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Details

Stereochemistry ACHIRAL
Molecular Formula C5H14NO
Molecular Weight 104.1708
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of CHOLINE

SMILES

C[N+](C)(C)CCO

InChI

InChIKey=OEYIOHPDSNJKLS-UHFFFAOYSA-N
InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1

HIDE SMILES / InChI

Molecular Formula C5H13NO
Molecular Weight 103.1628
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT02669641 | https://clinicaltrials.gov/ct2/show/NCT01098383 | https://clinicaltrials.gov/ct2/show/NCT00720343 | https://www.ncbi.nlm.nih.gov/pubmed/15213044 | https://www.ncbi.nlm.nih.gov/pubmed/28152052

CHOLINE is a basic constituent of lecithin that is found in many plants and animal organs. Choline was officially recognized as an essential nutrient by the Institute of Medicine in 1998.1 Its role in the body is complex. It is needed for neurotransmitter synthesis (acetylcholine), cell-membrane signaling (phospholipids), lipid transport (lipoproteins), and methyl-group metabolism (homocysteine reduction). It is the major dietary source of methyl groups via the synthesis of S-adenosylmethionine (AdoMet). At least 50 AdoMet-dependent reactions have been identified in mammals, and it is likely that the number is much higher. Choline is required to make the phospholipids phosphatidylcholine, lysophosphatidylcholine, choline plasmalogen, and sphingomyelin—essential components for all membranes. It plays important roles in brain and memory development in the fetus and appears to decrease the risk of the development of neural tube defects. The importance of choline in the diet extends into adulthood and old age. In a study of healthy adult subjects deprived of dietary choline, 77% of the men and 80% of the postmenopausal women developed signs of subclinical organ dysfunction (fatty liver or muscle damage). Less than half of premenopausal women developed such signs. Ten percent of the subjects studied developed fatty liver, muscle damage, or both when they consumed the Adequate Intake (AI) of choline. The damage was reversed when they consumed a high-choline diet. Plasma choline concentration has been found to vary in response to diet, decreasing approximately 30 percent in humans fed a choline-deficient diet for 3 weeks. Based on estimated dietary intakes and studies reporting liver damage with lower choline intakes, the Institute of Medicine, Food and Nutrition Board set the AI for choline at 425 milligrams/per day for women aged 19 and older, and 550 milligrams/per day for men aged 19 and older.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3013.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
GABAZOLAMINE

Approved Use

Alprazolam tablets are indicated for the management of anxiety disorder (a condition corresponding most closely to the APA Diagnostic and Statistical Manual (DSM-III-R) diagnosis of generalized anxiety disorder) or the short-term relief of symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic.
Primary
TRILIPIX

Approved Use

INDICATIONS AND USAGE Trilipix is a peroxisome proliferator-activated receptor (PPAR) alpha agonist indicated as adjunctive therapy to diet to: • Reduce TG in patients with severe hypertriglyceridemia (1.1). • Reduce elevated LDL-C, Total-C, TG and Apo B, and to increase HDLC in patients with primary hypercholesterolemia or mixed dyslipidemia (1.2). Limitations of Use: Fenofibrate at a dose equivalent to 135 mg of Trilipix did not reduce coronary heart disease morbidity and mortality in patients with type 2 diabetes mellitus (5.1).

Launch Date

2008
Primary
TRILIPIX

Approved Use

INDICATIONS AND USAGE Trilipix is a peroxisome proliferator-activated receptor (PPAR) alpha agonist indicated as adjunctive therapy to diet to: • Reduce TG in patients with severe hypertriglyceridemia (1.1). • Reduce elevated LDL-C, Total-C, TG and Apo B, and to increase HDLC in patients with primary hypercholesterolemia or mixed dyslipidemia (1.2). Limitations of Use: Fenofibrate at a dose equivalent to 135 mg of Trilipix did not reduce coronary heart disease morbidity and mortality in patients with type 2 diabetes mellitus (5.1).

