CAS Number320-67-2
SynonymsVidaza; EINECS 206-280-2; 5 AZC; 4-Amino-1-b-D-ribofuranosyl-1,3,5-triazine-2(1H)-one; 5-AZCR; 5'-azacytidine; azacytidine; Ladakamycin; Azacitidine; AzGR; 5-Azacytidine; 5-AC; 4-amino-1-(b-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; 5-AC-15N4; 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; L-β-Ribofuranosyl-5-azacytosine; 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-on; mylosar; MFCD00006539; 5-AZAC
Molecular FormulaC8H12N4O5
Molecular Weight244.20
Purity≥98 (HPLC)%
Density2.1±0.1 g/cm3
Boiling Point534.5±60.0 °C at 760 mmHg
Melting Point226-232 °C (dec.) (lit.)
Appearancepowder
EINECS206-280-2
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 320-67-2 |
| Catalog No. | 2A-0200398 |
| Chinese Name | 阿扎胞苷 |
| Synonyms | Vidaza; EINECS 206-280-2; 5 AZC; 4-Amino-1-b-D-ribofuranosyl-1,3,5-triazine-2(1H)-one; 5-AZCR; 5'-azacytidine; azacytidine; Ladakamycin; Azacitidine; AzGR; 5-Azacytidine; 5-AC; 4-amino-1-(b-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; 5-AC-15N4; 4-Amino-1-(β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; L-β-Ribofuranosyl-5-azacytosine; 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-on; mylosar; MFCD00006539; 5-AZAC |
| Molecular Formula | C8H12N4O5 |
| Molecular Weight | 244.20 |
| Purity | ≥98 (HPLC) |
| Density | 2.1±0.1 g/cm3 |
| Boiling Point | 534.5±60.0 °C at 760 mmHg |
| Melting Point | 226-232 °C (dec.) (lit.) |
| Appearance | powder |
| Water Solubility | 0.5-1.0 g/100 mL at 21 ºC |
| Storage Condition | Store dry at 4℃. |
| Application | 5-Azacytidine is a nucleoside analog of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. |
| EINECS | 206-280-2 |
| HTC | 2934999090 |
| PubChem ID | 24278211 |
| MDL Number | MFCD00006539 |
| SMILES | NC1=NC(=O)N(C=N1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O |
| InChI | 1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1 |
| InChI Key | NMUSYJAQQFHJEW-KVTDHHQDSA-N |
| Beilstein/REAXYS | 620461 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | Transport |
| Risk Codes | R45;R46;R22 |
| Safety Description | S53;S22;S36/37/39;S45 |
| MSDS | msds/6291_1_320_67_2.pdf |
| Bioactivity | 5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Epigenetics >> DNA Methyltransferase Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer Target DNMT1 Nucleoside Antimetabolite/Analog Autophagy In Vitro Unmethylated CpG islands associated with a variety of genes become partially or fully methylated in tumors and can be reactivated by 5-Azacytidine[1]. 5-Azacytidine acts as weak inducers of erythroid differentiation of Friend erythroleukemia cells in the same concentration range where they affect DNA methyltransferase activity[2]. 5-Azacytidine inhibits L1210 cells with ID50 and ID90 values of 0.019 and circa 0.15 μg/mL, respectively[3]. In Vivo TdR-3H incorporation is significantly inhibited when the animals are exposed to 5-Azacitidine (100 mg/kg, i.p.) for 2 hr or longer[3]. Kinase Assay A crude cell-free extract is isolated from LI 210 cells in culture by suspension of the cells in a given volume of 0.05mol/LTris-HCl buffer, pH 7.4, and sonic extraction with a Biosonik at 70% maximal output for 30 sec. The supernatant is collected after centrifugation at 105,000 × g for 60 min (4°C) in a Model L Spinco ultracentrifuge. The final protein concentration of the cell-free extracts is approximately 3 mg/mL. The extracts are used as the source of enzymes. Ribonucleotide reductase activity is measured. A unit of enzyme is defined as the amount that catalyzed dCMP synthesis at a rate of 1 mμmole/hr. The assay systems for the measurement of pyrimidine nucleoside (CR) and deoxynucleoside (TdR, CdR) kinases are essentially those described by Chu and Fischer. However, reactions are terminated by heating for 2 min in a boiling water bath, and the phosphorylated derivatives