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Details

Stereochemistry ACHIRAL
Molecular Formula C5H11NO2.H2O
Molecular Weight 135.1618
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BETAINE HYDRATE

SMILES

C[N+](C)(C)CC(=O)[O-].O

InChI

InChIKey=NJZRLXNBGZBREL-UHFFFAOYSA-N
InChI=1S/C5H11NO2.H2O/c1-6(2,3)4-5(7)8;/h4H2,1-3H3;1H2

HIDE SMILES / InChI

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

Molecular Formula C5H12NO2
Molecular Weight 118.1545
Charge 1
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CYSTADANE

Approved Use

Cystadane 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 Date

8.4620162E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.456 mM
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
12.528 mM × h
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
41.17 h
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
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
Doses

Doses

DosePopulationAdverse events​
20 g 1 times / day multiple, oral
Highest studied dose
Dose: 20 g, 1 times / day
Route: oral
Route: multiple
Dose: 20 g, 1 times / day
Sources:
unhealthy, adult
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney.
1987 Mar
The clinical potential of ademetionine (S-adenosylmethionine) in neurological disorders.
1994 Aug
Strychnine-dependent allodynia in the urethane-anesthetized rat is segmentally distributed and prevented by intrathecal glycine and betaine.
1995 Dec
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
Effects of amplification facilitators on diagnostic PCR in the presence of blood, feces, and meat.
2000 Dec
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
Betaine, a promising new agent for patients with nonalcoholic steatohepatitis: results of a pilot study.
2001 Sep
Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects.
2002 Nov
Carbon tetrachloride-induced nephrotoxicity and protective effect of betaine in Sprague-Dawley rats.
2003 Aug
Determination of choline, betaine, and dimethylglycine in plasma by a high-throughput method based on normal-phase chromatography-tandem mass spectrometry.
2003 Feb
Homocysteine-betaine interactions in a murine model of 5,10-methylenetetrahydrofolate reductase deficiency.
2003 Mar
Betaine. Monograph.
2003 May
Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies.
2005 Aug 15
Betaine suppresses proinflammatory signaling during aging: the involvement of nuclear factor-kappaB via nuclear factor-inducing kinase/IkappaB kinase and mitogen-activated protein kinases.
2005 Oct
Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells.
2006 Nov
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
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
Alleviation of dimethylnitrosamine-induced liver injury and fibrosis by betaine supplementation in rats.
2009 Feb 12
Characteristics of transport of selenoamino acids by epithelial amino acid transporters.
2009 Feb 12
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
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
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
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney.
2010
Antioxidant defense of betaine against isoprenaline-induced myocardial infarction in rats.
2010 Mar
Mechanism for prevention of alcohol-induced liver injury by dietary methyl donors.
2010 May
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
Effects of betaine on lipopolysaccharide-induced memory impairment in mice and the involvement of GABA transporter 2.
2011 Nov 4
Chemical chaperones improve protein secretion and rescue mutant factor VIII in mice with hemophilia A.
2012
Wilson's disease: changes in methionine metabolism and inflammation affect global DNA methylation in early liver disease.
2013 Feb
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
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
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
Proteomics analysis of altered cellular metabolism induced by insufficient copper level.
2014 Nov 10
5-Methyl phenazine-1-carboxylic acid: a novel bioactive metabolite by a rhizosphere soil bacterium that exhibits potent antimicrobial and anticancer activities.
2015 Apr 25
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
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
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
by admin
on Sat Jun 26 07:21:36 UTC 2021
Edited
by admin
on Sat Jun 26 07:21:36 UTC 2021
Record UNII
TPU0ITR2BR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETAINE HYDRATE
Common Name English
(CARBOXYMETHYL)TRIMETHYLAMMONIUM HYDROXIDE
Systematic Name English
BETAINE MONOHYDRATE [MI]
Common Name English
BETAINE MONOHYDRATE
MI   WHO-DD  
Common Name English
TRIMETHYLGLYCINE HYDROXIDE
Systematic Name English
BETAINE MONOHYDRATE [WHO-DD]
Common Name English
Code System Code Type Description
CAS
590-47-6
Created by admin on Sat Jun 26 07:21:36 UTC 2021 , Edited by admin on Sat Jun 26 07:21:36 UTC 2021
PRIMARY
MERCK INDEX
M2451
Created by admin on Sat Jun 26 07:21:36 UTC 2021 , Edited by admin on Sat Jun 26 07:21:36 UTC 2021
PRIMARY Merck Index
PUBCHEM
83815
Created by admin on Sat Jun 26 07:21:36 UTC 2021 , Edited by admin on Sat Jun 26 07:21:36 UTC 2021
PRIMARY
FDA UNII
TPU0ITR2BR
Created by admin on Sat Jun 26 07:21:36 UTC 2021 , Edited by admin on Sat Jun 26 07:21:36 UTC 2021
PRIMARY
EVMPD
SUB13060MIG
Created by admin on Sat Jun 26 07:21:36 UTC 2021 , Edited by admin on Sat Jun 26 07:21:36 UTC 2021
PRIMARY
EPA CompTox
590-47-6
Created by admin on Sat Jun 26 07:21:36 UTC 2021 , Edited by admin on Sat Jun 26 07:21:36 UTC 2021
PRIMARY
ECHA (EC/EINECS)
209-684-7
Created by admin on Sat Jun 26 07:21:36 UTC 2021 , Edited by admin on Sat Jun 26 07:21:36 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE