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| CAS No.: | 320-67-2 |
|---|---|
| Name: | 5-Azacytidine |
| Molecular Structure: | |
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|
|
| Formula: | C8H12N4O5 |
| Molecular Weight: | 244.207 |
| Synonyms: | Azacitidine;U 18496;4-Amino-1-beta-D-ribofuranosyl-1,3,5-traizin-2(1H)-one;Azacitidine [USAN:INN];s-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl- (8CI);4-amino-1-[(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one;1,3,5-Triazin-2 (1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-;5-AZAC;2-(beta-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-one;s-Triazin-2 (1H)-one, 4-amino-1-.beta.-D-ribofuranosyl-;Anitibiotic U 18496;Vidaza;4-amino-1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one;4-amino-1-[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one;Mylosar;Azacytidine, 5-;1,3,5-Triazin-2(1H)-one, 4-amino-1-beta-D-ribofuranosyl-;4-Amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one;Azacitidina [INN-Spanish];Prestwick_972;Ladakamycin;5-AZCR;Antibiotic U 18496;Azacitidinum [INN-Latin];4-Amino-1-beta-D-ribofuranosyl-1,3,5-triazine-2(1H)-one;5-AC;5 AZC;4-amino-1-beta-D-ribofuranosyl-1,3,5-triazin-2(1H)-one;1,3,5-Triazin-2(1H)-one,4-amino-1-a-Dribofuranosyl-; |
| EINECS: | 206-280-2 |
| Density: | 2.08 g/cm3 |
| Melting Point: | 226-232 °C (dec.)(lit.) |
| Boiling Point: | 534.5 °C at 760 mmHg |
| Flash Point: | 277 °C |
| Solubility: | 0.5-1.0 g/100 mL at 21 °C in water |
| Appearance: | White-to-off-white crystalline solid |
| Hazard Symbols: |
 T
|
| Risk Codes: | 45-46-22 |
| Safety: | 53-22-36/37/39-45 |
| PSA: | 143.72000 |
| LogP: | -2.58680 |
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- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| With triethylamine In methanol at 25 - 30℃; for 2h; Product distribution / selectivity; Inert atmosphere; | 99.13% |
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| With ammonia In methanol for 2h; | 89.2% |
| With sodium methylate In methanol for 2h; Inert atmosphere; | 74.4% |
- 10302-78-0
2,3,5-tri-O-acetyl-β-D-ribofuranose-4-amino-1,3,5-triazine
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| With sodium methylate In methanol for 2h; Inert atmosphere; | 80.2% |
| With methanol; sodium methylate at 20 - 25℃; for 1.58333h; Product distribution / selectivity; | 75% |
| With sodium methylate In methanol for 3h; Solvent; | 38.8% |
- 28998-36-9
4-amino-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| With sodium methylate In methanol for 2h; Inert atmosphere; | 75.9% |
| With ammonia In methanol at 0 - 20℃; for 7h; | 60% |
- 56787-28-1
2',3',5'-tri-O-acetylcytidine
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| With N-butylamine In methanol at 65℃; for 1h; | 75.3% |
- 6974-32-9
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
- 52523-35-0
2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| Stage #1: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose; 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; trifluorormethanesulfonic acid In acetonitrile at 55℃; for 12.5h; Industry scale; Stage #2: With methanol; sodium methylate In dimethyl sulfoxide; acetonitrile at 22 - 23℃; for 3.75h; | 71% |
- 13035-61-5
1,2,3,5-tetraacetylribose
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| Stage #1: 5-azacytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 20h; Heating / reflux; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 20h; Stage #3: With sodium methylate; sodium hydrogencarbonate more than 3 stages; | 41.3% |
| Stage #1: 5-azacytosine With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 20h; Heating / reflux; Stage #2: 1,2,3,5-tetraacetylribose With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 20h; Stage #3: With sodium methylate; sodium hydrogencarbonate more than 3 stages; |
- 65126-88-7
N-(Formylamidino)-N'-β-D-ribofuranosylharnstoff
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| at 37℃; Rate constant; pH 9.5; other temperature, pH; decomposition of 5-aza-2'-deoxycytidine and 5-azacytidine on alkali and neutral solutions, HPLC study; |
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| With sodium methylate In methanol |
- 52523-35-0
2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine
- 13035-61-5
1,2,3,5-tetraacetylribose
- 320-67-2
5-azacytidine
| Conditions | Yield |
|---|---|
| Stage #1: 2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; 1,2,3,5-tetraacetylribose With tin(IV) chloride In 1,2-dichloro-ethane at 5 - 20℃; for 2.25h; Stage #2: With water; sodium hydrogencarbonate In 1,2-dichloro-ethane at 15 - 20℃; for 0.5h; Product distribution / selectivity; |
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Specification
1. Introduction of 5-Azacytidine
5-Azacytidine is one kind of white-to-off-white crystalline solid. Its IUPAC Name is 4-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one. Its Classification Code is Antimetabolites; Antimetabolites, antineoplastic; Antineoplastic; Antineoplastic Agents; Drug / Therapeutic Agent; Enzyme inhibitors; Human Data; Mutation data; Noxae; Reproductive Effect; Skin / Eye Irritant; Tumor data. It belongs to API intermediates;Antitumors for Research and Experimental Use;Biochemistry;Chemical Reagents for Pharmacology Research;Nucleosides and their analogs;Nucleosides, Nucleotides & Related Reagents;Bases & Related Reagents;Nucleotides;Carbohydrates & Derivatives.
5-Azacytidine is sensitive to oxidation. 5-Azacytidine is unstable in solution. 5-Azacytidine undergoes hydrolysis in aqueous buffers. 5-Azacytidine is incompatible with strong oxidizers.
It is Slightly water soluble. Unstable in solution.
2. Properties of 5-Azacytidine
Physical properties about 5-Azacytidine are:
(1)Index of Refraction: 1.823; (2)Molar Refractivity: 51.08 cm3; (3)Molar Volume: 117 cm3; (4)Surface Tension: 106.7 dyne/cm; (5)Density: 2.08 g/cm3; (6)Flash Point: 277 °C; (7)Enthalpy of Vaporization: 93.24 kJ/mol; (8)Boiling Point: 534.5 °C at 760 mmHg; (9)Melting Point: 226-232 °C (dec.)(lit.); (10)alpha: 40 °(C=1, H2O 22 °C); (11)storage temperature: 2-8 °C; (12)Water Solubility: 0.5-1.0 g/100 mL at 21 °C; (13)Vapour Pressure of Azacitidine: 1.18E-13 mmHg at 25 °C.
3. Structure Descriptors of 5-Azacytidine
(1)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;
(2)InChIKey=NMUSYJAQQFHJEW-KVTDHHQDSA-N; (3)Smiles:n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)nc1)=O
(3)Smiles: n1([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)c(nc(N)nc1)=O
4. Toxicity of 5-Azacytidine
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| bird - wild | LD50 | oral | 100mg/kg (100mg/kg) | Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. | |
| dog | LD50 | intravenous | 7200ug/kg (7.2mg/kg) | BLOOD: OTHER CHANGES | Advances in Pharmacology and Chemotherapy. Vol. 14, Pg. 285, 1977. |
| mouse | LD50 | intraperitoneal | 68mg/kg (68mg/kg) | Experientia. Vol. 22, Pg. 53, 1966. | |
| mouse | LD50 | intravenous | 229mg/kg (229mg/kg) | BEHAVIORAL: ATAXIA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | National Technical Information Service. Vol. PB84-211432, |
| mouse | LD50 | oral | 572mg/kg (572mg/kg) | Toxicology and Applied Pharmacology. Vol. 19, Pg. 382, 1971. | |
| quail | LD50 | oral | > 100mg/kg (100mg/kg) | Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982. | |
| women | TDLo | intravenous | 500ug/kg (.5mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 413, 1972. |
| women | TDLo | intravenous | 6mg/kg/10D-I (6mg/kg) | BLOOD: LEUKOPENIA BLOOD: AGRANULOCYTOSIS | Cancer Chemotherapy Reports, Part 1. Vol. 56, Pg. 413, 1972. |
5. Physical Properties of 5-Azacytidine
| Physical Property | Value | Units | Temp (deg C) | Source |
|---|---|---|---|---|
| Melting Point | 229 | deg C | EXP | |
| log P (octanol-water) | -3.830 | (none) | EST | |
| Water Solubility | 8.90E+04 | mg/L | 25 | EST |
| Vapor Pressure | 4.10E-12 | mm Hg | 25 | EST |
| Henry's Law Constant | 3.80E-21 | atm-m3/mole | 25 | EST |
| Atmospheric OH Rate Constant | 9.72E-11 | cm3/molecule-sec | 25 | EST |
6. Safety Information of 5-Azacytidine
Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic data. Poison by ingestion, intravenous, and intraperitoneal routes. Human systemic effects by intravenous route: nausea, vomiting and diarrhea, reduction in white cell count (luekopenia and agranulocytosis). An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
T
Risk Statements: 45-46-22
R45:May cause cancer.
R46:May cause heritable genetic damage.
R22:Harmful if swallowed.
Safety Statements: 53-22-36/37/39-45
S53:Avoid exposure - obtain special instructions before use.
S22:Do not breathe dust.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS of Azacitidine (CAS NO.320-67-2): XZ3017500
7. Uses of 5-Azacytidine
Azacitidine is mainly used in the treatment of myelodysplastic syndrome (MDS). It can also be used in vitro to remove methyl groups from DNA. 5-Azacytidine is a potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase. 5-azacytidine has been in the public eye for quite a while now, and it's been widely known as a powerful demethylating agent in clinical trials.