Citicoline

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Citicoline is an endogenous intermediate in the formation of phosphatidylcholine from choline which is thought to have neuroprotective effects.

Generic Name
Citicoline
DrugBank Accession Number
DB12153
Background

Citicoline is a donor of choline in biosynthesis of choline-containing phosphoglycerides. It has been investigated for the treatment, supportive care, and diagnosis of Mania, Stroke, Hypomania, Cocaine Abuse, and Bipolar Disorder, among others.

Type
Small Molecule
Groups
Approved, Experimental
Structure
Thumb
Weight
Average: 488.324
Monoisotopic: 488.107330718
Chemical Formula
C14H26N4O11P2
Synonyms
  • CDP-choline
  • CDP-colina
  • citicolina
  • Citicoline
  • citidin difosfato de colina
  • Cytidine 5'-(choline diphosphate)
  • Cytidine 5'-(cholinyl pyrophosphate)
  • Cytidine 5'-diphosphocholine
  • Cytidine 5'-diphosphoric choline
  • Cytidine-5'-diphosphocholine

Pharmacology

Indication

Not Available

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ULicC proteinNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Citicoline sodium7XQ5AKD9YD33818-15-4YWAFNFGRBBBSPD-OCMLZEEQSA-M

Categories

ATC Codes
N06BX06 — Citicoline
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine ribonucleotides
Direct Parent
Pyrimidine ribonucleoside diphosphates
Alternative Parents
Pentose phosphates / Glycosylamines / Phosphocholines / Monosaccharide phosphates / Organic pyrophosphates / Pyrimidones / Aminopyrimidines and derivatives / Monoalkyl phosphates / Hydropyrimidines / Imidolactams
show 13 more
Substituents
1,2-diol / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative
show 31 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
phosphocholines, nucleotide-(amino alcohol)s (CHEBI:16436)
Affected organisms
Not Available

Chemical Identifiers

UNII
536BQ2JVC7
CAS number
987-78-0
InChI Key
RZZPDXZPRHQOCG-OJAKKHQRSA-N
InChI
InChI=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
IUPAC Name
{2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium
SMILES
C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O

References

General References
  1. AIFA Product Information: Difosfocin (citicoline) solution for injection [Link]
  2. INVIMA Product Information: Complegel NF (citicoline) coated tablets [Link]
Human Metabolome Database
HMDB0001413
KEGG Drug
D00057
KEGG Compound
C00307
PubChem Substance
347911290
ChemSpider
13207
RxNav
997602
ChEBI
16436
ChEMBL
CHEMBL1231700
PDBe Ligand
CDC
Wikipedia
Citicoline
PDB Entries
1jyl / 3hl4 / 4bet / 4mvc / 4mvd / 4zcs

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedSupportive CareBipolar Disorder (BD) / Dependence, Cocaine1
4CompletedTreatmentAlcohol Dependency1
4CompletedTreatmentCerebral Infarctions1
4CompletedTreatmentGlaucoma / Neural Conduction / Optic Nerve / Optic Neuropathy, Ischemic / Visual pathway disorders1
4CompletedTreatmentNon-Arteritic Anterior Ischemic Optic Neuropathy1
4RecruitingTreatmentAlcohol Use Disorders (AUD) / Bipolar Disorder (BD)1
4WithdrawnOtherDelirium1
3CompletedDiagnosticCerebrovascular Accident1
3CompletedTreatmentCocaine Abuse / Dependence, Cocaine / Hypomania / Mania1
3CompletedTreatmentMethamphetamine Dependence1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
InjectionIntramuscular; Intravenous1000 mg/4ml
InjectionIntramuscular; Intravenous500 mg/4ml
Injection, solutionIntramuscular; Intravenous1045 MG
Injection, solutionIntramuscular; Intravenous522.5 MG
InjectionIntramuscular; Intravenous125 MG/ML
Injection, solution1000 MG/4ML
Injection, solutionIntramuscular; Intravenous0.1 g/2ml
Injection, solutionIntramuscular; Intravenous1 g/4ml
Injection, solutionIntramuscular; Intravenous250 mg/2ml
Injection, solutionIntramuscular; Intravenous500 mg/4ml
Injection, solutionIntramuscular; Intravenous; Intravenous drip100 mg
Injection, solutionIntramuscular; Intravenous; Intravenous drip1000 mg
Injection, solutionIntramuscular
SolutionOral1 g
InjectionIntramuscular; Intravenous125 MG
TabletOral522.6 mg
Injection, solutionIntramuscular; Intravenous1000 mg
InjectionIntramuscular; Intravenous100 mg
InjectionIntramuscular; Intravenous1000 mg
InjectionIntramuscular; Intravenous250 mg
InjectionIntramuscular; Intravenous500 mg
Injection, solution
InjectionIntramuscular; Intravenous
Tablet, coatedOral500 mg
Injection, solutionIntramuscular; Intravenous500 mg
Injection, solutionIntramuscular; Intravenous125 mg/ml
SolutionOral1000 MG
SolutionOral1000 mg/4ml
Injection, solution500 mg/4ml
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.99 mg/mLALOGPS
logP-1.4ALOGPS
logP-7.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area213.5 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity113.58 m3·mol-1ChemAxon
Polarizability42.54 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9964
Blood Brain Barrier-0.626
Caco-2 permeable-0.6489
P-glycoprotein substrateSubstrate0.6427
P-glycoprotein inhibitor INon-inhibitor0.9504
P-glycoprotein inhibitor IINon-inhibitor0.9873
Renal organic cation transporterNon-inhibitor0.9328
CYP450 2C9 substrateNon-substrate0.7797
CYP450 2D6 substrateNon-substrate0.8109
CYP450 3A4 substrateSubstrate0.6171
CYP450 1A2 substrateNon-inhibitor0.8289
CYP450 2C9 inhibitorNon-inhibitor0.8439
CYP450 2D6 inhibitorNon-inhibitor0.8274
CYP450 2C19 inhibitorNon-inhibitor0.8009
CYP450 3A4 inhibitorNon-inhibitor0.8877
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9675
Ames testNon AMES toxic0.6538
CarcinogenicityNon-carcinogens0.8806
BiodegradationReady biodegradable0.7564
Rat acute toxicity1.6863 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9031
hERG inhibition (predictor II)Non-inhibitor0.6674
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0006-0001900000-a9f38ff6b185b45f04b3
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-03e9-0590000000-b021677d064d65810ee0
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-001i-0900000000-7570bbb10dd9fa288442
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-000i-0000900000-8b411373962b073b4d22
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-000i-0001900000-6e7cc437ad79eb13c032
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-01qi-1932200000-9c3803cefdd9c6285a7c
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-004i-6505900000-3d534aab6e40915c3642
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-004i-6505900000-fc13e5ad403e7faf8218
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-6505900000-3d534aab6e40915c3642
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-004i-6505900000-fc13e5ad403e7faf8218
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0000900000-8b411373962b073b4d22
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0001900000-6e7cc437ad79eb13c032
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01qi-1932200000-4a7ae92c6e127d2ce453
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets2
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Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Not Available
Gene Name
licC
Uniprot ID
A0A0H2UQB5
Uniprot Name
LicC protein
Molecular Weight
26903.28 Da

Drug created on October 20, 2016 21:29 / Updated on May 21, 2021 10:22