Azacitidine (5-Azacytidine) structure
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Common Name | Azacitidine (5-Azacytidine) | ||
|---|---|---|---|---|
| CAS Number | 320-67-2 | Molecular Weight | 244.205 | |
| Density | 2.1±0.1 g/cm3 | Boiling Point | 534.5±60.0 °C at 760 mmHg | |
| Molecular Formula | C8H12N4O5 | Melting Point | 226-232 °C (dec.)(lit.) | |
| MSDS | Chinese USA | Flash Point | 277.0±32.9 °C | |
| Symbol |
GHS07, GHS08 |
Signal Word | Danger | |
Use of Azacitidine (5-Azacytidine)5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. |
This table lists Chinese names, IUPAC names and various aliases of this chemical substance.
| Name | 5-azacytidine |
|---|---|
| Synonym | More Synonyms |
This table contains bioactivity, target information and biological‑assay experimental data of this compound.
| Description | 5-Azacytidine is a nucleoside analogue of cytidine that specifically inhibits DNA methylation by trapping DNA methyltransferases. |
|---|---|
| Related Catalog | |
| 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 |
This table shows physicochemical parameters including melting point, boiling point, density, solubility and optical rotation. Missing data is marked as N/A.
| 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 |
This table provides MSDS information including hazard classification, first‑aid, fire‑fighting, spill handling, operation and storage instructions.
This table summarizes toxicological test data, acute & chronic toxicity and ecological hazard parameters for this chemical.
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATAACUTE TOXICITY DATA
MUTATION DATA
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This table covers safety warnings, protective measures, incompatible substances and disposal guidelines for this compound.
| Symbol |
GHS07, GHS08 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H302-H350 |
| Precautionary Statements | P201-P308 + P313 |
| Personal Protective Equipment | Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges |
| Hazard Codes | T:Toxic |
| Risk Phrases | R45;R46;R22 |
| Safety Phrases | S53-S22-S36/37/39-S45 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | XZ3017500 |
| HS Code | 2934999090 |
This table presents publicly reported synthetic routes, reaction conditions, reactants and product information of the compound.
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Azacitidine (5-... CAS#:320-67-2 |
| Literature: ScinoPharm Taiwan Ltd. Patent: US2010/36112 A1, 2010 ; Location in patent: Page/Page column 7 ; |
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Azacitidine (5-... CAS#:320-67-2 |
| Literature: Ionescu, Dumitru; Blumbergs, Peter Patent: US2004/186283 A1, 2004 ; Location in patent: Page 8 ; |
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Azacitidine (5-... CAS#:320-67-2 |
| Literature: SICOR INC.; BIGATTI, Ettore; LUX, Giovanna; PAIOCCHI, Maurizio; GIOLITO, Andrea; TOSI, Simone Patent: WO2010/17374 A1, 2010 ; Location in patent: Page/Page column 18 ; |
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| Literature: EP2371825 A1, ; Page/Page column 9 ; |
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| Literature: EP2371825 A1, ; Page/Page column 9 ; |
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| Literature: US2014/135490 A1, ; Page/Page column ; |
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Azacitidine (5-... CAS#:320-67-2 |
| Literature: Vujjini, Satish Kumar; Varanasi, Ganesh; Arevelli, Srinivas; Kandala, Sreenatha Charyulu; Tirumalaraju, Satyanarayana Raju; Bandichhor, Rakeshwar; Kagga, Mukkanti; Cherukupally, Praveen Organic Process Research and Development, 2013 , vol. 17, # 2 p. 303 - 306 |
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| Literature: WO2009/16617 A2, ; Page/Page column 15-16 ; |
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| Literature: Journal of Pharmaceutical Sciences, , vol. 70, # 11 p. 1228 - 1232 |
This table lists upstream starting materials and downstream derivative products related to this chemical.
| Precursor 9 | |
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| DownStream 1 | |
This table shows customs‑related data including HS‑code, tariff and regulatory conditions for import and export.
| HS Code | 2934999090 |
|---|---|
| Summary | 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0% |
This table lists relevant public references with title, journal and publication metadata for this compound.
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The high mobility group A2 protein epigenetically silences the Cdh1 gene during epithelial-to-mesenchymal transition.
Nucleic Acids Res. 43(1) , 162-78, (2015) The loss of the tumour suppressor E-cadherin (Cdh1) is a key event during tumourigenesis and epithelial-mesenchymal transition (EMT). Transforming growth factor-β (TGFβ) triggers EMT by inducing the e... |
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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.
Chem. Res. Toxicol. 23 , 171-83, (2010) Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental... |
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Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).
J. Sci. Ind. Res. 65(10) , 808, (2006) Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ... |
This table collects all English aliases, systematic names and CAS‑related synonyms of the compound.
| Vidaza |
| 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxyméthyl)tétrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one |
| EINECS 206-280-2 |
| [14C]-Azacitidine |
| 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 |
| 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,3,5-triazin-2(1H)-one |
| 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 |
| 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-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 |
This section contains frequently‑asked‑questions about this compound, including basic parameters, properties, storage conditions and corresponding answers.
| Q: How is the water solubility of 5-azacytidine? |
| A: Water solubility of 5-azacytidine: 0.5-1.0 g/100 mL at 21 ºC. |
| Q: What are the upstream materials of 5-azacytidine? |
| A: Related upstream materials(CAS) of 5-azacytidine: 6974-32-9;52523-35-0;13035-61-5;10302-78-0;931-86-2;14215-97-5;28708-32-9;56787-28-1;65126-88-7. |
| Q: What is the CAS number of 5-azacytidine? |
| A: CAS number of 5-azacytidine is 320-67-2. |
| Q: What is the InChIKey of 5-azacytidine? |
| A: InChIKey of 5-azacytidine is NMUSYJAQQFHJEW-KVTDHHQDSA-N. |
| Q: What is the boiling point of 5-azacytidine? |
| A: Boiling point of 5-azacytidine is 534.5±60.0 °C at 760 mmHg. |
| Q: What are the downstream products of 5-azacytidine? |
| A: Related downstream products(CAS) of 5-azacytidine: 65370-90-3. |
| Q: What is the SMILES notation of 5-azacytidine? |
| A: SMILES notation of 5-azacytidine is Nc1ncn(C2OC(CO)C(O)C2O)c(=O)n1. |
| Q: What is the molecular weight of 5-azacytidine? |
| A: Molecular weight of 5-azacytidine is 244.205. |
| Q: What is the polar surface area (PSA) of 5-azacytidine? |
| A: Polar surface area (PSA) of 5-azacytidine is 143.72000. |
| Q: What is the safety information for 5-azacytidine? |
| A: Safety information for 5-azacytidine: S53-S22-S36/37/39-S45. |
This table lists manufacturers and suppliers of this compound, including vendor names and product supply reference information.
| Shanghai Nianxing Industrial Co., Ltd |
| Dayang Chem (Hangzhou) Co., Ltd. |
| Henan Tianfu Chemical Co., Ltd. |