CHOLINE ALFOSCERATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C8H20NO6P
Molecular Weight	257.2213
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(C)CCOP([O-])(=O)OC[C@H](O)CO

InChI

InChIKey=SUHOQUVVVLNYQR-MRVPVSSYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C8H20NO6P
Molecular Weight	257.2213
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	1 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://examine.com/supplements/alpha-gpc/ | https://www.rxlist.com/alpha-gpc/supplements.htm | https://www.ncbi.nlm.nih.gov/pubmed/24156263

Choline alfoscerate (alpha-Glycerylphosphorylcholine or Alpha-GPC) is a nootropic choline-containing phospholipid. Choline alphoscerate increases the release of acetylcholine in rat hippocampus, facilitates learning and memory in experimental animals, improves brain transduction mechanisms and decreases age-dependent structural changes occurring in rat brain areas involved in learning and memory. The compound exerts neuroprotective effects in models of altered cholinergic neurotransmission and of brain vascular injury. In clinical studies choline alphoscerate improved memory and attention impairment, as well as affective and somatic symptoms in dementia disorders. In Europe alpha-GPC is a prescription medication for the treatment of Alzheimer's disease. It is available in two forms; one is taken by mouth, and the other is given as a shot. In the United States alpha-GPC is only available as a dietary supplement, mostly in products promoted to improve memory. Other uses for alpha-GPC include treatment of various kinds of dementia, stroke, and "mini-stroke" (transient ischemic attack, TIA). Alpha-GPC is also used for improving memory, thinking skills, and learning.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
neurological system process 6 Target ID: GO:0050877 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24156263 \| https://examine.com/supplements/alpha-gpc/ \| https://www.rxlist.com/alpha-gpc/supplements.htm	Modulator 846
acetylcholine secretion 4 Target ID: GO:0061526 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24156263	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cognitive impairment 15 Sources: http://adisinsight.springer.com/drugs/800006542	Primary		Approved 8583	Gliatilin Approved Use Unknown
Cerebrovascular insufficiency 15 Sources: http://adisinsight.springer.com/drugs/800006542	Primary		Approved 8583	Gliatilin Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.38 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31040642/	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:		CHOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
3.31 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31040642/	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:		CHOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.25 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31040642/	1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered:		CHOLINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
400 mg 3 times / day multiple, oral Studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12637119/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12637119/	Sources: https://pubmed.ncbi.nlm.nih.gov/12637119/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2E1 1060 CYP2A6 879 CYP2C19 2057 BCRP 910 P-gp 1741

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1Njc0NjMifX0=	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1Njc0NjMifX0=	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1Njc0NjMifX0=	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1Njc0NjMifX0=	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU2NzQ2MyJ9fQ==	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1Njc0NjMifX0=	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU2NzQ2MyJ9fQ==	no [IC50 >10 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/657272#section=Biological-Test-Results Page: 44.0	no
MRP1 232	activator 342 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/657272#section=Biological-Test-Results Page: 29.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/657272#section=Biological-Test-Results Page: 46.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU2NzQ2MyJ9fQ==

PubMed

Title	Date	PubMed
Correlation of antiphospholipid antibody recognition with the structure of synthetic oxidized phospholipids. Importance of Schiff base formation and aldol condensation.	2002-03-01	11744722
Molecular mechanisms mediating the effects of L-alpha-glycerylphosphorylcholine, a new cognition-enhancing drug, on behavioral and biochemical parameters in young and aged rats.	1992-09	1409797
Effect of a new cognition enhancer, alpha-glycerylphosphorylcholine, on scopolamine-induced amnesia and brain acetylcholine.	1991-08	1662399
Effect of L-alpha-glyceryl-phosphorylcholine on amnesia caused by scopolamine.	1991-03	2071257

Patents

Sample Use Guides

In Vivo Use Guide

300-1200 mg daily

Route of Administration: Other

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:24:03 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:03 GMT 2025`
Record UNII	60M22SGW66
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GLYCEROPHOSPHOCHOLINE

Preferred Name

English

CHOLINE ALFOSCERATE

Official Name

English

CHOLINE ALFOSCERATE [MART.]

Common Name

English

CHOLINE ALFOSCERATE [MI]

Common Name

English

choline alfoscerate [INN]

Common Name

English

CHOLINE HYDROXIDE, (R)-2,3-DIHYDROXYPROPYL HYDROGEN PHOSPHATE, INNER SALT

Common Name

English

L-ALPHA-GLYCERYLPHOSPHORYLCHOLINE [USP-RS]

Common Name

English

L-.ALPHA.-GLYCERYLPHOSPHORYLCHOLINE

Brand Name

English

Choline alfoscerate [WHO-DD]

Common Name

English

ALPHA-GLYCERYLPHOSPHORYLCHOLINE

Common Name

English

ETHANAMINIUM, 2-((((2R)-2,3-DIHYDROXYPROPOXXY)HYDROXYPHOSPHINYL)OXY)-N,N,N-TRIMETHYL-, INNER SALT

Common Name

English

CHOLINE ALPHOSCERATE

Common Name

English

GLIATILIN

Brand Name

English

Classification Tree Code System Code

WHO-ATC

N07AX02