Details
Stereochemistry | ACHIRAL |
Molecular Formula | C5H11NO2.H2O |
Molecular Weight | 135.1616 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.C[N+](C)(C)CC([O-])=O
InChI
InChIKey=NJZRLXNBGZBREL-UHFFFAOYSA-N
InChI=1S/C5H11NO2.H2O/c1-6(2,3)4-5(7)8;/h4H2,1-3H3;1H2
Molecular Formula | C5H12NO2 |
Molecular Weight | 118.1543 |
Charge | 1 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
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 |
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 |
---|---|---|---|---|
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 |
---|---|---|---|---|
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 |
---|---|---|
Cerebrospinal fluid and plasma total homocysteine and related metabolites in children with cystathionine beta-synthase deficiency: the effect of treatment. | 1997 Nov |
|
Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine. | 1998 Sep |
|
Maternal methyl supplements increase offspring DNA methylation at Axin Fused. | 2006 Sep |
|
Consideration of betaine and one-carbon sources of N5-methyltetrahydrofolate for use in homocystinuria and neural tube defects. | 2007 Apr |
|
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney. | 2010 |
|
Wilson's disease: changes in methionine metabolism and inflammation affect global DNA methylation in early liver disease. | 2013 Feb |
|
Betaine supplementation protects against renal injury induced by cadmium intoxication in rats: role of oxidative stress and caspase-3. | 2014 Mar |
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
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Edited
Fri Dec 15 15:00:50 UTC 2023
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Record UNII |
TPU0ITR2BR
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Record Status |
Validated (UNII)
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Record Version |
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m2451
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83815
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TPU0ITR2BR
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209-684-7
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |