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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Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney. | 1987 Mar |
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The clinical potential of ademetionine (S-adenosylmethionine) in neurological disorders. | 1994 Aug |
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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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Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine. | 1998 Sep |
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Betaine and homocysteine concentrations in infant formulae and breast milk. | 2001 Dec |
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Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects. | 2002 Nov |
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Carbon tetrachloride-induced nephrotoxicity and protective effect of betaine in Sprague-Dawley rats. | 2003 Aug |
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Homocysteine-betaine interactions in a murine model of 5,10-methylenetetrahydrofolate reductase deficiency. | 2003 Mar |
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Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells. | 2006 Nov |
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Consideration of betaine and one-carbon sources of N5-methyltetrahydrofolate for use in homocystinuria and neural tube defects. | 2007 Apr |
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Long follow up of betaine therapy in two Japanese siblings with cystathionine beta-synthase deficiency. | 2008 Oct |
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Alleviation of dimethylnitrosamine-induced liver injury and fibrosis by betaine supplementation in rats. | 2009 Feb 12 |
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Characteristics of transport of selenoamino acids by epithelial amino acid transporters. | 2009 Feb 12 |
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S-Adenosylhomocysteine increases beta-amyloid formation in BV-2 microglial cells by increased expressions of beta-amyloid precursor protein and presenilin 1 and by hypomethylation of these gene promoters. | 2009 Jul |
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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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Protective effect of betaine on changes in the levels of lysosomal enzyme activities in heart tissue in isoprenaline-induced myocardial infarction in Wistar rats. | 2009 Nov |
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Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney. | 2010 |
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Mechanism for prevention of alcohol-induced liver injury by dietary methyl donors. | 2010 May |
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S-Adenosylhomocysteine enhances DNA damage through increased β-amyloid formation and inhibition of the DNA-repair enzyme OGG1b in microglial BV-2 cells. | 2011 Dec 18 |
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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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Survival and psychomotor development with early betaine treatment in patients with severe methylenetetrahydrofolate reductase deficiency. | 2014 Feb |
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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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The organic osmolyte betaine induces keratin 2 expression in rat epidermal keratinocytes - A genome-wide study in UVB irradiated organotypic 3D cultures. | 2015 Dec 25 |
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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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A09AB02
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EU-Orphan Drug |
EU/3/01/045
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QA16AA06
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625 (Number of products:495)
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D001622
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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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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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