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5-Aza-2'-deoxycytidine

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Name

5-Aza-2'-deoxycytidine

EINECS 219-089-4
CAS No. 2353-33-5 Density 1.9 g/cm3
PSA 123.49000 LogP -1.55760
Solubility acetic acid/water (1:1): 50 mg/mL Melting Point ~200 °C (dec.)
Formula C8H12N4O4 Boiling Point 485.8 °C at 760 mmHg
Molecular Weight 228.208 Flash Point 247.6 °C
Transport Information N/A Appearance white crystalline powder
Safety 26-36 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 2353-33-5 (5-Aza-2'-deoxycytidine) Hazard Symbols HarmfulXn,IrritantXi
Synonyms

s-Triazin-2(1H)-one,4-amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-(7CI,8CI);2-Desoxy-5-azacytidine;2'-Deoxy-5-azacytidine;5-Azadeoxycytidine;DAC;Dacogen;1,3,5-Triazin-2(1H)-one,4-amino-1-(2-deoxy-b-D-erythro-pentofuranosyl)-;b-Decitabine;decitabine;

Article Data 30

5-Aza-2'-deoxycytidine Specification

1. Introduction of 5-Aza-2'-deoxycytidine

5-Aza-2'-deoxycytidine is one kind of white crystalline powder. Its IUPAC Name is 4-Amino-1-[4-hydroxy-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; Mutation data; Noxae; Reproductive Effect; Teratogens.
It belongs to API; Bases & Related Reagents; Nucleotides; analog of cytosine. 5-Aza-2'-deoxycytidine can soluble in acetic acid/water (1:1): 50 mg/mL.

2. Properties of 5-Aza-2'-deoxycytidine

Physical properties about 5-Aza-2'-deoxycytidine are:
(1)Index of Refraction: 1.779; (2)Molar Refractivity: 50.23 cm3; (3)Molar Volume: 119.7 cm3; (4)Surface Tension: 91.7 dyne/cm; (5)Density: 1.9 g/cm3; (6)Flash Point: 247.6 °C; (7)Enthalpy of Vaporization: 86.58 kJ/mol; (8)Boiling Point: 485.8 °C at 760 mmHg; (9)Melting Point: -200 °C (dec.); (10)storage temperature: -20 °C; (11)Solubility: acetic acid/water (1:1): 50 mg/mL; (12)Stability: Stable. May be light or air sensitive. Incompatible with strong oxidizing agents; (13)Vapour Pressure of Decitabine (CAS NO.2353-33-5): 1.78E-11 mmHg at 25 °C.

3. Structure Descriptors of 5-Aza-2'-deoxycytidine

(1) SMILES: O=C1/N=C(\N=C/N1[C@@H]2O[C@@H]([C@@H](O)C2)CO)N Copy;
(2)InChI: InChI=1/C8H12N4O4/c9-7-10-3-12(8(15)11-7)6-1-4(14)5(2-13)16-6/h3-6,13-14H,1-2H2,(H2,9,11,15)/t4-,5+,6+/m0/s1;
(3)Std. InChIKey: XAUDJQYHKZQPEU-KVQBGUIXSA-N.

4. Toxicity of 5-Aza-2'-deoxycytidine

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 190mg/kg (190mg/kg)   Cancer Research. Vol. 37, Pg. 3684, 1977.
mouse LD50 intravenous 22mg/kg (22mg/kg) BLOOD: LEUKOPENIA

BLOOD: THROMBOCYTOPENIA
Drug and Chemical Toxicology. Vol. 4, Pg. 373, 1981.

5. Safety information of 5-Aza-2'-deoxycytidine

Poison by intravenous route. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS of Decitabine (CAS NO.2353-33-5): XZ3012000

6. Uses of 5-Aza-2'-deoxycytidine

Decitabine (CAS NO.2353-33-5) is used as a drug. It can be used as as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines. 5-Aza-2'-deoxycytidine is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

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