CAS No.320-67-2,5-Azacytidine Suppliers

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Basic Information

Molecular Structure:
CAS No.:	320-67-2
Name:	5-Azacytidine
Article Data:	38

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

Synthetic route

: 5-azacytidine mono-hydrochloride

: 320-67-2
5-azacytidine

Conditions

Conditions	Yield
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

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

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

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

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

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

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

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;

: C17H26N4O8Si

: 320-67-2
5-azacytidine

Conditions

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

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;

Raw Materials

931-86-2

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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 NO_x.

Hazard Codes: Toxic 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.