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
Structure for Choline alfoscerate (DB04660)
- 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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- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism UGanglioside GM2 activator Not Available Humans - 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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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
- Alcohols
- Biological Products
- Carbohydrates
- Complex Mixtures
- Glycerophosphates
- Glycerophospholipids
- Lecithins
- Lipids
- Membrane Lipids
- Nervous System
- Parasympathomimetics
- Pharmaceutical Preparations
- Phosphatidic Acids
- Phosphatidylcholines
- Phospholipids
- Plant Extracts
- Plant Preparations
- Sugar Alcohols
- Sugar Phosphates
- Triose Sugar Alcohols
- 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
- 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]
- External Links
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Cerebrovascular Accident / Cognitive Impairment (CI) 1 4 Unknown Status Treatment Alzheimer's Disease (AD) 1 3 Completed Treatment Type 2 Diabetes Mellitus 1 2 Completed Treatment Vascular Cognitive Impairment 1 1 Completed Treatment Healthy, Male 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 400 MG Capsule Oral 600 MG Injection, solution Intramuscular; Intravenous Solution Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 8.96 mg/mL ALOGPS logP -2.6 ALOGPS logP -5.7 ChemAxon logS -1.5 ALOGPS pKa (Strongest Acidic) 1.86 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 99.05 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 68.68 m3·mol-1 ChemAxon Polarizability 24.74 Å3 ChemAxon Number of Rings 0 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 - 0.9988 Blood Brain Barrier + 0.567 Caco-2 permeable - 0.5577 P-glycoprotein substrate Substrate 0.6093 P-glycoprotein inhibitor I Non-inhibitor 0.8609 P-glycoprotein inhibitor II Non-inhibitor 0.9342 Renal organic cation transporter Non-inhibitor 0.8826 CYP450 2C9 substrate Non-substrate 0.8492 CYP450 2D6 substrate Non-substrate 0.7639 CYP450 3A4 substrate Substrate 0.517 CYP450 1A2 substrate Non-inhibitor 0.8694 CYP450 2C9 inhibitor Non-inhibitor 0.8303 CYP450 2D6 inhibitor Non-inhibitor 0.9125 CYP450 2C19 inhibitor Non-inhibitor 0.8033 CYP450 3A4 inhibitor Non-inhibitor 0.8768 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9893 Ames test Non AMES toxic 0.7255 Carcinogenicity Non-carcinogens 0.6032 Biodegradation Ready biodegradable 0.7601 Rat acute toxicity 2.5370 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5625 hERG inhibition (predictor II) Non-inhibitor 0.7148
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
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 on September 11, 2007 17:49 / Updated on June 12, 2021 10:53