Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C14H25N4O11P2.Na |
Molecular Weight | 510.3058 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].C[N+](C)(C)CCOP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=CC(N)=NC2=O
InChI
InChIKey=YWAFNFGRBBBSPD-OCMLZEEQSA-M
InChI=1S/C14H26N4O11P2.Na/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);/q;+1/p-1/t9-,11-,12-,13-;/m1./s1
Molecular Formula | C14H25N4O11P2 |
Molecular Weight | 487.316 |
Charge | -1 |
Count |
|
Stereochemistry | EPIMERIC |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Citicoline (CDP-choline; cytidine 5'-diphosphocholine) is a novel nutrient with a broad spectrum of benefits for conditions associated with symptoms of neurological dysfunction shows promise of clinical efficacy in elderly patients with cognitive deficits, inefficient memory, and early-stage Alzheimer's disease. Citicoline has also been investigated as a therapy in stroke patient. Despite it was approved in some countries for treatment Traumatic Brain Injury (TBI), the use of this drug for acute TBI seems to have no field of support anymore, whereas it may have some benefits in improving the neuro-cognitive state in chronic TBI patients. It's also recommended to keep in mind acute interventions like Psychological First Aid (PFA) during acute TBI management. Citicoline plays several important roles in human physiology, including enhancement of structural integrity and signaling for cell membranes, support of acetylcholine synthesis, and synthesis of betaine, a methyl donor. The precise mechanism of action of Citicoline to treat disease is unknown, but was confirmed, that drug might increase phosphatidylcholine (PtdCho) synthesis and might reverse PtdCho loss. In addition, was shown, that citicoline modulates phospholipids metabolism and neurotransmitter levels and appears to improve cognition in some central nervous system disorders such as bipolar disorder and cocaine dependence. Bipolar disorder is associated with the highest rates of substance abuse of any psychiatric disorder. Cocaine use is particularly common in patients with bipolar disorder.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: phosphatidylcholine Sources: https://www.ncbi.nlm.nih.gov/pubmed/12021827 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Selective accumulation of cytosol CDP-choline as an isolated erythrocyte defect in chronic hemolysis. | 1983 May |
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Memory effects of the new derivative of the p-chlorophenoxyacetic acid adafenoxate compared to the effects of some cognition-enhancing drugs in rats. | 1989 Sep |
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Effects of citicholine and of the combination citicholine + piracetam on the memory (experiments on mice). | 1990 |
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Efficacy of CDP-choline in the treatment of senile alterations in memory. | 1991 |
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Metabolism and actions of CDP-choline as an endogenous compound and administered exogenously as citicoline. | 1995 |
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Citicoline improves memory performance in elderly subjects. | 1997 Apr |
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A family with chronic haemolysis and selective accumulation of erythrocyte CDP-choline. | 1997 Aug |
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A randomized dose-response trial of citicoline in acute ischemic stroke patients. Citicoline Stroke Study Group. | 1997 Sep |
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Cytidine-5'-diphosphocholine improves visual acuity, contrast sensitivity and visually-evoked potentials of amblyopic subjects. | 1998 Feb |
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Short-term treatment with citicoline (CDP-choline) attenuates some measures of craving in cocaine-dependent subjects: a preliminary report. | 1999 Feb |
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Double-blind placebo-controlled study with citicoline in APOE genotyped Alzheimer's disease patients. Effects on cognitive performance, brain bioelectrical activity and cerebral perfusion. | 1999 Nov |
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Pharmacotherapies for cocaine dependence. | 2000 Dec |
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[Usefulness of SPECT images in helping radiologists understand brain diseases]. | 2001 Apr |
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Effects of short-term citicoline treatment on acute cocaine intoxication and cardiovascular effects. | 2001 Sep |
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Citicoline increases glutathione redox ratio and reduces caspase-3 activation and cell death in staurosporine-treated SH-SY5Y human neuroblastoma cells. | 2002 Dec 6 |
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Chronic citicoline increases phosphodiesters in the brains of healthy older subjects: an in vivo phosphorus magnetic resonance spectroscopy study. | 2002 May |
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Elevated erythrocyte CDP-choline levels associated with beta-thalassaemia in patients with transfusion independent anaemia. | 2004 Oct |
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Effects of simvastatin on the expression of intercellular adhesion molecule-1 mRNA in neonatal brain with hypoxic-ischemic damage. | 2005 Aug |
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Cytidine 5'-diphosphocholine (CDP-choline) in stroke and other CNS disorders. | 2005 Jan |
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The late negative episodic memory effect: the effect of recapitulating study details at test. | 2005 May |
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Effects of citicoline on experimental spinal cord injury. | 2005 Nov |
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A randomized, placebo-controlled trial of citicoline add-on therapy in outpatients with bipolar disorder and cocaine dependence. | 2007 Oct |
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Dual roles of brain serine hydrolase KIAA1363 in ether lipid metabolism and organophosphate detoxification. | 2008 Apr 1 |
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Neurochemical alterations in methamphetamine-dependent patients treated with cytidine-5'-diphosphate choline: a longitudinal proton magnetic resonance spectroscopy study. | 2010 Apr |
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Citicoline (CDP-choline) increases Sirtuin1 expression concomitant to neuroprotection in experimental stroke. | 2013 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00545662
1000 mg twice a day orally or enterally. The first dose is within 24 hours of injury and treatment continues for 90-days or until the 90-day outcome assessment.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23227823
Citicoline induces angiogenesis improving survival of vascular/human brain microvessel endothelial cells (EC) through pathways involving ERK1/2 and insulin receptor substrate-1. hCMEC/D3 cells were seeded at a concentration of 8 × 104 cells/ml in 500 μl of complete basal medium in each well of 24-well plate. After 4 h, the medium was changed to serum-poor medium (SPM) containing 1% FBS containing different concentrations of citicoline (1 μM, 10 μM and 100 μM; NOTE; pilot experiments were carried out using 1-100 μM citicoline and optimized for the use of 10 μM subsequently as this produced the most prominent responses). It was discovered that insulin receptor substrate-1 (IRS-1) represented a potent modulator of pro-angiogenic signalling cascades in vascular EC, thus was shown that citicoline induces phosphorylation of IRS-1 and concomitant EC activation and increased vascularisation, that could be a key novel mechanism of action of citicoline.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 15:22:17 GMT 2023
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Record UNII |
7XQ5AKD9YD
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Record Status |
Validated (UNII)
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Record Version |
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