Citicoline
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Also known as Cdp-cholineCiticolinaCytidine 5'-diphosphate cholineCytidine-5'-diphosphocholineIP 302IP-302NicholinNSC-122002SID90340858
Summary
Citicoline (CHEMBL1231700) is a phase-3 clinical-stage small-molecule psychotropic drug (ATC N06BX06); indicated across 11 conditions including stroke disorder and methamphetamine dependence.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Small molecule
- ATC class: N06BX06
- Indications: 11 conditions
- Clinical trials: 42
- Chemistry: 488.32 Da · C14H26N4O11P2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1231700 |
| Name | Citicoline |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 11583971 |
| ChEBI | CHEBI:16436 |
| ATC | N06BX06 |
| Molecular formula | C14H26N4O11P2 |
| Molecular weight | 488.32 |
| InChIKey | RZZPDXZPRHQOCG-OJAKKHQRSA-N |
SMILES: C[N+](C)(C)CCOP(=O)(O)OP(=O)([O-])OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)N)O)O
IUPAC name: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl [hydroxy-[2-(trimethylazaniumyl)ethoxy]phosphoryl] phosphate
ChEBI definition: A member of the class of phosphocholines that is the choline ester of CDP. It is an intermediate obtained in the biosynthetic pathway of structural phospholipids in cell membranes.
Pharmacological roles (ChEBI): psychotropic drug, neuroprotective agent.
Other ChEBI roles (chemical / environmental): human metabolite, Saccharomyces cerevisiae metabolite, mouse metabolite.
Also known as: Cdp-choline, Citicolina, Citicoline, Cytidine 5’-diphosphate choline, Cytidine-5’-diphosphocholine, IP 302, IP-302, Nicholin, NSC-122002, SID90340858, CITICOLINE, citicoline
Parent form; salt/anhydrous children: CHEMBL1256994
Patent coverage: 960 distinct patent families (2,679 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 2,176 (81%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
No target linkage available.
Bioactivity
No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
11 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| stroke disorder | 3 | MONDO:0005098 | EFO:0000712 |
| methamphetamine dependence | 3 | MONDO:0005419 | EFO:0004701 |
| attention deficit-hyperactivity disorder | 3 | MONDO:0007743 | EFO:0003888 |
| cerebral infarction | 3 | MONDO:0002679 | MONDO:0002679 |
| brain ischemia | 3 | MONDO:0005299 | MONDO:0005299 |
| brain injury | 3 | MONDO:0043510 | MONDO:0043510 |
| open-angle glaucoma | 3 | MONDO:0005338 | EFO:0004190 |
| cannabis dependence | 2 | MONDO:0005689 | EFO:0007191 |
| alcohol abuse | 2 | MONDO:0002046 | MONDO:0007079 |
| severe acute respiratory syndrome | 1 | MONDO:0005091 | MONDO:0100096 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 42.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 15 |
| PHASE3 | 11 |
| PHASE4 | 6 |
| PHASE2 | 6 |
| PHASE2/PHASE3 | 1 |
| PHASE1/PHASE2 | 1 |
| EARLY_PHASE1 | 1 |
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00404729 | PHASE4 | COMPLETED | Neural Conduction Along the Visual Pathways After Oral Treatment With Citicoline in Patients With Optic Nerve Diseases |
| NCT00619723 | PHASE4 | COMPLETED | Citicoline for Bipolar 1 Disorder and Cocaine Dependence |
| NCT02074735 | PHASE4 | COMPLETED | Citicoline for Alcohol Dependence |
| NCT02248233 | PHASE4 | COMPLETED | Nimodipine for Treating Acute Massive Cerebral Infarction |
| NCT02582905 | PHASE4 | COMPLETED | Clinical Medication Development for Bipolar Disorder and Alcohol Use Disorders |
| NCT02840591 | PHASE4 | WITHDRAWN | Ramelteon and Citicoline for Delirium |
| NCT03949049 | PHASE3 | RECRUITING | Citicoline as Neuroprotector in Neonates Exposed to Hypoxia |
| NCT03966170 | PHASE3 | RECRUITING | Citicoline as Neuroprotector in Preterm |
| NCT00223236 | PHASE3 | COMPLETED | Trial of Citicoline Therapy in Patients With Mania or Hypomania and Cocaine Abuse/Dependence |
