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Details

Stereochemistry ABSOLUTE
Molecular Formula C5H14NO.C4H5O6
Molecular Weight 253.2497
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHOLINE BITARTRATE

SMILES

C[N+](C)(C)CCO.O[C@H]([C@@H](O)C([O-])=O)C(O)=O

InChI

InChIKey=QWJSAWXRUVVRLH-LREBCSMRSA-M
InChI=1S/C5H14NO.C4H6O6/c1-6(2,3)4-5-7;5-1(3(7)8)2(6)4(9)10/h7H,4-5H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/q+1;/p-1/t;1-,2-/m.1/s1

HIDE SMILES / InChI

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
Role of cholinergic mossy fibers in medial vestibular and prepositus hypoglossal nuclei in vestibular compensation.
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
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
Aging alters the multichemical networking profile of the human brain: an in vivo (1)H-MRS study of young versus middle-aged subjects.
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
Impaired neurotransmitter release from lacrimal and salivary gland nerves of a murine model of Sjögren's syndrome.
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
GD1a in phospholipid bilayer: a molecular dynamics simulation.
2001 Feb
Lactate and other metabolic changes in neuronal migration disorders.
2001 Feb
Rumen undegradable protein, rumen-protected choline and mRNA expression for enzymes in gluconeogenesis and ureagenesis in periparturient dairy cows.
2001 Feb
Chronic ingestion of ethanol stimulates lipogenic response in rat hepatocytes.
2001 Feb 2
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
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
Modulation of electrically evoked acetylcholine release in cultured rat septal neurones.
2001 Jan
Na/Li countertransport abnormalities in type 1 diabetes with and without nephropathy are familial.
2001 Mar
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
Imidazoline I(1) receptor-induced activation of phosphatidylcholine-specific phospholipase C elicits mitogen-activated protein kinase phosphorylation in PC12 cells.
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
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
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
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.
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 Fri Dec 15 15:04:02 GMT 2023
Edited
by admin
on Fri Dec 15 15:04:02 GMT 2023
Record UNII
6K2W7T9V6Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CHOLINE BITARTRATE
FCC   HSDB   MART.   MI   USP-RS   VANDF   WHO-DD  
Systematic Name English
CHOLINE BITARTRATE [MI]
Common Name English
Choline bitartrate [WHO-DD]
Common Name English
CHOLINE BITARTRATE [HSDB]
Common Name English
CHOLINE BITARTRATE [FCC]
Common Name English
CHOLINE (AS BITARTRATE) [VANDF]
Common Name English
CHOLINE BITARTRATE [VANDF]
Common Name English
CHOLINE BITARTRATE [MART.]
Common Name English
2-HYDROXYETHANAMINIUM,-N,N,N-TRIMETHYL-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Common Name English
CHOLINE BITARTRATE [USP-RS]
Common Name English
(2-HYDROXYETHYL)TRIMETHYLAMMONIUM-L-(+)-TARTRATE SALT (1:1)
Common Name English
CHOLINE (AS BITARTRATE)
VANDF  
Common Name English
Classification Tree Code System Code
CFR 21 CFR 331.11
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
FDA ORPHAN DRUG 299909
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C76834
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
PUBCHEM
6900
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID00889332
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
HSDB
983
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
RXCUI
2451
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY RxNorm
FDA UNII
6K2W7T9V6Y
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
MERCK INDEX
m3481
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
201-763-4
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
CONCEPT Dietary Supplement
SMS_ID
100000085189
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PRIMARY
RS_ITEM_NUM
1133536
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
EVMPD
SUB13350MIG
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105935
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
DAILYMED
6K2W7T9V6Y
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
DRUG BANK
DBSALT001542
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
CAS
87-67-2
Created by admin on Fri Dec 15 15:04:02 GMT 2023 , Edited by admin on Fri Dec 15 15:04:02 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY