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320-67-2

Basic Information
CAS No.: 320-67-2
Name: 5-Azacytidine
Molecular Structure:
Molecular Structure of 320-67-2 (5-Azacytidine)
Formula: C8H12N4O5
Molecular Weight: 244.21
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: ToxicT
Risk Codes: 45-46-22
Safety: 53-22-36/37/39-45
Transport Information:
PSA: 143.72000
LogP: -2.58680
Synthetic route

5-azacytidine mono-hydrochloride

320-67-2

5-azacytidine

Conditions
ConditionsYield
With triethylamine In methanol at 25 - 30℃; for 2h; Product distribution / selectivity; Inert atmosphere;99.13%

p-chlorobenzoyl azacitidine

320-67-2

5-azacytidine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;

C17H26N4O8Si

320-67-2

5-azacytidine

Conditions
ConditionsYield
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
ConditionsYield
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;
931-86-2

5-azacytosine

14215-97-5

1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose

320-67-2

5-azacytidine

Conditions
ConditionsYield
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux;
Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose; trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2.16667h; Reflux;
Stage #3: With methanol; sodium methylate at 50℃; for 1h;
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux;
Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose In dichloromethane for 2h; Reflux;
Stage #3: With methanol; sodium methylate at 50℃; for 1h; Product distribution / selectivity;
931-86-2

5-azacytosine

28708-32-9

1,2,3,5-tetra-O-acetyl-D-ribofuranose

320-67-2

5-azacytidine

Conditions
ConditionsYield
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux;
Stage #2: 1,2,3,5-tetra-O-acetyl-D-ribofuranose; trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2.16667h; Reflux;
Stage #3: With methanol; sodium methylate at 50℃; for 1h; Product distribution / selectivity;
Stage #1: 5-azacytosine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 1.5h; Reflux;
Stage #2: 1,2,3,5-tetra-O-acetyl-D-ribofuranose With trimethylsilyl trifluoromethanesulfonate In dichloromethane for 2h; Reflux;
Stage #3: With methanol; sodium methylate at 50℃; for 1h; Product distribution / selectivity;

C17H23N3O6

320-67-2

5-azacytidine

Conditions
ConditionsYield
With methanol; sodium methylate at 20℃; for 12h;10.3 g

C32H34N4O7Si

320-67-2

5-azacytidine

Conditions
ConditionsYield
With methanol; sodium methylate In dichloromethane at 20℃; for 12h;8 g
110-16-7

maleic acid

320-67-2

5-azacytidine

5-azacytidine maleic acid

Conditions
ConditionsYield
In methanol; water for 0.333333h;99%
98-92-0

nicotinamide

320-67-2

5-azacytidine

5-azacytidine nicotinamide

Conditions
ConditionsYield
In methanol; water for 0.333333h;99%
320-67-2

5-azacytidine

5-azacytidine zinc chloride

Conditions
ConditionsYield
With zinc(II) chloride In methanol; water for 0.333333h;98%
320-67-2

5-azacytidine

62488-57-7

4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5,6-dihydro-1,3,5-triazin-2(1H)-one

Conditions
ConditionsYield
With sodium tetrahydroborate In water at 20℃; for 1.5h;97%
320-67-2

5-azacytidine

5-azacytidine mono-hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol; isopropyl alcohol at 25 - 30℃; for 4h; Product distribution / selectivity; Inert atmosphere;93.29%
104-15-4

toluene-4-sulfonic acid

320-67-2

5-azacytidine

65370-90-3

2’, 3’-O-isopropyl-5-N-cytidine

Conditions
ConditionsYield
In acetone for 24h; Inert atmosphere;90%
320-67-2

5-azacytidine

5-azacytidine hemisulfate

Conditions
ConditionsYield
With sulfuric acid In methanol at 25 - 30℃; for 2.5h; Product distribution / selectivity; Inert atmosphere;87.7%
320-67-2

5-azacytidine

1401238-97-8

5-azacytidine mono-hydrobromide

Conditions
ConditionsYield
With hydrogen bromide In methanol; acetic acid at 25 - 30℃; for 12.5h; Product distribution / selectivity; Inert atmosphere;67%
18162-48-6

tert-butyldimethylsilyl chloride

320-67-2

5-azacytidine

C26H54N4O5Si3

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 15h; Cooling with ice;67%
75-77-4

chloro-trimethyl-silane

320-67-2

5-azacytidine

2',3',5'-tri(trimethylsilyl)-5-azacytidine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice;64%
In pyridine Yield given;
40615-36-9

4,4'-dimethoxytrityl chloride

320-67-2

5-azacytidine

107036-45-3

5'-O-(4,4'-dimethoxytrityl)-5-azacytidine

Conditions
ConditionsYield
With pyridine59%
In pyridine2.89 g (59%)
75-75-2

methanesulfonic acid

320-67-2

5-azacytidine

879492-75-8

5-azacytidine mesylate

Conditions
ConditionsYield
In methanol at 25 - 30℃; for 2h; Product distribution / selectivity; Inert atmosphere;52.7%
320-67-2

5-azacytidine

58479-61-1

tert-butylchlorodiphenylsilane

C24H30N4O5Si

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 15 - 30℃; for 2h; Cooling with ice;48%
320-67-2

5-azacytidine

1137569-06-2

5-azacytidine 5'-elaidic acid ester

Conditions
ConditionsYield
Stage #1: 5-azacytidine With hydrogenchloride In diethyl ether; ISOPROPYLAMIDE at 20℃;
Stage #2: elaidoyl chloride In ISOPROPYLAMIDE at 20 - 30℃;
Stage #3: With water; sodium hydrogencarbonate In ethyl acetate
43%
770-09-2

benzyltrimethylsilane

320-67-2

5-azacytidine

5’-O-(t-butyldimethylsilyl)-5-azacytidine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 17h; Cooling with ice;23%
320-67-2

5-azacytidine

2-(1-bromo-1-methylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2-(1-bromo-1-methylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

C17H29BN4O7

Conditions
ConditionsYield
Stage #1: 5-azacytidine With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;
Stage #2: 2-(1-bromo-1-methylethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; regioselective reaction;
18%
320-67-2

5-azacytidine

2524-64-3

chlorophosphoric acid diphenyl ester

C20H21N4O8P

Conditions
ConditionsYield
With pyridine at 0℃; for 0.1h;16%
75-77-4

chloro-trimethyl-silane

320-67-2

5-azacytidine

5'-O-trimethylsilyl-5-azacytidine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 15 - 30℃; for 1h; Cooling with ice;14%
320-67-2

5-azacytidine

100-51-6

benzyl alcohol

C22H25N4O8P

Conditions
ConditionsYield
Stage #1: 5-azacytidine With triethyl phosphate; trichlorophosphate at 0℃; for 0.1h;
Stage #2: benzyl alcohol With pyridine at 0℃; for 1h;
13%
18162-48-6

tert-butyldimethylsilyl chloride

320-67-2

5-azacytidine

5'-O-(t-butyldimethylsilyl)-5-azacytidine

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 3h; Cooling with ice;12%
320-67-2

5-azacytidine

2508-81-8

4,5-dihydro-1,2-dideoxy-α-D-ribofuranoso[1,2-d]-1,3-oxazol-2-one

Conditions
ConditionsYield
In water Heating;
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    5-Azacytidine Basic information Description Indication Contraindications Dosage Mechanism of Action Elimination Adverse reactions Precautions Product Name: 5-Azacytidine Synonyms: Antibiotic U 18496-15N4;Azacitidine-15N4;Azacytidine-15N4;

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    5-Azacytidine 320-67-2

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    5-Azacytidine Quick details Chemical Name: 5-Azacytidine CAS No.: 320-67-2 Molecular Formula: C8H12Na4O5 Molecular weight: 244.2 Appearance: White powder 5-Azacytidine COA Item Specific

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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: ToxicT
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.