U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of BETAINE

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

HIDE SMILES / InChI

Molecular Formula C5H11NO2
Molecular Weight 117.1463
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.

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
Betaine and homocysteine concentrations in infant formulae and breast milk.
2001 Dec
Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects.
2002 Nov
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
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
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
Antioxidant defense of betaine against isoprenaline-induced myocardial infarction in rats.
2010 Mar
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
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
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
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 Wed Jul 05 22:41:54 UTC 2023
Edited
by admin
on Wed Jul 05 22:41:54 UTC 2023
Record UNII
3SCV180C9W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETAINE
FCC   FHFI   HSDB   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
BETAINE [ORANGE BOOK]
Common Name English
BETAINE [MI]
Common Name English
(TRIMETHYLAMMONIO)ACETATE
Systematic Name English
METHANAMINIUM, 1-CARBOXY-N,N,N-TRIMETHYL-
Systematic Name English
BETAINE [FCC]
Common Name English
FEMA NO. 4223
Code English
(CARBOXYMETHYL)TRIMETHYLAMMONIUM
Systematic Name English
BETAINE [HSDB]
Common Name English
BETAINE ANHYDROUS
EMA EPAR  
Common Name English
BETAINE [MART.]
Common Name English
BETAINE [USP-RS]
Common Name English
BETAINE [INCI]
Common Name English
BETAINE [VANDF]
Common Name English
NSC-166511
Code English
TRIMETHYLGLYCINE
Systematic Name English
ABROMINE
Common Name English
BETAINE [JAN]
Common Name English
Betaine [WHO-DD]
Common Name English
BETAINE, ANHYDROUS
Common Name English
BETAINE [FHFI]
Common Name English
BETAINE ANHYDROUS [EMA EPAR]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 103669
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
FDA ORPHAN DRUG 81794
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
NDF-RT N0000175805
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
NDF-RT N0000175804
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
EMA ASSESSMENT REPORTS XIAPEX (AUTHORIZED DUPUYTREN CONTRACTURE)
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
EMA ASSESSMENT REPORTS CYSTADANE (AUTHORIZED HOMOCYSTINURIA)
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
DSLD 2312 (Number of products:649)
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
WHO-ATC A16AA06
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
WHO-ATC A09AB02
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
EU-Orphan Drug EU/3/01/045
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
WHO-VATC QA16AA06
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
DSLD 625 (Number of products:495)
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
203-490-6
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
PUBCHEM
247
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
PRIMARY
RS_ITEM_NUM
1065695
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
PRIMARY
MESH
D001622
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
NCI_THESAURUS
C81038
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
DRUG CENTRAL
347
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
CONCEPT Dietary Supplement
RXCUI
350374
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
PRIMARY
CAS
107-43-7
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
DAILYMED
3SCV180C9W
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
CHEBI
17750
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
HSDB
7467
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
FDA UNII
3SCV180C9W
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
RXCUI
1512
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
ALTERNATIVE
EVMPD
SUB13055MIG
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
EVMPD
SUB23574
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
NSC
166511
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
PRIMARY
MERCK INDEX
M2451
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY Merck Index
SMS_ID
100000089335
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
PRIMARY
WIKIPEDIA
TRIMETHYLGLYCINE
Created by admin on Wed Jul 05 22:41:55 UTC 2023 , Edited by admin on Wed Jul 05 22:41:55 UTC 2023
PRIMARY
EPA CompTox
DTXSID8022666
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
DRUG BANK
DB06756
Created by admin on Wed Jul 05 22:41:54 UTC 2023 , Edited by admin on Wed Jul 05 22:41:54 UTC 2023
PRIMARY
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