Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H11NO2 |
Molecular Weight | 117.1463 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[N+](C)(C)CC([O-])=O
InChI
InChIKey=KWIUHFFTVRNATP-UHFFFAOYSA-N
InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
Betaine is a methyl derivative of glycine first isolated from the juice of sugar beets. Betaine is found in many common foods, but concentrated significantly in beets, spinach, wheat foods, and shellfish. In addition, betaine can be synthesized within the human body. Betaine participates in the methionine cycle, which produces vital biomolecules including proteins, hormones, phospholipids, polyamines, and nutrients. Betaine is used as a dietary supplement and has a beneficial effect on the human health. In the USA, FDA approved a betaine-containing drug Cystadane for the treatment of homocystinuria. The drug acts as a methyl group donor in the remethylation of homocysteine to methionine.
CNS Activity
Approval Year
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | CYSTADANE Approved UseCystadane is a methylating agent indicated for the treatment of homocystinuria to decrease elevated homocysteine blood levels. Included within the category of homocystinuria are Cystathionine beta-synthase (CBS) deficiency, 5,10-methylenetetrahydrofolate reductase (MTHFR) deficiency, Cobalamin cofactor metabolism (cbl) defect. Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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1.456 mM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635 |
50 mg/kg bw 2 times / day multiple, oral dose: 50 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
BETAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
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0.939 mM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
BETAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.528 mM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635 |
50 mg/kg bw 2 times / day multiple, oral dose: 50 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
BETAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
5.518 mM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
BETAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
41.17 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635 |
50 mg/kg bw 2 times / day multiple, oral dose: 50 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered: |
BETAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
14.38 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635 |
50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered: |
BETAINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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Strychnine-dependent allodynia in the urethane-anesthetized rat is segmentally distributed and prevented by intrathecal glycine and betaine. | 1995 Dec |
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Cerebrospinal fluid and plasma total homocysteine and related metabolites in children with cystathionine beta-synthase deficiency: the effect of treatment. | 1997 Nov |
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Betaine and homocysteine concentrations in infant formulae and breast milk. | 2001 Dec |
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An open-label, 24-week pilot study of the methyl donor betaine in Alzheimer disease patients. | 2001 Jul-Sep |
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Betaine, a promising new agent for patients with nonalcoholic steatohepatitis: results of a pilot study. | 2001 Sep |
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Carbon tetrachloride-induced nephrotoxicity and protective effect of betaine in Sprague-Dawley rats. | 2003 Aug |
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Determination of choline, betaine, and dimethylglycine in plasma by a high-throughput method based on normal-phase chromatography-tandem mass spectrometry. | 2003 Feb |
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Betaine. Monograph. | 2003 May |
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Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies. | 2005 Aug 15 |
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Assessment of the effect of betaine on p16 and c-myc DNA methylation and mRNA expression in a chemical induced rat liver cancer model. | 2009 Jul 30 |
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Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney. | 2010 |
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Effects of betaine on lipopolysaccharide-induced memory impairment in mice and the involvement of GABA transporter 2. | 2011 Nov 4 |
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Chemical chaperones improve protein secretion and rescue mutant factor VIII in mice with hemophilia A. | 2012 |
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Wilson's disease: changes in methionine metabolism and inflammation affect global DNA methylation in early liver disease. | 2013 Feb |
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A urinary metabonomics study on biochemical changes in yeast-induced pyrexia rats: a new approach to elucidating the biochemical basis of the febrile response. | 2013 Jun 25 |
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Betaine supplementation protects against renal injury induced by cadmium intoxication in rats: role of oxidative stress and caspase-3. | 2014 Mar |
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Proteomics analysis of altered cellular metabolism induced by insufficient copper level. | 2014 Nov 10 |
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Regulation of signal transducer and activator of transcription 3 and apoptotic pathways by betaine attenuates isoproterenol-induced acute myocardial injury in rats. | 2015 May |
Patents
Sample Use Guides
The usual dosage in adult and pediatric patients is 6 grams per day administered orally in divided doses of 3 grams twice daily. In pediatric patients less than 3 years of age, dosage may be started at 100 mg/kg/day divided in twice daily doses, and then increased weekly by 50 mg/kg increments.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25921120
HeLa cells were treated with 0.1, 1.0, 5.0, 20.0, 100.0 mg/ml of betaine to evaluate the anticancer efficacy of the compound. The percentage of S phase cells in the low dose groups (< 5mg/ml) were distinctly higher than in high dose groups, and the rates of Sub-G1 phase were the opposite. A high concentration of betaine (>5.0mg/ml) significantly promoted the apoptosis of HeLa cells.
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EPA PESTICIDE CODE |
103669
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FDA ORPHAN DRUG |
81794
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NDF-RT |
N0000175805
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N0000175804
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EMA ASSESSMENT REPORTS |
XIAPEX (AUTHORIZED DUPUYTREN CONTRACTURE)
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EMA ASSESSMENT REPORTS |
CYSTADANE (AUTHORIZED HOMOCYSTINURIA)
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DSLD |
2312 (Number of products:649)
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WHO-ATC |
A16AA06
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WHO-ATC |
A09AB02
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EU-Orphan Drug |
EU/3/01/045
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WHO-VATC |
QA16AA06
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625 (Number of products:495)
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203-490-6
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247
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1065695
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D001622
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C81038
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C1505
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CONCEPT | Dietary Supplement | ||
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350374
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107-43-7
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SUB13055MIG
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SUB23574
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m2451
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100000089335
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TRIMETHYLGLYCINE
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DTXSID8022666
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DB06756
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ACTIVE MOIETY
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