CAS Number2353-33-5
Synonyms4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; MFCD00043011; 5-AZA-CDR; DAC; 5-AZA-DC; Decitabine; 5-DEOXY-2'-AZACYTIDINE; EINECS 219-089-4; 4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one; 5-Aza-1-(2-deoxy-β-D-ribofuranosyl)cytosine; 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one; 2'-deoxy-5-azacytidine; 5-Aza-2'-deoxycytidine; Dacogen; 2-Desoxy-5-azacytidine; 5-azadeoxycytidine; 5-Aza-2′-deoxycytidine; 5-Aza-2'-deoxycytidine; 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-on; 4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,3,5-triazin-2(1H)-one; 4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-s-triazin-2(1H)-one
Molecular FormulaC8H12N4O4
Molecular Weight228.21
Purity≥97%
Density1.9±0.1 g/cm3
Boiling Point485.8±55.0 °C at 760 mmHg
Melting Point~200 °C (dec.)
Appearancepowder
EINECS219-089-4
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 2353-33-5 |
| Catalog No. | 2A-9010022 |
| Chinese Name | 地西他滨 |
| Synonyms | 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one; MFCD00043011; 5-AZA-CDR; DAC; 5-AZA-DC; Decitabine; 5-DEOXY-2'-AZACYTIDINE; EINECS 219-089-4; 4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one; 5-Aza-1-(2-deoxy-β-D-ribofuranosyl)cytosine; 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one; 2'-deoxy-5-azacytidine; 5-Aza-2'-deoxycytidine; Dacogen; 2-Desoxy-5-azacytidine; 5-azadeoxycytidine; 5-Aza-2′-deoxycytidine; 5-Aza-2'-deoxycytidine; 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-on; 4-Amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-1,3,5-triazin-2(1H)-one; 4-Amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-s-triazin-2(1H)-one |
| Molecular Formula | C8H12N4O4 |
| Molecular Weight | 228.21 |
| Purity | ≥97 |
| Density | 1.9±0.1 g/cm3 |
| Boiling Point | 485.8±55.0 °C at 760 mmHg |
| Melting Point | ~200 °C (dec.) |
| Appearance | powder |
| Water Solubility | acetic acid/water (1:1): 50 mg/mL |
| Storage Condition | Store at -20°. |
| Application | Decitabine (NSC 127716) is a DNA methyltransferase inhibitor commonly used to treat myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML). |
| EINECS | 219-089-4 |
| PubChem ID | 24890797 |
| MDL Number | MFCD00043011 |
| SMILES | NC1=NC(=O)N(C=N1)[C@H]2C[C@H](O)[C@@H](CO)O2 |
| InChI | 1S/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1 |
| InChI Key | XAUDJQYHKZQPEU-KVQBGUIXSA-N |
| Beilstein/REAXYS | 617982 |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| MSDS | msds/10022_1_2353_33_5.pdf |
| Bioactivity | Decitabine (NSC 127716) is a DNA methyltransferase inhibitor commonly used to treat myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML). Related Catalog Signaling Pathways >> Epigenetics >> DNA Methyltransferase Research Areas >> Cancer Target DNMT1 DNMT3A DNMT3B In Vitro Decitabine treatment significantly inhibits cell growth of SNU719, NCC24 and KATOIII 96 hours after exposure to decitabine. Decitabine induces G2/M arrest and apoptosis in EBVaGC, inhibits invasion ability, and up-regulates E-cadherin expression for EBVaGC[1]. Tri-acetylation on the H4 N-terminal tail (H4K8acK12acK16ac) is reduced after DAC treatment in MDS-L sensitive cells[2]. Decitabine up-regulates DCTPP1 and dUTPase expression in HeLa cells[3]. In Vivo Decitabine (1.0 mg/kg, p.o.) in combination with tetrahydrouridine (THU) causes severe toxicity occurs in females, and results in an increased sensitivity to decitabine toxicity correlating with decitabine plasma levels[4]. Kinase Assay The pyrophosphohydrolase activity of DCTPP1 is determined using a continuous spectrophotometric assay. In a standard reaction (1 mL final volum), 10-250 μM of the nucleotide substrate is incubated in reaction buffer (20 mM MgCl2, 100 mM KCl, 0.75 mg/mL BSA and 4 mM DTT) with concentrations ranging from 0.1-1 μM of DCTTP1. All reactions are carried out at 25°C. Cell Assay Cell viability is analyzed by cell count and MTS assay. SNU719, NCC24 and KATOIII are seeded at a density of 5×104 cells/mL and cultured with only RPMI-1640 supplemented with FBS for 24 hours. After 24 hours of incubation, cells are treated in the presence or absence of Decitabine (DAC) for 120 hours. Cells for cell counts are trypsinized and counted at 0, 24, 48, 72, 96 and 120 hours after DAC treatment. Viable