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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/19906248Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19906248
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL220 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9435905 |
3013.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | GABAZOLAMINE Approved UseAlprazolam 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 UseINDICATIONS 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 Date1.22929925E12 |
|||
Primary | TRILIPIX Approved UseINDICATIONS 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 Date1.22929925E12 |
|||
Primary | TRILIPIX Approved UseINDICATIONS 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 Date1.22929925E12 |
PubMed
Title | Date | PubMed |
---|---|---|
Temporal lobe changes following radiation therapy: imaging and proton MR spectroscopic findings. | 2001 |
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Biological properties and measurement of phospholipase D activation by ADP-ribosylation factor (ARF). | 2001 |
|
Hemicholinium-3 mustard reveals two populations of cycling choline cotransporters in Limulus. | 2001 |
|
Reproducibility of proton magnetic resonance spectroscopy imaging measurements of normal human hippocampus at 1.5 T: clinical implications. | 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 MR spectroscopy in clinical routine. | 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 |
|
Carrier-mediated hepatobiliary transport of a novel antifolate, N-[4-[(2,4-dianninopteridine-6-yl)methyl]-3,4-dihydro-2H-1,4-benzothiazin-7-yl]carbonyl-L-homoglutamic acid, in rats. | 2001 Apr |
|
Nutritional support at home and in the community. | 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 |
|
Blocking pulmonary ICAM-1 expression ameliorates lung injury in established diet-induced pancreatitis. | 2001 Feb |
|
Streptococcus pneumoniae: new tools for an old pathogen. | 2001 Feb |
|
In vivo and in vitro proton NMR spectroscopic studies of thiamine-deficient rat brains. | 2001 Feb |
|
Effect of N-acetylcysteine treatment on NO2-impaired type II pneumocyte surfactant metabolism. | 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 |
|
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 |
|
Menstrual cycle-related brain metabolite changes using 1H magnetic resonance spectroscopy in premenopausal women: a pilot study. | 2001 Feb 28 |
|
Increased thalamic N-acetylaspartate in male patients with familial bipolar I disorder. | 2001 Feb 28 |
|
Modulation of biosynthesis of phosphatidylcholine via CDP-choline in rat liver: influence of ethanol on the microsomal cholinephosphotransferase activity. | 2001 Jan |
|
1H MR spectroscopy evidence for the varied nature of asymptomatic focal brain lesions in neurofibromatosis type 1. | 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 |
|
Retarded myelination in the lumbar spinal cord of piglets born with spread-leg syndrome. | 2001 Jan |
|
Alterations of the transforming growth factor-beta signaling pathway in hepatocellular carcinomas induced endogenously and exogenously in rats. | 2001 Jan |
|
Plasma choline in normal newborns, infants, toddlers, and in very-low-birth-weight neonates requiring total parenteral nutrition. | 2001 Jan |
|
Development and aging of the cerebrum: assessment with proton MR spectroscopy. | 2001 Jan |
|
Regional differences and metabolic changes in normal aging of the human brain: proton MR spectroscopic imaging study. | 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 |
|
Altered cellular metabolism following traumatic brain injury: a magnetic resonance spectroscopy study. | 2001 Mar |
|
Resveratrol inhibits the formation of phosphatidic acid and diglyceride in chemotactic peptide- or phorbol ester-stimulated human neutrophils. | 2001 Mar |
|
Characterization of the deg-3/des-2 receptor: a nicotinic acetylcholine receptor that mutates to cause neuronal degeneration. | 2001 Mar |
|
The puzzle of zmpB and extensive chain formation, autolysis defect and non-translocation of choline-binding proteins in Streptococcus pneumoniae. | 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 |
|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01098383
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28152052
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
Edited
Wed Jul 05 22:35:52 UTC 2023
by
admin
on
Wed Jul 05 22:35:52 UTC 2023
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Record UNII |
N91BDP6H0X
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Record Status |
Validated (UNII)
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Record Version |
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LIVERTOX |
NBK548710
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DSLD |
39 (Number of products:4095)
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NCI_THESAURUS |
C1551
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15354
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SUB13349MIG
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SUB20877
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M3481
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N91BDP6H0X
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CHOLINE
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62-49-7
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D002794
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DB00122
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C61674
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100000080081
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305
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200-535-1
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DTXSID8043789
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