Azacytidine
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Azacytidine
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CAS No:
320-67-2
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Formula:
C8H12N4O5
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Chemical Name:
Azacytidine
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Synonyms:
1,3,5-Triazin-2(1H)-one,4-amino-1-β-D-ribofuranosyl-;s-Triazin-2(1H)-one,4-amino-1-β-D-ribofuranosyl-;4-Amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one;Antibiotic U 18496;5-Azacytidine;U 18496;NSC 102816;Azacitidine;Azacytidine;NSC 103-627;5-AZCR;Mylosar;5-AC;WR 183027;5-AzaC;5-AZC;Ladakamycin;Ledakamycin;Vidaza;CC 486;5-Azacitidine;52934-49-3;292869-98-8
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CAS No:
Characteristics
141
-2.2
White to Off-white lyophilized powder
1.4287 (rough estimate)
228-230 °C (decomp)
534.5°C at 760 mmHg
277ºC
1.823
H2O: 0.5-1.0 g/100 mL at 21 ºC
2-8°C
Oral-mouse LD50: 572 mg/kg; peritoneal-mouse LD50: 68 mg/kg
Flammable; burning produces toxic nitrogen oxide fumes; patient side effects: nausea, vomiting, diarrhea, leukopenia
40 º (C=1, H2O 22 ºC)
Safety Information
3
45-46-22
53-22-36/37/39-45
XZ3017500
T
Ventilated, low temperature and dry; stored separately from food materials in warehouse
Bulk: Samples of 5- azacitidine and 5- azacitidine hydrate were found to be stable at 25 °C and 60 °C for at least 30 days. Solution: Dilute aqueous solutions of 5-azacitidine have been found to be unstable at 24 -26 ° C. A 1% aqueous solution at 5-6°C decomposes 2, 5, and 9% in 2, 8, and 24 hours respectively. At room temperature a 1% aqueous solution shows 7, 20 and 41% decomposition in 2, 8, and 24 hours respectively (UV and NMR).
P201, P202, P260, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, P501
H302
Drug Information
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
1-beta-D-arabinosyl-5-azacytosine
Azacytidine Use and Manufacturing
A mixture of 5-azacytosine (5.0 g, 44.6 mol), HMDS (6.3 mL, 29.8 mol), and TMSCl (6 mL, 47.3 mmol) in acetonitrile (78 mL) was heated to reflux for 20 hours under an inert atmosphere. TMS-triflate (9 mL, 50 mmol) and 1, 2, 3, 5-tetra-O-acetyl-β-D-ribofuranose (14.2 g, 44.6 mmol were added directly to the silylated 5-azacytosine in acetonitrile. The addition was performed at ambient temperature and under an inert atmosphere. The reaction mixture was maintained under stirring for 20 hours, then poured over a pre-cooled (0-5° C.) sodium bicarbonate solution (10percent, 500 mL). The resulting mixture was extracted with dichloromethane (3.x.75 mL). The combined organic extract was washed with cooled (0-5° C.) 10percent sodium bicarbonate (2.x.25 mL) and brine (2.x.25 mL), then dried over magnesium sulfate (10.0 g), filtered, and the filtrate concentrated in vacuum to dryness. The off-white foam dissolved in methanol (120 mL) was treated with a solution of 25percent sodium methoxide in methanol (1.0 g, 4.62 mmol). Soon a white solid started to separate. The suspension was stirred at ambient temperature for 15 hours, then the solid was filtered off, washed with methanol (3.x.5 mL) and anhydrous ether (2.x.5 mL), then dried in vacuum. The crude 5-azacytidine (4.5 g, 41.3percent) was further purified from DMSO and methanol (for details see Example 4).[00122] The latter was dissolved in MeOH (240 g) and the resulting mixture was filtered (small amount of salt).[00123] 25percent MeONaMeOH (15.4 g; 0.02 mol) dissolved in MeOH (250 g) was added over 5 min.[00124] The resulting mixture is stirred at 20-25°C for 1.5 h. The crystals were filtered and washed with MeOH (300 g).[00125] The wet solid was dried under vacuum at 60°C for 15 h to give 5-azacytidine as an off white solid.[00126] Yield: 75percent, purity >99percent area by HPLC.To a solution of 2, 3, 5-tri-O-acetyl-β-D-ribofuranose-4-amino-1, 3, 5-triazine (1.0 Kg) which is dissolved in DBU (5.0 L) was added methanol (40 L) and stirred for 6 h at 20-25 °C. Filtered the solid and washed with methanol (500 mL) and suck dried for 30 min and subjected for drying under vacuum tray drier to get crude 400 g of 4-amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one.
antianginal
Computed Properties
Molecular Weight:244.20
XLogP3:-2.2
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:244.08076950
Monoisotopic Mass:244.08076950
Topological Polar Surface Area:141
Heavy Atom Count:17
Complexity:384
Undefined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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