are isolated according to the method of Bach. Fifty-jul aliquots are applied to 1-inch discs of diethylaminoethyl paper, which are then placed in counting vials and eluted with 0.5 mL of 0.5 mol/LPCA. After 1 hr, 12 mL of Diotol are added, and the radioactivity is determined. Cell Assay Twenty mL of cells (circa 1×104 cells/mL) are pipetted into sterilized culture tubes with screw caps and incubated at 37°C overnight. The experiment is initiated by the addition of 1 mL of 5-Azacytidine (5-azaCR) or medium for a given period (from 0 to 240 min) prior to the addition of 1 mL of metabolite (or medium). Cell growth is determined twice a day for 3 days by means of a Model A Coulter counter. To determine IDSO and ID90 values, 5 mL of L1210 cells (5×103 cells/mL) are incubated with the drug at 37°C for 3 days, and cell growth is determined. Animal Admin For the in vivo experiments, leukemic mice (bearing circa 1×103 cells/animal) are given injections i.p. with 0.2 mL of 5-Azacytidine (5-azaCR) of a given concentration. Two hr later, the reaction is started by injecting 0.5 mL of labeled metabolite (TdR-3H or UR-3H, 10 /μCi/12.5 μg). After 1 hr, animals (3 mice/group) are killed by cervical fracture, and the ascites are treated with heparin, collected, pooled, and then centrifuged immediately in a Sorvall refrigerated centrifuge Model R2C-B at 800×g for 10 min (4°C). References [1]. Christman JK. 5-Azacytidine and 5-aza-2'-deoxycytidine as inhibitors of DNA methylation: mechanistic studies and their implications for cancer therapy. Oncogene. 2002 Aug 12;21(35):5483-95. [2]. Creusot F, et al. Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidineand 5-aza-2'-deoxycytidine. J Biol Chem. 1982 Feb 25;257(4):2041-8. [3]. Li LH,et al. Cytotoxicity and mode of action of 5-azacytidine on L1210 leukemia. Cancer Res. 1970 Nov;30(11):2760-9. Chemical & Physical Properties Density 2.1±0.1 g/cm3 Boiling Point 534.5±60.0 °C at 760 mmHg Melting Point 226-232 °C (dec.)(lit.) Molecular Formula C8H12N4O5 Molecular Weight 244.205 Flash Point 277.0±32.9 °C Exact Mass 244.080765 PSA 143.72000 LogP -1.99 Vapour Pressure 0.0±3.2 mmHg at 25°C Index of Refraction 1.823 InChIKey NMUSYJAQQFHJEW-KVTDHHQDSA-N SMILES Nc1ncn(C2OC(CO)C(O)C2O)c(=O)n1 Water Solubility 0.5-1.0 g/100 mL at 21 ºC |
| Use of | 5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. Properties Articles219 Name 5-azacytidine Synonym More Synonyms Azacitidine (5-Azacytidine) Biological Activity Description 5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. Related Catalog Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Epigenetics >> DNA Methyltransferase Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Cancer Nucleoside Antimetabolite/Analog References [1]. Christman JK. 5-Azacytidine and 5-aza-2'-deoxycytidine as inhibitors of DNA methylation: mechanistic studies and their implications for cancer therapy. Oncogene. 2002 Aug 12;21(35):5483-95. [2]. Creusot F, et al. Inhibition of DNA methyltransferase and induction of Friend erythroleukemia cell differentiation by 5-azacytidineand 5-aza-2'-deoxycytidine. J Biol Chem. 1982 Feb 25;257(4):2041-8. Chemical & Physical Properties Molecular Formula C8H12N4O5 Exact Mass 244.080765 PSA 143.72000 LogP -1.99 Index of Refraction 1.823 InChIKey NMUSYJAQQFHJEW-KVTDHHQDSA-N SMILES Nc1ncn(C2OC(CO)C(O)C2O)c(=O)n1 |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 20.0% |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 Names specified by the United Nations (UN) European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Dangerous Regulations: No International Maritime Transport Dangerous Regulations Maritime Pollutants: No International Air Transport Risk Regulations: No 14.6 Special reminder to users No data available See reverse side of invoice or packing slip. |
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