CAS 320-67-2

Azacytidine

Description:

Azacytidine, with the CAS number 320-67-2, is a nucleoside analog of cytidine, characterized by the presence of a nitrogen atom in the pyrimidine ring. This modification alters its biological activity, making it a potent inhibitor of DNA methylation. Azacytidine is primarily used in the treatment of certain types of cancer, particularly myelodysplastic syndromes and acute myeloid leukemia, as it can induce differentiation and apoptosis in malignant cells. The compound is typically administered via injection and has a relatively short half-life in the body. Its mechanism of action involves incorporation into RNA and DNA, leading to hypomethylation of genes that are silenced in cancer. Azacytidine is also known for its ability to reactivate tumor suppressor genes, contributing to its therapeutic effects. However, it can cause side effects, including myelosuppression, gastrointestinal disturbances, and potential long-term risks. Overall, azacytidine represents a significant advancement in epigenetic therapy, highlighting the importance of DNA methylation in cancer treatment.

Formula: C₈H₁₂N₄O₅

InChI: 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

InChI key: InChIKey=NMUSYJAQQFHJEW-KVTDHHQDSA-N

SMILES: O[C@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C(=O)N=C(N)N=C2

Synonyms:

• 1,3,5-Triazin-2(1H)-one, 4-amino-1-β-<span class="text-smallcaps">D</span>-ribofuranosyl-
• 1,3,5-Triazin-2(1H)-one, 4-amino-1-β-D-ribofuranosyl-
• 2-(β-D-Ribofuranosyl)-4-amino-1,3,5-triazin-2-on
• 2-(β-D-ribofurannosyl)-4-amino-1,3,5-triazine-2-one
• 2-(β-D-ribofuranosil)-4-amino-1,3,5-triazin-2-ona
• 2-(β-D-ribofuranosyl)-4-amino-1,3,5-triazin-2-one
• 4-Amino-1-Beta-D-Ribofuranosyl-S-Triazin-2(1H)-On
• 4-Amino-1-β-<span class="text-smallcaps">D</span>-ribofuranosyl-1,3,5-triazin-2(1H)-one
• 4-amino-1-D-lyxofuranosyl-1,3,5-triazin-2(1H)-one
• 4-amino-1-beta-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
• 4-amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one
• 4-amino-1-pentofuranosyl-1,3,5-triazin-2(1H)-one
• 5 Azc
• 5-Ac
• 5-Azac
• 5-Azacitidine
• 5-Azcr
• 5-Triazin-2(1H)-One,4-Amino-1-Beta-D-Ribofuranosyl-3
• Antibiotic u 18496
• Antibioticu18496
• Azacitidine
• Azacytidine
• Cc 486
• Ladakamycin
• Ledakamycin
• Mylosar
• Nci-C01569
• Nsc 103-627
• Nsc-102816
• U 18496
• U18496
• Vidaza
• Wr 183027
• s-Triazin-2(1H)-one, 4-amino-1-β-<span class="text-smallcaps">D</span>-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

5-Azacytidine

CAS: 320-67-2

Formula: C₈H₁₂N₄O₅

Purity: >98.0%(T)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 244.21

Ref: 3B-A2033

5-Azacytidine, 98%

CAS: 320-67-2

Causes DNA demethylation or hemi-demethylation; a powerful mutagen

Formula: C₈H₁₂N₄O₅

Purity: 98%

Color and Shape: White to off-white, Powder or crystals or crystalline powder

Molecular weight: 244.21

Ref: 02-J64159

Azacitidine

CAS: 320-67-2

Nucleic acids and their salts, whether or not chemically defined; other heterocyclic compounds, nesoi

Formula: C₈H₁₂N₄O₅

Color and Shape: White Off-White Powder

Molecular weight: 244.08077

Ref: 45-1045520

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

CAS: 320-67-2

Formula: C₈H₁₂N₄O₅

Purity: 98%

Color and Shape: Solid

Molecular weight: 244.2047

Ref: IN-DA003824

5-Azacytidine

CAS: 320-67-2

5-Azacytidine (Ladakamycin) is a cytidine nucleoside analog, a DNA methylation inhibitor with specificity.

