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Details

Stereochemistry ACHIRAL
Molecular Formula C5H14NO
Molecular Weight 104.171
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 103.163
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

1.22929925E12
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

1.22929925E12
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

1.22929925E12
PubMed

PubMed

TitleDatePubMed
Animal models of steatosis.
2001
Imaging biochemistry: applications to breast cancer.
2001
Glucose plus choline improve passive avoidance behaviour and increase hippocampal acetylcholine release in mice.
2001
Optimisation of the quantitative determination of chlormequat by matrix-assisted laser desorption/ionisation mass spectrometry.
2001
Temporal lobe changes following radiation therapy: imaging and proton MR spectroscopic findings.
2001
Hemicholinium-3 mustard reveals two populations of cycling choline cotransporters in Limulus.
2001
In vivo 1H magnetic resonance spectroscopic measurement of brain glycine levels in nonketotic hyperglycinemia.
2001 Apr
Reproducibility of proton magnetic resonance spectroscopy imaging measurements of normal human hippocampus at 1.5 T: clinical implications.
2001 Apr
Lateralizing ability of single-voxel proton mr spectroscopy in hippocampal sclerosis: comparison with mr imaging and positron emission tomography.
2001 Apr
Serial proton MR spectroscopic imaging of recurrent malignant gliomas after gamma knife radiosurgery.
2001 Apr
Preoperative proton MR spectroscopic imaging of brain tumors: correlation with histopathologic analysis of resection specimens.
2001 Apr
Theta-frequency facilitation of AMPA receptor-mediated synaptic currents in the principal cells of the medial septum.
2001 Apr
Neurotrophins differentially enhance acetylcholine release, acetylcholine content and choline acetyltransferase activity in basal forebrain neurons.
2001 Apr
Overactivation of alpha-amino-3-hydroxy-5-methylisoxazole-4-propionate and N-methyl-D-aspartate but not kainate receptors inhibits phosphatidylcholine synthesis before excitotoxic neuronal death.
2001 Apr
Proton magnetic resonance spectroscopic imaging reveals differences in spinocerebellar ataxia types 2 and 6.
2001 Apr
Magnetic resonance spectroscopy in traumatic brain injury.
2001 Apr
Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome.
2001 Apr
Lysosomal-type PLA2 and turnover of alveolar DPPC.
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
Efficient synthesis of the cholinephosphate phospholipid headgroup.
2001 Feb
A novel method to analyze betaine in chicken liver: effect of dietary betaine and choline supplementation on the hepatic betaine concentration in broiler chicks.
2001 Feb
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
Intestinal uptake of betaine in vitro and the distribution of methyl groups from betaine, choline, and methionine in the body of broiler chicks.
2001 Feb
Characteristics of fast Na(+) current of hypoglossal motoneurons in a rat brainstem slice preparation.
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
In vivo and in vitro proton NMR spectroscopic studies of thiamine-deficient rat brains.
2001 Feb
Molecular dynamics study of active-site interactions with tetracoordinate transients in acetylcholinesterase and its mutants.
2001 Feb 1
Menstrual cycle-related brain metabolite changes using 1H magnetic resonance spectroscopy in premenopausal women: a pilot study.
2001 Feb 28
Three-dimensional magnetic resonance spectroscopic imaging of histologically confirmed brain tumors.
2001 Jan
Modulation of biosynthesis of phosphatidylcholine via CDP-choline in rat liver: influence of ethanol on the microsomal cholinephosphotransferase activity.
2001 Jan
Aging alters regional multichemical profile of the human brain: an in vivo 1H-MRS study of young versus middle-aged subjects.
2001 Jan
Modulation of electrically evoked acetylcholine release in cultured rat septal neurones.
2001 Jan
Protein kinase C activation by 12-0-tetradecanoylphorbol 13-acetate in CG-4 line oligodendrocytes stimulates turnover of choline and ethanolamine phospholipids by phospholipase D and induces rapid process contraction.
2001 Jan
Apical uptake of organic cations by human intestinal Caco-2 cells: putative involvement of ASF transporters.
2001 Jan
Alterations of the transforming growth factor-beta signaling pathway in hepatocellular carcinomas induced endogenously and exogenously in rats.
2001 Jan
Improving diagnostic yield in brain biopsy: coupling spectroscopic targeting with real-time needle placement.
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
Na/Li countertransport abnormalities in type 1 diabetes with and without nephropathy are familial.
2001 Mar
Characterization of the deg-3/des-2 receptor: a nicotinic acetylcholine receptor that mutates to cause neuronal degeneration.
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
Sustained bilateral hemodynamic benefit of contralateral carotid endarterectomy in patients with symptomatic internal carotid artery occlusion.
2001 Mar
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.
2001 Mar
Vitrification of mouse oocytes using a nylon loop.
2001 Mar
Magnetic resonance spectroscopy in AD.
2001 Mar 13
De novo synthesis and recycling pathways of sphingomyelin in rat Sertoli cells.
2001 Mar 9
The biochemical analysis of neurotransmitters in central neurocytomas.
2001 May
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 Sat Jun 26 06:48:17 UTC 2021
Edited
by admin
on Sat Jun 26 06:48:17 UTC 2021
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
2-HYDROXY-N,N,N-TRIMETHYLETHANAMINIUM
Systematic Name English
CHOLINE ION
Common Name English
CHOLINE [MI]
Common Name English
VITAMIN J
Common Name English
CHOLINE [WHO-DD]
Common Name English
BILINEURINE
Common Name English
Classification Tree Code System Code
LIVERTOX 203
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
DSLD 39 (Number of products:4095)
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
NCI_THESAURUS C1551
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
Code System Code Type Description
EVMPD
SUB13349MIG
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
EVMPD
SUB20877
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
ALTERNATIVE
MERCK INDEX
M3481
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY Merck Index
FDA UNII
N91BDP6H0X
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
WIKIPEDIA
CHOLINE
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
CAS
62-49-7
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
MESH
D002794
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
RXCUI
2449
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00122
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
NCI_THESAURUS
C61674
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
PUBCHEM
305
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
DRUG CENTRAL
3097
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-535-1
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
EPA CompTox
62-49-7
Created by admin on Sat Jun 26 06:48:19 UTC 2021 , Edited by admin on Sat Jun 26 06:48:19 UTC 2021
PRIMARY
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