Citicoline

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

Identification

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Name
Citicoline
Accession Number
DB12153  (EXPT00867, DB04290)
Type
Small Molecule
Groups
Approved, Experimental
Description

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

Structure
Thumb
Synonyms
  • CDP-choline
  • CDP-colina
  • citicolina
  • citidin difosfato de colina
  • Cytidine 5'-(choline diphosphate)
  • Cytidine 5'-(cholinyl pyrophosphate)
  • Cytidine 5'-diphosphocholine
  • Cytidine 5'-diphosphoric choline
  • Cytidine-5'-diphosphocholine
Product Ingredients
IngredientUNIICASInChI Key
Citicoline sodium7XQ5AKD9YD33818-15-4YWAFNFGRBBBSPD-OCMLZEEQSA-M
Categories
UNII
536BQ2JVC7
CAS number
987-78-0
Weight
Average: 488.324
Monoisotopic: 488.107330718
Chemical Formula
C14H26N4O11P2
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001413
KEGG Drug
D00057
KEGG Compound
C00307
PubChem Substance
347911290
ChemSpider
13207
ChEBI
16436
ChEMBL
CHEMBL1231700
HET
CDC
Wikipedia
Citicoline
ATC Codes
N06BX06 — Citicoline
PDB Entries
1jyl / 3hl4 / 4bet / 4mvc / 4mvd / 4zcs

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentNeurocognitive Improvement1
1WithdrawnTreatmentStroke, Ischemic1
2CompletedTreatmentBrain Injury1
2CompletedTreatmentMarijuana Abuse1
2CompletedTreatmentSchizophrenic Disorders1
2RecruitingTreatmentSubstance Use Disorder (SUD)1
2WithdrawnTreatmentTraumatic Brain Injury (TBI)1
3CompletedDiagnosticStrokes1
3CompletedTreatmentCocaine Abuse / Dependence, Cocaine / Hypomania / Mania1
3CompletedTreatmentMethamphetamine Dependence1
3RecruitingTreatmentHypoxic-Ischaemic Encephalopathy1
3RecruitingTreatmentNeonatal hypoxia1
3RecruitingTreatmentPre-Term1
3TerminatedTreatmentCerebral Infarctions / Stroke, Acute1
3TerminatedTreatmentTraumatic Brain Injury (TBI)1
4CompletedSupportive CareBipolar Disorder (BD) / Dependence, Cocaine1
4CompletedTreatmentAlcohol Dependence1
4CompletedTreatmentCerebral Infarctions1
4CompletedTreatmentGlaucoma / Neural Conduction / Optic Nerve / Optic Neuropathy, Ischemic / Visual Pathways1
4RecruitingTreatmentAlcohol Use Disorder (AUD) / Bipolar Disorder (BD)1
4WithdrawnOtherDelirium1
Not AvailableCompletedTreatmentAmphetamine Abuse / Amphetamine Dependence / Bipolar Disorder (BD) / Major Depressive Disorder (MDD)1
Not AvailableWithdrawnTreatmentSubstance Abuse / Substance Dependence / Traumatic Brain Injury (TBI)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
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

Taxonomy

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
Pyrimidine ribonucleoside diphosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / Phosphocholine / Monosaccharide phosphate / Organic pyrophosphate / Pentose monosaccharide / Aminopyrimidine
show 31 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
phosphocholines, nucleotide-(amino alcohol)s (CHEBI:16436)

Targets

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 15:29 / Updated on June 04, 2019 07:32