Launch Date

2008
Primary
TRILIPIX

Approved Use

INDICATIONS AND USAGE Trilipix is a peroxisome proliferator-activated receptor (PPAR) alpha agonist indicated as adjunctive therapy to diet to: • Reduce TG in patients with severe hypertriglyceridemia (1.1). • Reduce elevated LDL-C, Total-C, TG and Apo B, and to increase HDLC in patients with primary hypercholesterolemia or mixed dyslipidemia (1.2). Limitations of Use: Fenofibrate at a dose equivalent to 135 mg of Trilipix did not reduce coronary heart disease morbidity and mortality in patients with type 2 diabetes mellitus (5.1).

Launch Date

2008
PubMed

PubMed

TitleDatePubMed
Imaging biochemistry: applications to breast cancer.
2001
Optimisation of the quantitative determination of chlormequat by matrix-assisted laser desorption/ionisation mass spectrometry.
2001
Hemicholinium-3 mustard reveals two populations of cycling choline cotransporters in Limulus.
2001
Glucocorticoid hypersecretion following intracerebroventricular injection of ethylcholine mustard aziridinium ion in rats.
2001
Reproducibility of proton magnetic resonance spectroscopy imaging measurements of normal human hippocampus at 1.5 T: clinical implications.
2001 Apr
Serial proton MR spectroscopic imaging of recurrent malignant gliomas after gamma knife radiosurgery.
2001 Apr
Neurotrophins differentially enhance acetylcholine release, acetylcholine content and choline acetyltransferase activity in basal forebrain neurons.
2001 Apr
Proton magnetic resonance spectroscopic imaging reveals differences in spinocerebellar ataxia types 2 and 6.
2001 Apr
Cloning of dimethylglycine dehydrogenase and a new human inborn error of metabolism, dimethylglycine dehydrogenase deficiency.
2001 Apr
Effect of AF64A, a cholinergic neurotoxin, on footshock stimulation-induced locus coeruleus excitation in rats.
2001 Apr 13
Magnetic coupling between water and creatine protons in human brain and skeletal muscle, as measured using inversion transfer (1)H-MRS.
2001 Feb
Rumen undegradable protein, rumen-protected choline and mRNA expression for enzymes in gluconeogenesis and ureagenesis in periparturient dairy cows.
2001 Feb
Characterization of the blood-brain barrier choline transporter using the in situ rat brain perfusion technique.
2001 Feb
Streptococcus pneumoniae: new tools for an old pathogen.
2001 Feb
An automated technique for the quantitative assessment of 3D-MRSI data from patients with glioma.
2001 Feb
Maintaining methylation activities during salt stress. The involvement of adenosine kinase.
2001 Feb
Reproducibility of hippocampal single-Voxel proton MR spectroscopy and chemical shift imaging.
2001 Feb
Quantitative short echo time proton magnetic resonance spectroscopic imaging study of malformations of cortical development causing epilepsy.
2001 Feb
Molecular dynamics study of active-site interactions with tetracoordinate transients in acetylcholinesterase and its mutants.
2001 Feb 1
The calcium-dependent [3H]acetylcholine release from synaptosomes of brown trout (Salmo trutta) optic tectum is inhibited by adenosine A1 receptors: effects of enucleation on A1 receptor density and cholinergic markers.
2001 Feb 16
Chronic ingestion of ethanol stimulates lipogenic response in rat hepatocytes.
2001 Feb 2
Phospholipase D-catalyzed transphosphatidylation in anhydrous organic solvents.
2001 Feb 5
Retarded myelination in the lumbar spinal cord of piglets born with spread-leg syndrome.
2001 Jan
Development and aging of the cerebrum: assessment with proton MR spectroscopy.
2001 Jan
Nicotinic agonists stimulate acetylcholine release from mouse interpeduncular nucleus: a function mediated by a different nAChR than dopamine release from striatum.
2001 Jan
Synthesis and evaluation of 18F-labeled choline as an oncologic tracer for positron emission tomography: initial findings in prostate cancer.
2001 Jan 1
Agmatine uptake by cultured hamster kidney cells.
2001 Jan 12
Pharmacological evidence for the selectivity of in vivo signals obtained with enzyme-based electrochemical sensors.
2001 Jan 15
Overexpression of a mammalian ethanolamine-specific kinase accelerates the CDP-ethanolamine pathway.
2001 Jan 19
Helicobacter pylori-induced prostaglandin E(2) synthesis involves activation of cytosolic phospholipase A(2) in epithelial cells.
2001 Jan 5
Verbal and visual memory improve after choline supplementation in long-term total parenteral nutrition: a pilot study.
2001 Jan-Feb
Imidazoline I(1) receptor-induced activation of phosphatidylcholine-specific phospholipase C elicits mitogen-activated protein kinase phosphorylation in PC12 cells.
2001 Mar
Expression of the INO2 regulatory gene of Saccharomyces cerevisiae is controlled by positive and negative promoter elements and an upstream open reading frame.
2001 Mar
Reanalysis of multislice (1)H MRSI in amyotrophic lateral sclerosis.
2001 Mar
Evaluation of accumulated mucopolysaccharides in the brain of patients with mucopolysaccharidoses by (1)H-magnetic resonance spectroscopy before and after bone marrow transplantation.
2001 Mar
Structure and expression of the murine phosphatidylserine synthase-1 gene.
2001 Mar 16
De novo synthesis and recycling pathways of sphingomyelin in rat Sertoli cells.
2001 Mar 9
Patents

