Choline alfoscerate

Identification

Summary

Choline alfoscerate is a natural choline that is used to manage declining cognitive function associated with neurodegenerative and vascular diseases.

Generic Name
Choline alfoscerate
DrugBank Accession Number
DB04660
Background

A component of phosphatidylcholines (lecithins), in which the two hydroxy groups of glycerol are esterified with fatty acids. (From Stedman, 26th ed) It counteracts the effects of urea on enzymes and other macromolecules. [PubChem]

Type
Small Molecule
Groups
Experimental, Investigational
Structure
Weight
Average: 257.223
Monoisotopic: 257.102824366
Chemical Formula
C8H20NO6P
Synonyms
  • (2R)-2,3-dihydroxypropyl 2-(trimethylammonio)ethyl phosphate
  • alpha-Glycerophosphorylcholine
  • Choline alfoscerate
  • Choline alphoscerate
  • Choline glycerophosphate
  • Cholini glycerophosphas
  • Glicerofosfato de colina
  • Glycerol phosphorylcholine
  • Glycerol-3-phosphatidylcholine
  • glycerol-3-phosphocholine
  • Glycerophosphate de choline
  • Glycerophosphocholine
  • Glycerophosphorylcholine
  • GPCho
  • L-alpha-Glycerophosphocholine
  • L-alpha-Glycerophosphorylcholine
  • sn-3-GPC
  • sn-Glycero-3-phosphocholine

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofAffective disorders••••••••••••••••••••••••••• ••••••••
Management ofAffective disorders••••••••••••••••••••••••••• ••••••••
Management ofCognitive disorders•••••••••••••••••••••• ••••••••
Management ofCognitive disorders•••••••••••••••••••••• ••••••••
Management ofCognitive disorders••••••••••••••••••••••••••• ••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGanglioside GM2 activatorNot AvailableHumans
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
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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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Categories

ATC Codes
N07AX02 — Choline alfoscerate
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as glycerophosphocholines. These are lipids containing a glycerol moiety carrying a phosphocholine at the 3-position.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Glycerophospholipids
Sub Class
Glycerophosphocholines
Direct Parent
Glycerophosphocholines
Alternative Parents
Phosphocholines / Dialkyl phosphates / Tetraalkylammonium salts / Secondary alcohols / 1,2-diols / Primary alcohols / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
1,2-diol / Alcohol / Aliphatic acyclic compound / Alkyl phosphate / Amine / Dialkyl phosphate / Glycero-3-phosphocholine / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
phosphocholines, sn-glycerol 3-phosphates (CHEBI:16870)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
60M22SGW66
CAS number
28319-77-9
InChI Key
SUHOQUVVVLNYQR-MRVPVSSYSA-N
InChI
InChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m1/s1
IUPAC Name
(2-{[(2R)-2,3-dihydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
SMILES
[H][C@@](O)(CO)COP([O-])(=O)OCC[N+](C)(C)C

References

Synthesis Reference

Carlo Scolastico, Giovanni Tronconi, "Diacyl derivatives of glycerylphosphorylcholine, their preparation, and antihyperlipidemic compositions." U.S. Patent US4699901, issued October 13, 1987.

US4699901
General References
  1. Ferraro L, Tanganelli S, Marani L, Bianchi C, Beani L, Siniscalchi A: Evidence for an in vivo and in vitro modulation of endogenous cortical GABA release by alpha-glycerylphosphorylcholine. Neurochem Res. 1996 May;21(5):547-52. [Article]
KEGG Drug
D07349
KEGG Compound
C00670
PubChem Compound
657272
PubChem Substance
46508680
ChemSpider
571409
RxNav
4918
ChEBI
16870
ChEMBL
CHEMBL1567463
PDBe Ligand
CH5
Wikipedia
Alpha-GPC

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCognitive Impairment (CI) / Stroke1
4Not Yet RecruitingTreatmentMild Cognitive Impairment (MCI)1
4Not Yet RecruitingTreatmentVascular Cognitive Impairment1
4RecruitingTreatmentAlzheimer's Disease (AD)1
4Unknown StatusTreatmentAlzheimer's Disease (AD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral400 MG
CapsuleOral600 MG
Injection, solutionIntramuscular; Intravenous
SolutionOral
Injection, solutionIntramuscular; Intravenous1000 mg/4ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility8.96 mg/mLALOGPS
logP-2.6ALOGPS
logP-5.7Chemaxon
logS-1.5ALOGPS
pKa (Strongest Acidic)1.86Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.05 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity68.68 m3·mol-1Chemaxon
Polarizability24.74 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9988
Blood Brain Barrier+0.567
Caco-2 permeable-0.5577
P-glycoprotein substrateSubstrate0.6093
P-glycoprotein inhibitor INon-inhibitor0.8609
P-glycoprotein inhibitor IINon-inhibitor0.9342
Renal organic cation transporterNon-inhibitor0.8826
CYP450 2C9 substrateNon-substrate0.8492
CYP450 2D6 substrateNon-substrate0.7639
CYP450 3A4 substrateSubstrate0.517
CYP450 1A2 substrateNon-inhibitor0.8694
CYP450 2C9 inhibitorNon-inhibitor0.8303
CYP450 2D6 inhibitorNon-inhibitor0.9125
CYP450 2C19 inhibitorNon-inhibitor0.8033
CYP450 3A4 inhibitorNon-inhibitor0.8768
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9893
Ames testNon AMES toxic0.7255
CarcinogenicityNon-carcinogens0.6032
BiodegradationReady biodegradable0.7601
Rat acute toxicity2.5370 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5625
hERG inhibition (predictor II)Non-inhibitor0.7148
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-MSsplash10-001j-7910000000-79a0f6ec434740d09410
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-162.40731
predicted
DarkChem Lite v0.1.0
[M-H]-149.81558
predicted
DeepCCS 1.0 (2019)
[M+H]+164.46031
predicted
DarkChem Lite v0.1.0
[M+H]+152.03165
predicted
DeepCCS 1.0 (2019)
[M+Na]+161.46131
predicted
DarkChem Lite v0.1.0
[M+Na]+157.94417
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase activator activity
Specific Function
The large binding pocket can accommodate several single chain phospholipids and fatty acids, GM2A also exhibits some calcium-independent phospholipase activity (By similarity). Binds gangliosides a...
Gene Name
GM2A
Uniprot ID
P17900
Uniprot Name
Ganglioside GM2 activator
Molecular Weight
20838.1 Da

Drug created at September 11, 2007 17:49 / Updated at June 12, 2021 10:53