Decitabine

Base Information

• Chemical Name: Decitabine
• CAS No.: 2353-33-5
• Deprecated CAS: 123795-43-7,105597-46-4
• Molecular Formula: C₈H₁₂N₄O₄
• Molecular Weight: 228.208
• Hs Code.: 29349990
• European Community (EC) Number: 219-089-4,815-973-4
• UNII: 776B62CQ27
• DSSTox Substance ID: DTXSID7030432
• Nikkaji Number: J91.053H
• Wikipedia: Decitabine
• Wikidata: Q1181878
• NCI Thesaurus Code: C981
• RXCUI: 15657
• Pharos Ligand ID: 7FVQT3S3U719
• Metabolomics Workbench ID: 43468
• ChEMBL ID: CHEMBL1201129
• Mol file: 2353-33-5.mol

Synonyms:2' 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

Chemical Property of Decitabine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: ~200 °C (dec.)
• Refractive Index: 1.6590 (estimate)
• Boiling Point: 485.8 °C at 760 mmHg
• PKA: 14.02±0.60(Predicted)
• Flash Point: 247.6 °C
• PSA: 123.49000
• Density: 1.9 g/cm³
• LogP: -1.55760
• Storage Temp.: −20°C
• Solubility.: acetic acid/water (1:1): 50 mg/mL
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 228.08585488
• Heavy Atom Count: 16
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

Decitabine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi,T
• Statements: 22-36/37/38-68-61
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: C1C(C(OC1N2C=NC(=NC2=O)N)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](O[C@H]1N2C=NC(=NC2=O)N)CO)O
• Recent ClinicalTrials: Roll-over Study for Patients Who Have Completed a Prior Novartis-sponsored Sabatolimab (MBG453) Study and Are Judged by the Investigator to Benefit From Continued Treatment With Sabatolimab.
• Recent EU Clinical Trials: A multicentre trial evaluating the efficacy and safety of oral decitabine-tetrahydrouridine (NDec) in patients with sickle cell disease
• Recent NIPH Clinical Trials: DACTBT-P1/P2
• Description: Decitabine, 5-aza-2’-deoxycytidine, has been launched for the treatment of myelodysplastic syndromes (MDS). MDS are a set of hematologic disorders affecting the bone marrow that result in ineffective formation and development of blood cells. Furthermore, patients with MDS have a high risk of progressing to acute myeloid leukemia (AML). Traditional treatments include blood transfusions, hematopoietic growth factors, and prophylactic antibiotics, but these measures merely improve the quality of life with questionable effects on disease modification. While stem-cell transplantation is an aggressive, potentially curative approach, the advanced age or the other complicating health issues of most patients preclude them from considering this option. Recent advances in the underlying etiology of MDS, however, have led to the development of a new class of compounds known as ‘‘demethylating agents’’. Decitabine follows the successful introduction of the first DNA methyltransferase inhibitor azacitidine.
• Uses: 5-Aza-2′-deoxycytidine has been used as a demethylating agent in breast cancer cell line, chromatin, DNA and promoter region of p16 gene. Used as cancer treatment, in particular to inhibit the growth of pancreatic endocrine tumor cell lines. Decitabine is a potent inhibitor of DNA methylation with IC50 of 438 nM and 4.38 nM in HL-60 and KG1a cells, respectively
• Clinical Use: Antineoplastic antimetabolite agent:Treatment of acute myeloid leukaemia
• Drug interactions: Potentially hazardous interactions with other drugsAntipsychotics: avoid with clozapine, increased risk of agranulocytosis.

Technology Process of Decitabine

There total 25 articles about Decitabine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(3,5-di-O-p-chlorobenzoyl-2-deoxy-β-D-ribofuranosyl)-5-azacytosine (1034301-08-0) → 5-aza-2'-deoxycytidine (2353-33-5,22432-95-7)

Guidance literature:

With ammonia; Alcoholic medium;

Reference yield: 89.3%

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine (52523-35-0) + 1-chloro-2-deoxy-D-ribofuranose (80184-05-0) → 5-aza-2'-deoxycytidine (2353-33-5,22432-95-7)

Guidance literature:

1-chloro-2-deoxy-D-ribofuranose; With cobalt(II) nitrate; 1,1'-bi-2-naphthol; In N,N-dimethyl-formamide; at 60 ℃; Inert atmosphere;

2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine; With triethylamine; In N,N-dimethyl-formamide; at 40 ℃; Temperature; Concentration; Reagent/catalyst;

Reference yield: 78.5%

1-<3,5-bis(Fmoc)-2'-deoxyribofuranosyl>-5-azacytidine → 5-aza-2'-deoxycytidine (2353-33-5,22432-95-7)

Guidance literature:

With pyridine; triethylamine; at 20 ℃; for 2h;

upstream raw materials:

N-(formylamidino)-N'-β-D-2-deoxyribofuranosylurea

decitabine monohydrate

5-azacytosine

3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride

Downstream raw materials:

5-aza-2'-deoxycytidine

5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-5-azacytidine

guadecitabine sodium salt

guadecitabine triethylammonium salt

Refernces

• 1、 -. "Decitabine intermediate compound VI". . . Retrieved 2021/01/24.
• 2、 -. "Preparation method of decitabine". Paragraph 0010; 0035; 0037-0038; 0040-0041; 0043-0044; 0046. . Retrieved 2021/01/15.