Citicoline
Star12
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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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
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Degenerative brain disorder •••••••••••• Management of Parkinsonian syndromes •••••••••••• •••••••••• •••••••••• •••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ULicC protein Not Available Streptococcus 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Citicoline sodium 7XQ5AKD9YD 33818-15-4 YWAFNFGRBBBSPD-OCMLZEEQSA-M
Categories
- ATC Codes
- N06BX06 — Citicoline
- Drug Categories
- Amines
- Central Nervous System Agents
- Cytidine Diphosphate
- Cytosine Nucleotides
- Nervous System
- Nootropic Agents
- Nucleic Acids, Nucleotides, and Nucleosides
- Nucleotides
- Onium Compounds
- Psychoanaleptics
- Psychostimulants, Agents Used for ADHD and Nootropics
- Pyrimidine Nucleotides
- Pyrimidines
- Quaternary Ammonium Compounds
- Ribonucleotides
- Trimethyl Ammonium Compounds
- 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
- External Links
- Human Metabolome Database
- HMDB0001413
- KEGG Drug
- D00057
- KEGG Compound
- C00307
- PubChem Substance
- 347911290
- ChemSpider
- 13207
- 997602
- ChEBI
- 16436
- ChEMBL
- CHEMBL1231700
- PDBe Ligand
- CDC
- Wikipedia
- Citicoline
- PDB Entries
- 1jyl / 3hl4 / 4bet / 4mvc / 4mvd / 4zcs / 8erp / 8gyw
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Treatment Amphetamine Abuse / Amphetamine Dependence / Bipolar Disorder (BD) / Major Depressive Disorder (MDD) 1 somestatus stop reason just information to hide Not Available Completed Treatment Cognitive Benefits 1 somestatus stop reason just information to hide Not Available Completed Treatment Neurodegenerative Disorders 1 somestatus stop reason just information to hide Not Available Recruiting Treatment Analgesia / Cesarean Sections / Postoperative pain 1 somestatus stop reason just information to hide Not Available Withdrawn Treatment Substance Abuse / Substance Dependence / Traumatic Brain Injury (TBI) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection Intramuscular; Intravenous 1000 mg/4ml Injection Intramuscular; Intravenous 500 mg/4ml Injection, solution Intramuscular; Intravenous 1045 MG Injection, solution Intramuscular; Intravenous 522.5 MG Tablet Oral 522.500 mg Injection Intramuscular; Intravenous 130.63 mg Injection, solution 1000 MG/4ML Injection, solution Intramuscular; Intravenous 0.1 g/2ml Injection, solution Intramuscular; Intravenous 1 g/4ml Injection, solution Intramuscular; Intravenous 250 mg/2ml Injection, solution Intramuscular; Intravenous 500 mg/4ml Injection, solution Intramuscular; Intravenous; Intravenous drip 100 mg Injection, solution Intramuscular; Intravenous; Intravenous drip 1000 mg Injection, solution Intramuscular Injection Intramuscular; Intravenous 125 mg/ml Solution Oral 1 g Injection Intramuscular; Intravenous 125 mg Tablet Oral 522.6 mg Injection, solution Intramuscular; Intravenous 1000 mg Tablet Oral 522.506 mg Injection Intramuscular; Intravenous 100 mg Injection Intramuscular; Intravenous 1000 mg Injection Intramuscular; Intravenous 250 mg Injection Intramuscular; Intravenous 500 mg Injection Intramuscular; Intravenous 522.537 mg Injection Intramuscular; Intravenous Injection, solution Injection Intramuscular; Intravenous 250 MG/2ML Solution Parenteral 1045.020 mg Injection, solution Intramuscular; Intravenous 1000 mg/4ml Solution Oral 1000.000 mg Solution Intravenous 1000.000 mg Tablet Oral 500 mg Tablet, coated Oral 500 mg Injection, solution Intramuscular; Intravenous 500 mg Tablet, coated Oral 50000000 mg Injection, solution Intramuscular; Intravenous 125 mg/ml Solution Oral 1000 MG Solution Intravenous 523.577 mg Tablet Oral 500.000 mg Solution Oral 1000 mg/4ml Injection, solution 500 mg/4ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 7.99 mg/mL ALOGPS logP -1.4 ALOGPS logP -7.1 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 1.84 Chemaxon pKa (Strongest Basic) -2.6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 213.5 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 113.58 m3·mol-1 Chemaxon Polarizability 42.54 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9964 Blood Brain Barrier - 0.626 Caco-2 permeable - 0.6489 P-glycoprotein substrate Substrate 0.6427 P-glycoprotein inhibitor I Non-inhibitor 0.9504 P-glycoprotein inhibitor II Non-inhibitor 0.9873 Renal organic cation transporter Non-inhibitor 0.9328 CYP450 2C9 substrate Non-substrate 0.7797 CYP450 2D6 substrate Non-substrate 0.8109 CYP450 3A4 substrate Substrate 0.6171 CYP450 1A2 substrate Non-inhibitor 0.8289 CYP450 2C9 inhibitor Non-inhibitor 0.8439 CYP450 2D6 inhibitor Non-inhibitor 0.8274 CYP450 2C19 inhibitor Non-inhibitor 0.8009 CYP450 3A4 inhibitor Non-inhibitor 0.8877 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9675 Ames test Non AMES toxic 0.6538 Carcinogenicity Non-carcinogens 0.8806 Biodegradation Ready biodegradable 0.7564 Rat acute toxicity 1.6863 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9031 hERG inhibition (predictor II) Non-inhibitor 0.6674
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 235.1178185 predictedDarkChem Lite v0.1.0 [M-H]- 228.3908185 predictedDarkChem Lite v0.1.0 [M-H]- 186.6222 predictedDeepCCS 1.0 (2019) [M+H]+ 236.3929185 predictedDarkChem Lite v0.1.0 [M+H]+ 229.6900185 predictedDarkChem Lite v0.1.0 [M+H]+ 188.5176 predictedDeepCCS 1.0 (2019) [M+Na]+ 235.3875185 predictedDarkChem Lite v0.1.0 [M+Na]+ 229.0222185 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.3821 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsLicC protein
- Kind
- Protein
- Organism
- Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- metal ion binding
- Gene Name
- licC
- Uniprot ID
- A0A0H2UQB5
- Uniprot Name
- LicC protein
- Molecular Weight
- 26903.28 Da
Drug created at October 20, 2016 21:29 / Updated at May 21, 2021 10:22