influence lineage commitment of human bone marrow stromal cells: Differential effects of 5-aza-deoxycytidine and trichostatin A; Differentiation, 81 35
5-Aza-2'-deoxycytidine Preparation Products And Raw materials
Cytidine-5'-triphosphate disodium salt dihydrate Cytidine 5’-monophosphate Floxuridine Cytosine ALTRENOGEST 5-Azacytidine 6-Aminocaproic acid Glycine 5-Aza-2'-deoxycytidine Cytarabine 5-Azacytosine Fluorocytosine 2'-Deoxycytidine monohydrate Cytidine Tris(hydroxymethyl)aminomethane AMINO ACIDS 3-Aminophenol 5-Fluorocytidine

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