Citicoline sodium

Base Information

• Chemical Name: Citicoline sodium
• CAS No.: 33818-15-4
• Molecular Formula: C14H25N4NaO11P2
• Molecular Weight: 510.31
• Hs Code.: 29349990
• European Community (EC) Number: 251-689-1,213-580-7
• UNII: 7XQ5AKD9YD
• DSSTox Substance ID: DTXSID4048981
• Wikipedia: Citicoline
• Wikidata: Q27268988
• NCI Thesaurus Code: C171765
• ChEMBL ID: CHEMBL1256994
• Mol file: 33818-15-4.mol

Synonyms:5'-Diphosphocholine, Cytidine;CDP Choline;Choline, CDP;Choline, Cytidine Diphosphate;Cidifos;Citicholine;Citicoline;Cyticholine;Cytidine 5' Diphosphocholine;Cytidine 5'-Diphosphocholine;Cytidine Diphosphate Choline;Diphosphate Choline, Cytidine

Chemical Property of Citicoline sodium

Chemical Property:

• Appearance/Colour: white solid
• Melting Point: 259-268°C (dec.)
• PSA: 238.17000
• LogP: -0.14090
• Storage Temp.: 2-8°C
• Solubility.: H2O: 100mg/mL
• Water Solubility.: Soluble in water (100 mg/ml).
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 510.08927590
• Heavy Atom Count: 32
• Complexity: 813

Purity/Quality:

98% ^*data from raw suppliers

Citicoline Sodium Salt ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[N+](C)(C)CCOP(=O)([O-])OP(=O)([O-])OCC1C(C(C(O1)N2C=CC(=NC2=O)N)O)O.[Na+]
• Isomeric SMILES: C[N+](C)(C)CCOP(=O)([O-])OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O.[Na+]
• Description: Citicoline is a nucleic acid derivatives, Geiger found that citicoline can restore brain injury in the animal experiments in 1956. Kennedy study confirmed that citicoline can make brain injury recovery in 1957. Takeda pharmaceutical company in Japan developed and produced it in 1961. It was registered in China in 1988, and is currently the best-selling drug among clinical brain diseases. It plays an important role in the synthesis of lecithin, by promoting the synthesis of lecithin and improving brain function. Experiments show that citicoline can enhance the levels of norepinephrine and dopamine in the central nervous system, thereby it can treat cerebrovascular disease, traumatic brain injury and cognitive impairment caused by various reasons, and there are no obvious side effects.
• Uses: Naturally occurring nucleotide; intermediate in the major pathway of lecitin biosynthesis. Neuroprotective. It is used in the treatment of ischemic stroke and head trauma. Cytidine 5′-diphosphate (CDP) is used as a substrate of CDP (nucleoside diphosphate) kinase (2.7.4.6) to produce CTP in support ofDNA and RNA biosynthesis and of ribonucleotide reductase to product dCMP. Cytidine-5'-diphosphocholine sodium salt hydrate acts as a neuroprotective agent in situations of hypoxia and ischemia. It is used as biosynthetic intermediate of membrane phospholipids. It is a cerebral vasodilator and inhibits PLA2 activation.

Technology Process of Citicoline sodium

There total 10 articles about Citicoline sodium 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: 92.54%

phosphorylcholine chloride (107-73-3) + cytidine monophosphate (63-37-6,30811-80-4) → cytidine 5'-diphosphocholine sodium salt (33818-15-4)

Guidance literature:

phosphorylcholine chloride; cytidine monophosphate; With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In acetonitrile; at 30 ℃; for 5.75h; Reflux;

With sodium hydrogencarbonate; In ethanol; at 10 - 40 ℃; for 1h; pH=7; Temperature; Reagent/catalyst; pH-value;

Reference yield: 81.7%

phosphorylcholine chloride (107-73-3) + cytidine-5'-phosphodichloride (30784-94-2) → cytidine 5'-diphosphocholine sodium salt (33818-15-4)

Guidance literature:

phosphorylcholine chloride; cytidine-5'-phosphodichloride; With triethylamine; at 0 - 25 ℃; for 24h;

With sodium hydroxide; In dichloromethane; water monomer; Reagent/catalyst;

Reference yield: 30.0%

C13H13N4O9P + phosphorylcholine chloride, calcium salt (4826-71-5) → cytidine 5'-diphosphocholine sodium salt (33818-15-4)

Guidance literature:

In acetonitrile; for 2h;

DOI:10.1002/chem.201805924

upstream raw materials:

sodium hydroxide

cytidine monophosphate

phosphorylcholine chloride, calcium salt

O^2',O^3'-carbonyl-[5']cytidylic acid

Refernces

• 1、 -. "Method for synthesizing citicoline sodium". Paragraph 0026-0027; 0029-0032; 0034-0037; 0039-0042; .... . Retrieved 2022/03/17.
• 2、 Appy, Lucie,Depaix, Ana?s,Bantreil, Xavier,Lamaty, Frédéric,Peyrottes, Suzanne,Roy, Béatrice. "Straightforward Ball-Milling Access to Dinucleoside 5′,5′-Polyphosphates via Phosphorimidazolide Intermediates". supporting information. p. 2477 - 2481. Retrieved 2019/01/29.