Related Searches: 5-Aza-2'-deoxycytidine, deoxycytidine, 2-Chloro-5-nitropyridine, 2-Bromo-5-methylpyridine, 2-Bromo-5-nitropyridine, View all

5-Aza-2'-deoxycytidine(CAS No. 2353-33-5)

5-Aza-2'-deoxycytidine C8H12N4O4 (cas 2353-33-5) Molecular Structure

2353-33-5 Structure

Identification and Related Records

【Name】
5-Aza-2'-deoxycytidine
【Iupac name】
4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,
5-triazin-2-one
【CAS Registry number】
2353-33-5
【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
【EINECS(EC#)】
219-089-4
【Molecular Formula】
C8H12N4O4 (Products with the same molecular formula)
【Molecular Weight】
228.20528
【Inchi】
InChI=1S/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
【InChIKey】
XAUDJQYHKZQPEU-KVQBGUIXSA-N
【Canonical SMILES】
C1C(C(OC1N2C=NC(=NC2=O)N)CO)O
【Isomers smiles】
C1[C@@H]([C@H](O[C@H]1N2C=NC(=NC2=O)N)CO)O
【MOL File】
2353-33-5.mol

Chemical and Physical Properties

【Appearance】
white crystalline powder
【Density】
1.9 g/cm3
【Melting Point】
200℃ (dec.)
【Boiling Point】
485.8 °C at 760 mmHg
【Vapour】
1.78E-11mmHg at 25°C
【Refractive Index】
1.779
【Flash Point】
247.6 °C
【Water】
acetic acid/water (1:1): 50 mg/mL
【Solubilities】
acetic acid/water (1:1): 50 mg/mL
【Stability】
Stable. May be light or air sensitive. Incompatible with strong oxidizing agents.
【Storage temp】
?20°C
【Computed Properties】
Molecular Weight:228.20528 [g/mol]
Molecular Formula:C8H12N4O4
XLogP3:-1.2
H-Bond Donor:3
H-Bond Acceptor:4
Rotatable Bond Count:2
Tautomer Count:3
Exact Mass:228.085855
MonoIsotopic Mass:228.085855
Topological Polar Surface Area:121
Heavy Atom Count:16
Formal Charge:0
Complexity:356
Isotope Atom Count:0
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:4
Feature 3D Ring Count:2
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:13

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R22;R36/37/38
【Safety Statements 】
S26
【Safety】

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

【Specification】

? Decitabine (CAS NO.2353-33-5), its Synonyms are 5-Aza-2'-deoxycytidine ; 2-Desoxy-5-azacytidine ; 2-deoxyazacytidine ; 4-Amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)-s-triazin-2(1H)-one ; 5-Azadeoxycytidine ; 1,3,5-Triazin-2(1H)-one, 4-amino-1-(2-deoxy-beta-D-erythro-pentofuranosyl)- . It is white crystalline powder.

Use and Manufacturing

【Usage】

 Decitabine (CAS NO.2353-33-5) is used as a drug.

Biomedical Effects and Toxicity

【Biological Activity】
Cytosine analog that once incorporated into DNA acts as a suicide substrate for DNA methyltransferase. Inhibits DNA methyltransferase and results in DNA hypomethylation and activation of silent genes. Chemotherapeutic agent; suppresses growth of human tumor cell lines. Demethylates differentiation-related genes; reverses embryonic stem cell differentiation.
【Pharmacological Action】
- Antimetabolites that are useful in cancer chemotherapy.
- Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
- An agent that causes the production of physical defects in the developing embryo.
【Therapeutic Uses】
Used as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines.
【Biomedical Effects and Toxicity】
Cytosine analog that once incorporated into DNA acts as a suicide substrate for DNA methyltransferase. Inhibits DNA methyltransferase and results in DNA hypomethylation and activation of silent genes. Chemotherapeutic agent; suppresses growth of human tumor cell lines. Demethylates differentiation-related genes; reverses embryonic stem cell differentiation.

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