Sample Use Guides

Choline tablets will be taken at daily doses of 250 mg (in children with up to 40 kg body weight) and 500 mg (in children with more than 40 kg body weight).
Route of Administration: Oral
Monolayer cultures of Primary bovine hepatocytes were maintained for 24 h and were approximately 80% confluent before exposure to treatment. Cells were randomly assigned to increasing concentrations (61, 128, 2028, and 4528 μmol/L) of choline chloride (CC), DL-methionine (DLM), and a fatty acid cocktail in a 4X4X2 factorial arrangement. All treatments were applied in triplicate in independent preparations of cells from 4 Holstein calves.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:45 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:45 GMT 2023
Record UNII
N91BDP6H0X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHOLINE
MI   VANDF   WHO-DD  
Systematic Name English
NANOVESON C
Common Name English
(.BETA.-HYDROXYETHYL)TRIMETHYLAMMONIUM
Systematic Name English
CHOLINE CATION
Common Name English
CHOLINE [VANDF]
Common Name English
2-HYDROXYETHYL)TRIMETHYLAMMONIUM
Common Name English
ACETYLCHOLINE CHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
2-HYDROXY-N,N,N-TRIMETHYLETHANAMINIUM
Systematic Name English
CHOLINE ION
Common Name English
CHOLINE [MI]
Common Name English
Choline [WHO-DD]
Common Name English
CARBACHOL IMPURITY A [EP IMPURITY]
Common Name English
VITAMIN J
Common Name English
BILINEURINE
Common Name English
Classification Tree Code System Code
LIVERTOX NBK548710
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
DSLD 39 (Number of products:4095)
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
NCI_THESAURUS C1551
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
Code System Code Type Description
CHEBI
15354
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
EVMPD
SUB13349MIG
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
EVMPD
SUB20877
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
ALTERNATIVE
MERCK INDEX
m3481
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY Merck Index
FDA UNII
N91BDP6H0X
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
WIKIPEDIA
CHOLINE
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
CAS
62-49-7
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
MESH
D002794
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
RXCUI
2449
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00122
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
NCI_THESAURUS
C61674
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
SMS_ID
100000080081
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
PUBCHEM
305
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
DRUG CENTRAL
3097
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-535-1
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID8043789
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
DAILYMED
N91BDP6H0X
Created by admin on Fri Dec 15 15:03:45 GMT 2023 , Edited by admin on Fri Dec 15 15:03:45 GMT 2023
PRIMARY
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