Formula: C₈H₁₂N₄O₅

Purity: 98% - 99.79%

Color and Shape: Crystals From Methanol Physical Description White Crystalline Powder (Ntp 1992)

Molecular weight: 244.2

Ref: TM-T1339

Azacitidine

CAS: 320-67-2

Formula: C₈H₁₂N₄O₅

Color and Shape: White To Off-White Solid

Molecular weight: 244.21

Ref: 4Z-A-811

5-Azacytidine

CAS: 320-67-2

5-Azacytidine

Purity: ≥98%

Molecular weight: 244.2g/mol

Ref: 54-BUP15112

5-Azacytidine

CAS: 320-67-2

5-Azacytidine

Purity: 98%

Molecular weight: 244.20g/mol

Ref: 54-OR1011812

Azacitidine Impurity 3

CAS: 320-67-2

Formula: C₁₄H₁₈N₄O₈

Color and Shape: Off-White Solid

Molecular weight: 370.32

Ref: 4Z-A-8110

5-Azacytidine

CAS: 320-67-2

Formula: C₈H₁₂N₄O₅

Purity: ≥ 98.0% (dried basis)

Color and Shape: White to off-white crystalline powder

Molecular weight: 244.20

Ref: 7W-GA4671

Azacitidine

Controlled Product

CAS: 320-67-2

Formula: C₈H₁₂N₄O₅

Color and Shape: Off-White

Molecular weight: 244.20

Ref: 86-MM1259.00

5-Azacytidine

CAS: 320-67-2

Applications A potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase.
References Kusaba, H., et al.: Eur. J. Biochem., 262, 924 (1999), Broday, L., et al.: Mol. Cell Biol., 19, 3198 (1999), Qian, X., et al.: Am. J. Pathol., 153, 1475 (1999), Canova, C., et al.: Mech. Ageing Dev., 101, 153 (1998)

Formula: C₈H₁₂N₄O₅

Color and Shape: Off-White

Molecular weight: 244.20

Ref: TR-A796000

5-Azacytidine-15N4

Controlled Product

CAS: 320-67-2

Applications Labelled Azacytidine (A796000), a potent growth inhibitor and cytotoxic agent. It acts as a demethylating agent by inhibiting DNA methyltransferase.
References Kusaba, H., et al.: Eur. J. Biochem., 262, 924 (1999), Broday, L., et al.: Mol. Cell Biol., 19, 3198 (1999), Qian, X., et al.: Am. J. Pathol., 153, 1475 (1999), Canova, C., et al.: Mech. Ageing Dev., 101, 153 (1998)

Formula: C₈H₁₂₁₅N₄O₅

Color and Shape: White To Off-White

Molecular weight: 248.18

Ref: TR-A796002

5-Azacytidine

CAS: 320-67-2

An azanucleoside and epigenetic modulator that interferes with nucleic acid metabolism. The compound gets incorporated into RNA and inhibits ribonucleotide reductase subunit RRM2 in leukemia cell lines. Intracellularly, 5-azacytidine can get converted into 2′-deoxy-5-azacytidine (decitabine) and subsequently incorporated in DNA, where it irreversibly inhibits DNMT1 methyltransferase. In human epithelial cell lines, this compound decreases Src-activated expression of a histone chaperone CAF1 and inhibits cell motility and invasiveness.

Formula: C₈H₁₂N₄O₅

Purity: Min. 95%

Color and Shape: White Off-White Powder

Molecular weight: 244.21 g/mol

Ref: 3D-NA02947

5-Azacytidine

CAS: 320-67-2

Formula: C₈H₁₂N₄O₅

Purity: 98%

Color and Shape: Solid

Molecular weight: 244.207

Ref: 10-F492447

5-Azacytidine extrapure, 98%

CAS: 320-67-2

Formula: C₈H₁₂N₄O₅

Purity: min. 98%

Color and Shape: White to off-white, Crystalline powder

Molecular weight: 244.21

Ref: SR-34476