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Details

Stereochemistry ACHIRAL
Molecular Formula C5H14NO.HO
Molecular Weight 121.1781
Optical Activity NONE
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHOLINE HYDROXIDE

SMILES

[OH-].C[N+](C)(C)CCO

InChI

InChIKey=KIZQNNOULOCVDM-UHFFFAOYSA-M
InChI=1S/C5H14NO.H2O/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H2/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula C5H14NO
Molecular Weight 104.1708
Charge 1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
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
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
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
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
Cloning of dimethylglycine dehydrogenase and a new human inborn error of metabolism, dimethylglycine dehydrogenase deficiency.
2001 Apr
Efficient synthesis of the cholinephosphate phospholipid headgroup.
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
Maintaining methylation activities during salt stress. The involvement of adenosine kinase.
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
Increased thalamic N-acetylaspartate in male patients with familial bipolar I disorder.
2001 Feb 28
Turnover of phosphatidylcholine in Saccharomyces cerevisiae. The role of the CDP-choline pathway.
2001 Feb 9
1H MR spectroscopy evidence for the varied nature of asymptomatic focal brain lesions in neurofibromatosis type 1.
2001 Jan
Cannabinoid CB1 receptor-mediated inhibition of acetylcholine release in the brain of NMRI, CD-1 and C57BL/6J mice.
2001 Jan
Overexpression of a mammalian ethanolamine-specific kinase accelerates the CDP-ethanolamine pathway.
2001 Jan 19
The characteristics of nucleobase transport and metabolism by the perfused sheep choroid plexus.
2001 Jan 5
The puzzle of zmpB and extensive chain formation, autolysis defect and non-translocation of choline-binding proteins in Streptococcus pneumoniae.
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
Vitrification of mouse oocytes using a nylon loop.
2001 Mar
Structure and expression of the murine phosphatidylserine synthase-1 gene.
2001 Mar 16
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 Mon Mar 31 17:45:32 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:32 GMT 2025
Record UNII
7THJ3EG9SY
Record Status Validated (UNII)
Record Version
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Name Type Language
CHOLINUM
HPUS  
Preferred Name English
CHOLINE HYDROXIDE
MI  
Systematic Name English
(2-HYDROXYETHYL)TRIMETHYLAMMONIUM HYDROXIDE
Systematic Name English
ETHANAMINIUM, 2-HYDROXY-N,N,N-TRIMETHYL-, HYDROXIDE
Common Name English
(.BETA.-HYDROXYETHYL)TRIMETHYLAMMONIUM HYDROXIDE
Systematic Name English
BILINEURINE HYDROXIDE
Common Name English
CHOLINE, HYDROXIDE
Common Name English
LURIDINE
Common Name English
VIDINE
Common Name English
CHOLINE HYDROXIDE [MI]
Common Name English
CHOLINUM [HPUS]
Common Name English
SINCALINE
Common Name English
GOSSYPINE
Common Name English
BURSINE
Common Name English
TRIMETHYL(HYDROXYETHYL)AMMONIUM HYDROXIDE
Systematic Name English
TRIMETHYL(2-HYDROXYETHYL)AMMONIUM HYDROXIDE
Systematic Name English
ETHANAMINIUM, 2-HYDROXY-N,N,N-TRIMETHYL-, HYDROXIDE (1:1)
Common Name English
2-HYDROXY-N,N,N-TRIMETHYLETHANAMINIUM HYDROXIDE
Systematic Name English
FAGINE
Common Name English
Code System Code Type Description
MERCK INDEX
m3481
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY Merck Index
RXCUI
1311084
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY RxNorm
DAILYMED
7THJ3EG9SY
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
EPA CompTox
DTXSID9047467
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
CAS
123-41-1
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
FDA UNII
7THJ3EG9SY
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
PUBCHEM
31255
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-625-1
Created by admin on Mon Mar 31 17:45:32 GMT 2025 , Edited by admin on Mon Mar 31 17:45:32 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY