Structure via PubChem · Public domain (PubChem)
citicoline
Sign in to saveAlso known as 5'-O-[hydroxy({[2-(trimethylammonio)ethoxy]phosphinato}oxy)phosphoryl]cytidine, cytidine 5'-(trihydrogen diphosphate), P'-[2-(trimethylammonio)ethyl] ester, inner salt, cytidine 5'-diphosphocholine, CDP-choline (neutral charge), CDP-choline
Citicoline (INN), also known as cytidine diphosphate-choline (CDP-choline) or '''cytidine 5'-diphosphocholine''' is an intermediate in the generation of phosphatidylcholine from choline, a common biochemical process in cell membranes. Citicoline is naturally occurring in the cells of human and animal tissue, in particular the organs.
Chemical data
- Formula
- C14H26N4O11P2
- Molecular weight
- 488.32 g/mol
- IUPAC name
- [[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] 2-(trimethylazaniumyl)ethyl phosphate
- 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
- InChIKey
- RZZPDXZPRHQOCG-OJAKKHQRSA-N
- XLogP
- -4
- Polar surface area
- 214 Ų
- H-bond donors
- 4
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
~8 min read
Encyclopedic overview
17 sectionsContents
- Use as a dietary supplement
- Research
- Ischemic stroke
- Vision
- Mechanism of action
- Neuroprotective effects
- Neuronal membrane
- Cell signalling
- Glutamate transport
- Pharmacokinetics
- Side effects
- Synthesis
- In vivo
- Society and culture
- Recreational use
- See also
- References
{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 449576702 | IUPAC_name = 5'-O-[hydroxy({hydroxy[2-(trimethylammonio)ethoxy]phosphoryl}oxy)phosphoryl]cytidine | image = Citicoline.svg | image_class = skin-invert-image | image2 = CDP-Choline_3D_Xtal_balls.png | image_class2 = bg-transparent | width2 = 280 | tradename = Neurocoline | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = OTC | legal_status = | routes_of_administration = oral | bioavailability = 90% oral | protein_bound = | metabolism = | elimination_half-life = | excretion = respiration (as CO2) and urine | CAS_number_Ref = | CAS_number = 987-78-0 | ATC_prefix = N06 | ATC_suffix = BX06 | DrugBank_Ref = | DrugBank = | ChEBI_Ref = | ChEBI = 16436 | ChEMBL_Ref = | ChEMBL = 1618340 | UNII_Ref = | UNII = 536BQ2JVC7 | KEGG_Ref = | KEGG = D00057 | PubChem = 11583971 | ChemSpiderID_Ref = | ChemSpiderID = 13207 | C = 14 | H = 27 | N = 4 | O = 11 | P = 2 | charge = + | smiles = C[N+](C)(C)CCOP(=O)([O-])OP(=O)(O)OC[C@@H]1[C@@H](O)[C@@H](O)[C@@H](O1)N2C=CC(N)=NC2=O | StdInChI_Ref = | StdInChI = 1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1 | StdInChIKey_Ref = | StdInChIKey = RZZPDXZPRHQOCG-OJAKKHQRSA-N | synonyms = Cytidine diphosphate choline | drug_name = | width = 250 | alt = | caption = | type = | MedlinePlus = | licence_EU = | licence_US = }} Citicoline (INN), also known as cytidine diphosphate-choline (CDP-choline) or '''cytidine 5'-diphosphocholine''' is an intermediate in the generation of phosphatidylcholine from choline, a common biochemical process in cell membranes. Citicoline is naturally occurring in the cells of human and animal tissue, in particular the organs.
==Use as a dietary supplement== Citicoline is available as a supplement in over 70 countries under a variety of brand names: CereBleu, Cebroton, Ceraxon, Cidilin, Citifar, Cognizin, Difosfocin, Hipercol, NeurAxon, Nicholin, Sinkron, Somazina, Synapsine, Startonyl, Trausan, Xerenoos, etc. When taken as a supplement, citicoline is hydrolyzed into choline and cytidine in the intestine. Once these cross the blood–brain barrier, they are reformed into citicoline by the rate-limiting enzyme in phosphatidylcholine synthesis, CTP-phosphocholine cytidylyltransferase.
Excerpted from Wikipedia’s “citicoline” article, available under the CC BY-SA 4.0 licence.