| NCT00331890 | PHASE3 | TERMINATED | ICTUS Study: International Citicoline Trial on Acute Stroke |
| NCT00545662 | PHASE3 | TERMINATED | Study of Citicoline for the Treatment of Traumatic Brain Injury (COBRIT) |
| NCT00950352 | PHASE3 | COMPLETED | Citicoline Treatment of Methamphetamine Dependence |
| NCT01007539 | PHASE3 | COMPLETED | Efficacy and Safety of CDP-choline in Patients With Methamphetamine Dependence |
| NCT01388738 | PHASE3 | COMPLETED | Navigation Brain Stimulation for Evaluation of the Neuroprotective Drug Efficiency in Patients After Ischemic Stroke. |
| NCT03181646 | PHASE3 | UNKNOWN | Role of Citicoline in Treatment of Newborns With Hypoxic Ischemic Encephalopathy |
| NCT04802785 | PHASE2/PHASE3 | UNKNOWN | The Impact of Air Travel on Passenger Cognitive Functions |
| NCT05154903 | PHASE3 | UNKNOWN | Citicoline in Ischemic Stroke |
| NCT06210646 | PHASE3 | COMPLETED | Citicoline in Ischemic Stroke, a Randomized Trial |
| NCT05881135 | PHASE1/PHASE2 | ACTIVE_NOT_RECRUITING | Supplemental Citicoline Administration to Reduce Lung Injury Efficacy Trial (SCARLET) |
| NCT00158249 | PHASE2 | COMPLETED | Effects of Citicoline on Brain Function and Behavior in Marijuana-Dependent Individuals |
| NCT00509067 | PHASE2 | COMPLETED | Use of Galantamine and CDP-choline (Citicoline) to Treat Adults With Schizophrenia |
| NCT00727246 | PHASE2 | COMPLETED | CDP-Choline and Working Memory After TBI: A Neuroimaging Study |
| NCT01591759 | PHASE2 | WITHDRAWN | A Pilot Trial of Citicoline in Individuals With Mild Traumatic Brain Injury (mTBI) |
| NCT02088983 | PHASE2 | UNKNOWN | Effects of CDP-Choline on Gating and Cognitive Deficits in First Episode Schizophrenia |
| NCT02630069 | PHASE2 | UNKNOWN | CDP-choline Treatment in ATS Users |
| NCT02823106 | PHASE1 | WITHDRAWN | Superselective Citicoline and Verapamil for Ischemic Neuroprotection and Greater Effective Response |
| NCT01582113 | EARLY_PHASE1 | COMPLETED | Cognizin Citicoline Dosing in a Healthy Adolescent Male Population |
| NCT05315206 | Not specified | ACTIVE_NOT_RECRUITING | Multimodal Morpho-functional Study in Glaucoma Patients-Citicoline Oral Solution |
| NCT07089238 | Not specified | RECRUITING | Evaluate the Effects of Citicoline on Mood in Healthy Adults |
| NCT00377299 | Not specified | COMPLETED | A Pilot Study of Citicoline add-on Therapy in Patients With Bipolar Disorder or Major Depressive Disorder and Amphetamine Abuse or Dependence |
| NCT01338389 | Not specified | COMPLETED | Influence of Oral Treatment With Citicoline for the Prevention of Radiation Optic Neuropathy in Patients Treated for Uveal Melanomas With Proton Beam Therapy |
| NCT01515917 | Not specified | WITHDRAWN | Citicoline and Omega-3 Fatty Acid Effects in Veterans With Traumatic Brain Injury (TBI) |
| NCT02705066 | Not specified | COMPLETED | Citicoline Effects on Cortical Membrane Structure and Function |
| NCT03369925 | Not specified | COMPLETED | Cognitive Effects of Citicoline in Men and Women With Age-Associated Memory Impairment |
| NCT03444662 | Not specified | COMPLETED | The Combination Effect of Citicoline and Omega-3 |
| NCT03758118 | Not specified | COMPLETED | Citicoline in Non-Arteritic Ischemic Optic Neuropathy |
| NCT04003090 | Not specified | COMPLETED | Citicoline Concentration in Human Vitreous |
| NCT04967157 | Not specified | COMPLETED | Cognitive Effects of Citicoline on Attention in Healthy Mean and Women |
| NCT05200208 | Not specified | COMPLETED | Improving Sleep and Cognition in Alzheimer’s Disease |
| NCT05527106 | Not specified | COMPLETED | Evaluation of the Effect of Citicoline and Docosahexaenoic Acid (DHA) on the Visual Function of Patients With Glaucoma |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No PharmGKB pharmacogenomic data curated for this drug.
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).