Name | 5-Aza-2'-deoxycytidine |
Synonyms | Decitabine 5-azadeoxycytidine Decitabine(NSC127716) 5-Aza-2'-deoxycytidine 2'-desoxy-5-azacytidine Decitabine intermediates 4-amino-1-(2-deoxypentofuranosyl)-1,3,5-triazin-2(1H)-one 4-Amino-1-(2-deoxy-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one 4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,3,5-triazin 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 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one 5-triazin-2(1h)-one,4-amino-1-(2-deoxy-beta-d-erythro-pentofuranosyl)-3 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one |
CAS | 2353-33-5 |
EINECS | 219-089-4 |
InChI | InChI=1/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 |
InChIKey | XAUDJQYHKZQPEU-KVQBGUIXSA-N |
Molecular Formula | C8H12N4O4 |
Molar Mass | 228.21 |
Density | 1.3771 (rough estimate) |
Melting Point | ~200°C (dec.) |
Boling Point | 370.01°C (rough estimate) |
Specific Rotation(α) | D22 +68.5° (30 min) +57.8° (6 hr) (c = 0.5 in water) |
Flash Point | 247.6°C |
Solubility | acetic acid/water (1:1): 50mg/mL |
Vapor Presure | 1.78E-11mmHg at 25°C |
Appearance | White crystalline powder |
Color | White to Off-white |
Merck | 14,2853 |
BRN | 617982 |
pKa | 14.02±0.60(Predicted) |
Storage Condition | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
Stability | Stable. May be light or air sensitive. Incompatible with strong oxidizing agents. |
Sensitive | Easily absorbing moisture |
Refractive Index | 1.6590 (estimate) |
MDL | MFCD00043011 |
In vitro study | Decitabine effectively inhibited DNA synthesis in a dose-dependent manner, with IC50 values of 100 ng/mL and 1 ng/mL for HL-60 and KG1a leukemia cells, respectively. Decitabine inhibited cell growth in a dose-and time-dependent manner, with IC50 of about 100 ng/mL and 10 ng/mL for 72 and 96 hours of treatment of HL-60 and KG1a leukemia cells, respectively. The latest research shows that Decitabine acts on anaplastic large cell lymphoma (ALCL), has anti-proliferative and pro-apoptotic activities, and inhibits KARPAS-299 cells [ |
In vivo study | Decitabine at 2.5 mg/kg dose for ALK |
Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R68 - Possible risk of irreversible effects R61 - May cause harm to the unborn child |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S36/37 - Wear suitable protective clothing and gloves. |
WGK Germany | 3 |
RTECS | XZ3012000 |
FLUKA BRAND F CODES | 10-34 |
HS Code | 29349990 |
Toxicity | LD50 in mice (mg/kg): 190 i.p. (Momparler, 1985) |
Reference Show more | 1. Hu Baocui Hao Jinqi Hou Ruili et al. Effects of 5-aza-2-deoxycytidine on CYP2E1 Gene Methylation and Protein Expression in ADIH Model Rats [J]. Journal of Baotou Medical College, 20202036 Volume 1, 36-39 Page 42 2020: national natural science foundation. 2. [IF = 4.24] Ling Guo et al."Purple sweet anthocyanins elicit calcium overload-induced cell death by inhibiting the calcium-binding protein S100A4 in acute lymphoblastic leukemia." Food Biosci. 2021 Aug;42:101214 |
EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
Treatment of myelodysplastic syndrome | 5-aza-2'-deoxycytosine nucleoside, also known as decitabine, 5-aza-2'-deoxycytidine acid, is a natural adenosine analog of 2 '-deoxycytidine acid, which reduces DNA methylation by inhibiting DNA methyltransferase, so as to inhibit the proliferation of tumor cells and prevent the occurrence of drug resistance, it is the strongest known DNA methylation specific inhibitor. It belongs to the S-phase cell cycle specific drugs and is suitable for the treatment of myelodysplastic syndrome (MDS). Demethylated drugs can activate tumor cell tumor suppressor genes and enhance the expression of differentiation genes and other regulatory genes, so they can achieve the purpose of treating MDS. 5-aza-2'-deoxycytosine nucleoside (decitabine) is phosphorylated and exerts its anti-tumor effect. It acts directly on DNA and inhibits DNA methyltransferase, thus causing DNA hypomethylation and cell differentiation and death. Decitabine inhibits DNA methylation in vitro, but does not affect DNA synthesis. It can cause demethylation of tumor cells and restore the normal function of genes, which is very important for controlling cell differentiation and proliferation. But non-proliferative cells are not sensitive to decitabine. In 2006, the U.S. Food and Drug Administration approved decitabine for the treatment of MDS. |
Mechanism of action | Decitabine is a pyrimidine analog (5-aza-2'-deoxycytosine nucleoside), which is the 2-deoxy-D-ribose form of 5-azacytosine nucleoside. Decitabine is converted into triphosphate by intracellular action, and triphosphate is incorporated into the DNA strand to inhibit DNA methylation, thereby increasing the expression of dormant genes (including tumor suppressor genes). In vivo and in vitro studies have shown that decitabine can induce bone marrow cell differentiation, thus normalizing bone marrow development in patients with partial bone marrow dysplasia. |
adverse reactions | (1) neutropenia (symptom), thrombocytopenia (symptom), anemia, vomiting, fatigue, fever, cough, nausea, constipation, diarrhea, hyperglycemia, febrile neutropenia (symptom). (2) Large doses can cause neurotoxicity, manifested as drowsiness, aphasia, hemiplegia, etc., but can return to normal after stopping the drug. |
Biological activity | Decitabine (Deoxycytidine, Dacogen, 5-aza-2-deoxycytidine, 5-AZA-dC, 5-aza-CdR, NSC 127716) is a DNA methyltransferase inhibitor that integrates into DNA, causes DNA hypomethylation, and causes DNA replication to stagnate intra-S-phase. Decitabine is used to treat myelodysplastic syndrome (MDS). Decitabine can induce cell cycle arrest and apoptosis in a variety of cancer cell lines. |
Target | Value |
Use | is an epigenetic modifier that can inhibit DNA transmethylase activity and lead to DNA demethylation (hypomethylation) And activate genes by remodeling "open" chromatin; when demethylation is combined with histone acetylation, genes can be activated synergistically; 5 ′-Nitrogen deoxycytosine causes DNA demethylation or semi-demethylation; DNA demethylation can regulate gene expression, and the detectable structure through "open" chromatin improves nuclease sensitivity. This remodeling chromatin structure allows transcription factors to connect gene promoter regions, transcription complex assembly and gene expression Decitabine has anti-tumor activity and is manifested as a dual mechanism of dose difference. It has cytotoxic effect at high concentration and demethylation at low concentration. Acting on proliferative (S-phase) cells. |
category | toxic substances |
toxicity classification | highly toxic |
acute toxicity | vein-mouse LD50: 22 mg/kg; Abdominal cavity-mouse LD50: 190 mg/kg |
flammability hazard characteristics | combustible; combustion produces toxic nitrogen oxide smoke |
storage and transportation characteristics | ventilation and low temperature drying; separate from warehouse food raw materials |
fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |