Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H11NO2 |
Molecular Weight | 117.1465 |
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
Molecular Formula | C5H11NO2 |
Molecular Weight | 117.1465 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Date8.4620162E11 |
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 |
|
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 |
---|---|---|
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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Strychnine-dependent allodynia in the urethane-anesthetized rat is segmentally distributed and prevented by intrathecal glycine and betaine. | 1995 Dec |
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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 |
|
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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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 |
|
Betaine-homocysteine S-methyltransferase-2 is an S-methylmethionine-homocysteine methyltransferase. | 2008 Apr 4 |
|
Long follow up of betaine therapy in two Japanese siblings with cystathionine beta-synthase deficiency. | 2008 Oct |
|
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 |
|
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney. | 2010 |
|
Effects of betaine on lipopolysaccharide-induced memory impairment in mice and the involvement of GABA transporter 2. | 2011 Nov 4 |
|
Dietary supplementation with methyl donors reduces fatty liver and modifies the fatty acid synthase DNA methylation profile in rats fed an obesogenic diet. | 2013 Jan |
|
Alterations in hepatic metabolism of sulfur amino acids in non-obese type-2 diabetic Goto-Kakizaki rats. | 2013 Jul 5 |
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Survival and psychomotor development with early betaine treatment in patients with severe methylenetetrahydrofolate reductase deficiency. | 2014 Feb |
|
Betaine supplementation protects against renal injury induced by cadmium intoxication in rats: role of oxidative stress and caspase-3. | 2014 Mar |
|
Betanin reduces the accumulation and cross-links of collagen in high-fructose-fed rat heart through inhibiting non-enzymatic glycation. | 2015 Feb 5 |
|
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.
Substance Class |
Chemical
Created
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admin
on
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Sat Jun 26 09:17:44 UTC 2021
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on
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Record UNII |
3SCV180C9W
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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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NDF-RT |
N0000175804
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EMA ASSESSMENT REPORTS |
XIAPEX (AUTHORIZED DUPUYTREN CONTRACTURE)
Created by
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EMA ASSESSMENT REPORTS |
CYSTADANE (AUTHORIZED HOMOCYSTINURIA)
Created by
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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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DSLD |
625 (Number of products:495)
Created by
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203-490-6
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247
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D001622
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C81038
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347
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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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7467
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3SCV180C9W
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1512
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SUB13055MIG
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SUB23574
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1065695
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PRIMARY | USP-RS | ||
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M2451
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PRIMARY | Merck Index | ||
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TRIMETHYLGLYCINE
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107-43-7
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DB06756
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