cells are determined by trypan blue exclusion. For MTS assay, cells (SNU719 and NCC24: 1x104/well, KATOIII: 1x103/well) are eeded onto 96-well dishes. After seeding, MTS is added into the well at the indicated period. After incubation for 1 hour, the absorbance is measured at 490 nm. Animal Admin Mice are assigned to four dose groups and a vehicle control group. Animals are gavaged with Decitabine (DAC) or its vehicle 1 hour ± 5 minutes after administration of tetrahydrouridine (THU) or its vehicle at a dose volume of 10 mL/kg. The DAC doses are selected based on the range finding study in which the mice tolerated six oral doses (2x/week) of 0.1, 0.2 and 0.4 mg/kg DAC in combination with a fixed dose of 167 mg/kg THU. A fixed THU dose (500 mg/m2) and the optimal timing between THU and DAC administration (60 min) are selected. Conversion of milligrams per body surface area dose in mice into milligrams per kilogram body weight dose estimation is based on Michaelis constant (Km) values for mice. In brief, the mouse dose in milligrams per body surface area (500 mg/m2) is divided by the Km of 3 to convert the dose to milligrams per kilogram body weight (167 mg/kg). The working body weight range of mice in the guideline is 11-34 gram; the body weight range of mice used in this study is 24-38 gram. References [1]. Nakamura M, et al. Decitabine inhibits tumor cell proliferation and up-regulates E-cadherin expression in Epstein-Barr virus-associated gastric cancer. J Med Virol. 2016 Jul 19. [2]. Zhang C, et al. Quantitative proteomic analysis of histone modifications in decitabine sensitive and resistant leukemia cell lines. Clin Proteomics. 2016 Jul 5;13:14. [3]. Requena CE, et al. The nucleotidohydrolases DCTPP1 and dUTPase are involved in the cellular response to decitabine. Biochem J. 2016 Jun 20. [4]. Terse P, et al. Subchronic oral toxicity study of decitabine in combination with tetrahydrouridine in CD-1 mice. Int J Toxicol. 2014 Mar-Apr;33(2):75-85. [5]. Yu J, et al. DNA methyltransferase expression in triple-negative breast cancer predicts sensitivity to decitabine. J Clin Invest. 2018 Jun 1;128(6):2376-2388. Chemical & Physical Properties Density 1.9±0.1 g/cm3 Boiling Point 485.8±55.0 °C at 760 mmHg Melting Point ~200 °C (dec.) Molecular Formula C8H12N4O4 Molecular Weight 228.205 Flash Point 247.6±31.5 °C Exact Mass 228.085861 PSA 123.49000 LogP -1.93 Vapour Pressure 0.0±2.8 mmHg at 25°C Index of Refraction 1.780 InChIKey XAUDJQYHKZQPEU-KVQBGUIXSA-N SMILES Nc1ncn(C2CC(O)C(CO)O2)c(=O)n1 Stability Stable. May be light or air sensitive. Incompatible with strong oxidizing agents. Water Solubility acetic acid/water (1:1): 50 mg/mL |
| Use of | Decitabine (NSC 127716) is a DNA methyltransferase inhibitor commonly used to treat myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML). Properties Articles192 Name 5-aza-2'-deoxycytidine Synonym More Synonyms Decitabine Biological Activity Description Decitabine (NSC 127716) is a DNA methyltransferase inhibitor commonly used to treat myelodysplastic syndromes (MDS) and acute myeloid leukemia (AML). Related Catalog Signaling Pathways >> Epigenetics >> DNA Methyltransferase Research Areas >> Cancer References [1]. Nakamura M, et al. Decitabine inhibits tumor cell proliferation and up-regulates E-cadherin expression in Epstein-Barr virus-associated gastric cancer. J Med Virol. 2016 Jul 19. [2]. Zhang C, et al. Quantitative proteomic analysis of histone modifications in decitabine sensitive and resistant leukemia cell lines. Clin Proteomics. 2016 Jul 5;13:14. [3]. Requena CE, et al. The nucleotidohydrolases DCTPP1 and dUTPase are involved in the cellular response to decitabine. Biochem J. 2016 Jun 20. [5]. Yu J, et al. DNA methyltransferase expression in triple-negative breast cancer predicts sensitivity to decitabine. J Clin Invest. 2018 Jun 1;128(6):2376-2388. Chemical & Physical Properties Molecular Formula C8H12N4O4 Exact Mass 228.085861 PSA 123.49000 LogP -1.93 Index of Refraction 1.780 InChIKey XAUDJQYHKZQPEU-KVQBGUIXSA-N Stability Stable. May be light or air sensitive. Incompatible with strong oxidizing agents. |
| Transport Info | Product name: Purity: 98.0% |
| MSDS Transport Info | Module 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified |
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