Welcome: Chemsynlab ,carbohydrate chemistry
Language: Chinese ∷  English

2353-33-5, Decitabine, CAS: 2353-33-5

2353-33-5, Decitabine,
CAS: 2353-33-5
C8H12N4O4 / 228.21
MFCD00043011

Decitabine, 地西他滨

5-Aza-2'-deoxycytidine

A synthetic cytosine analogue that incorporates into DNA and prevents DNA methylation via DNA (cytosine-5)-methyltransferase 1 (DNMT1) inhibition. Demonstrated potent anti-leukaemic effects attributed to cell cycle arrest and induction of apoptosis. Has anti-growth effects on solid tumor cell lines.

5-Azacytidine is an analog of cytidine which can be incorporated into DNA, inhibit DNA methyltransferases, and cause hypomethylation of cytosine residues in the absence of any significant mutagenic effects. Decitabine is a 2’-deoxy analog of 5-azacytidine which similarly causes hypomethylation of DNA by inhibiting DNA methyltransferases in a concentration-dependent manner. This action is useful in conditions characterized by DNA hypermethylation, as is found in myelodysplastic syndromes.

Decitabine is a cytidine antimetabolite analogue with potential antineoplastic activity. Decitabine incorporates into DNA and inhibits DNA methyltransferase, resulting in hypomethylation of DNA and intra-S-phase arrest of DNA replication. (NCI04)

Decitabine is a cytosine analogue and an intravenously administered antineoplastic agent used in the therapy of myelodysplastic syndromes. Decitabine is associated with a low rate of transient serum enzyme elevations during therapy, but has not been implicated in causing clinically apparent liver injury with jaundice.

Decitabine, also known as dacogen or azadc compound, belongs to the class of organic compounds known as triazinones. Triazinones are compounds containing a triazine ring which bears a ketone group a carbon atom. Decitabine is a drug which is used for treatment of patients with myelodysplastic syndromes (mds) including previously treated and untreated, de novo and secondary mds of all french-american-british subtypes (refractory anemia, refractory anemia with ringed sideroblasts, refractory anemia with excess blasts, refractory anemia with excess blasts in transformation, and chronic myelomonocytic leukemia) and intermediate-1, intermediate-2, and high-risk international prognostic scoring system groups (scores ≥0. 5). Decitabine is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Decitabine has been detected in multiple biofluids, such as urine and blood. Within the cell, decitabine is primarily located in the cytoplasm.

Title: Decitabine

CAS Registry Number: 2353-33-5

CAS Name: 4-Amino-1-(2-deoxy-b-erythro-pentofuranosyl)-1,3,5-triazin-2(1H)-one

Additional Names: 5-aza-2'-deoxycytidine

Manufacturers' Codes: NSC-127716

Trademarks: Dacogen (SuperGen)

Molecular Formula: C8H12N4O4

Molecular Weight: 228.21

Percent Composition: C 42.10%, H 5.30%, N 24.55%, O 28.04%

Literature References: Pyrimidine analog that inhibits DNA methylation and induces differentiation of leukemic cells. Prepn: J. Pliml, F. Sorm, Collect. Czech. Chem. Commun. 29, 2576 (1964); A. Piskala, F. Sorm, in Nucleic Acid Chemistry Part 1 (Wiley, New York, 1978) pp 443-449. Improved synthesis: J. Ben-Hattar, J. Jiricny, Nucleosides Nucleotides 6, 393 (1987). Chemical stability in soln: K.-T. Lin et al., J. Pharm. Sci. 70, 1228 (1981). HPLC determn in plasma: eidem, J. Chromatogr. 345, 162 (1985). Clinical trial in chronic myelogenous leukemia: H. M. Kantarjian et al., Cancer 98, 522 (2003). Review of pharmacology and mechanism of action: R. L. Momparler, Pharmacol. Ther. 30, 287-299 (1985); idem et al., Leukemia 11, Suppl. 1, 1-6 (1997); of clinical experience: B. T. Hennessy et al., Expert. Opin. Invest. Drugs 12, 1985-1993 (2003).

Properties: Crystals from methanol, mp 201-202° (dec). [a]D22 +68.5° (30 min) ® +57.8° (6 hr) (c = 0.5 in water). uv max (pH 7): 244 nm (log e 3.86). LD50 in mice (mg/kg): 190 i.p. (Momparler, 1985).

Melting point: mp 201-202° (dec)

Optical Rotation: [a]D22 +68.5° (30 min) ® +57.8° (6 hr) (c = 0.5 in water)

Absorption maximum: uv max (pH 7): 244 nm (log e 3.86)

Toxicity data: LD50 in mice (mg/kg): 190 i.p. (Momparler, 1985)

Therap-Cat: Antineoplastic.

Keywords: Antineoplastic; Antimetabolites; Pyrimidine Analogs.

CAS Number2353-33-5
Product NameDecitabine
IUPAC Name4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
Molecular FormulaC8H12N4O4
Molecular Weight228.21 g/mol
InChIInChI=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
InChI KeyXAUDJQYHKZQPEU-JKUQZMGJSA-N
SMILESC1C(C(OC1N2C=NC(=NC2=O)N)CO)O
SolubilitySparingly soluble
5.50e+00 g/L
Synonyms2' Deoxy 5 azacytidine, 2'-deoxy-5-azacytidine, 5 Aza 2' deoxycytidine, 5 Azadeoxycytidine, 5 Deoxyazacytidine, 5-aza-2'-deoxycytidine, 5-AzadC, 5-azadeoxycytidine, 5-deoxyazacytidine, 5AzadC, AzadC compound, Compound, AzadC, Dacogen, decitabine, decitabine mesylate, Mesylate, Decitabine, NSC 127716, NSC-127716, NSC127716
Canonical SMILESC1C(C(OC1N2C=NC(=NC2=O)N)CO)O
Isomeric SMILESC1[C@@H]([C@H](O[C@H]1N2C=NC(=NC2=O)N)CO)O


CAS No: 2353-33-5 Synonyms: Decitabine4-Amino-1-(2-deoxy-b-D-ribofuranosyl)-1,3,5-triazin-2(1H)-one5-Aza-2'-deoxy-D-cytidine2′-Deoxy-5-azacytidine MDL No: MFCD00043011 Chemical Formula: C8H12N4O4 Molecular Weight: 228.21

COA:

Name: Decitabine  CAS2353-33-5     M.F.: C8H12N4O4      M.W.: 228.21  

Items

Standards

Results

Appearance

White crystalline powder

Positive

NMR and MS

Should comply

Complies

Identification

IR and TLC

Positive

M.P.

199 - 203

200 - 202

Loss Weight On Dryness

Max. 0.2%

0.12%

Residue On Ignition

Max. 0.2%

0.02%

Heavy metal

Max. 20ppm

Complies

Assay (HPLC)

Min. 98%

99.6%

References:

1. Wijermans P, Lubbert M, Verhoef G, et al., J. Clin. Onc. 2000, Vol18, Pt5, p956-962


INQUIRY

Scan the qr codeClose
the qr code