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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
Structure of BETAINE HYDRATE

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

HIDE SMILES / InChI

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.

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
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
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 Fri Dec 15 15:00:50 UTC 2023
Edited
by admin
on Fri Dec 15 15:00:50 UTC 2023
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 Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY
MERCK INDEX
m2451
Created by admin on Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY Merck Index
PUBCHEM
83815
Created by admin on Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY
FDA UNII
TPU0ITR2BR
Created by admin on Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY
EVMPD
SUB13060MIG
Created by admin on Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID7049421
Created by admin on Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY
SMS_ID
100000077392
Created by admin on Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
209-684-7
Created by admin on Fri Dec 15 15:00:50 UTC 2023 , Edited by admin on Fri Dec 15 15:00:50 UTC 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE