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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
Structure of CITICOLINE SODIUM

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

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Selective accumulation of cytosol CDP-choline as an isolated erythrocyte defect in chronic hemolysis.
1983 May
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
Effects of citicholine and of the combination citicholine + piracetam on the memory (experiments on mice).
1990
Efficacy of CDP-choline in the treatment of senile alterations in memory.
1991
Metabolism and actions of CDP-choline as an endogenous compound and administered exogenously as citicoline.
1995
Citicoline improves memory performance in elderly subjects.
1997 Apr
A family with chronic haemolysis and selective accumulation of erythrocyte CDP-choline.
1997 Aug
A randomized dose-response trial of citicoline in acute ischemic stroke patients. Citicoline Stroke Study Group.
1997 Sep
Cytidine-5'-diphosphocholine improves visual acuity, contrast sensitivity and visually-evoked potentials of amblyopic subjects.
1998 Feb
Short-term treatment with citicoline (CDP-choline) attenuates some measures of craving in cocaine-dependent subjects: a preliminary report.
1999 Feb
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
Pharmacotherapies for cocaine dependence.
2000 Dec
[Usefulness of SPECT images in helping radiologists understand brain diseases].
2001 Apr
Effects of short-term citicoline treatment on acute cocaine intoxication and cardiovascular effects.
2001 Sep
Citicoline increases glutathione redox ratio and reduces caspase-3 activation and cell death in staurosporine-treated SH-SY5Y human neuroblastoma cells.
2002 Dec 6
Chronic citicoline increases phosphodiesters in the brains of healthy older subjects: an in vivo phosphorus magnetic resonance spectroscopy study.
2002 May
Elevated erythrocyte CDP-choline levels associated with beta-thalassaemia in patients with transfusion independent anaemia.
2004 Oct
Effects of simvastatin on the expression of intercellular adhesion molecule-1 mRNA in neonatal brain with hypoxic-ischemic damage.
2005 Aug
Cytidine 5'-diphosphocholine (CDP-choline) in stroke and other CNS disorders.
2005 Jan
The late negative episodic memory effect: the effect of recapitulating study details at test.
2005 May
Effects of citicoline on experimental spinal cord injury.
2005 Nov
A randomized, placebo-controlled trial of citicoline add-on therapy in outpatients with bipolar disorder and cocaine dependence.
2007 Oct
Dual roles of brain serine hydrolase KIAA1363 in ether lipid metabolism and organophosphate detoxification.
2008 Apr 1
Neurochemical alterations in methamphetamine-dependent patients treated with cytidine-5'-diphosphate choline: a longitudinal proton magnetic resonance spectroscopy study.
2010 Apr
Citicoline (CDP-choline) increases Sirtuin1 expression concomitant to neuroprotection in experimental stroke.
2013 Sep
Patents

Sample Use Guides

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
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
by admin
on Fri Dec 15 15:22:17 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:17 GMT 2023
Record UNII
7XQ5AKD9YD
Record Status Validated (UNII)
Record Version
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Name Type Language
CITICOLINE SODIUM
MART.   USAN   WHO-DD  
USAN  
Official Name English
CHOLINE HYDROXIDE, 5'-ESTER WITH CYTIDINE 5'-(SODIUM DIHYDROGEN DIPHOSPHATE), INNER SALT
Common Name English
CYTIDINE 5'-(TRIHYDROGEN DIPHOSPHATE), P'-(2-(TRIMETHYLAMMONIO)ETHYL) ESTER, INNER SALT, MONOSODIUM SALT
Common Name English
Citicoline sodium [WHO-DD]
Common Name English
IP-302 SODIUM
Code English
IP 302 SODIUM
Code English
CERAXON
Brand Name English
CITICOLINE SODIUM [USAN]
Common Name English
CITICOLINE SODIUM SALT [MI]
Common Name English
CITICOLINE SODIUM SALT
MI  
Common Name English
CITICOLINE SODIUM [USP-RS]
Common Name English
CITICOLINE SODIUM [MART.]
Common Name English
Code System Code Type Description
RS_ITEM_NUM
1134305
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID4048981
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
SMS_ID
100000092641
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL1618340
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
CAS
33818-15-4
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
NCI_THESAURUS
C171765
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
RXCUI
1099914
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY RxNorm
DRUG BANK
DBSALT002146
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
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FDA UNII
7XQ5AKD9YD
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
ECHA (EC/EINECS)
251-689-1
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
MERCK INDEX
m3588
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY Merck Index
EVMPD
SUB01321MIG
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
PUBCHEM
36605
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
USAN
GG-60
Created by admin on Fri Dec 15 15:22:17 GMT 2023 , Edited by admin on Fri Dec 15 15:22:17 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY