Glycine betaine
Identification
- Name
- Glycine betaine
- Accession Number
- DB06756
- Description
Betaine is a methyl group donor that functions in the normal metabolic cycle of methionine and reduces homocystinuria in patients with inborn errors of methionine metabolism. In the United States, betaine is distributed under the brand name Cystadane® by Rare Disease Therapeutics. Many reports have shown that betaine's therapeutic effectiveness is limited, and does not lower tHcy levels or prevent clinical symptoms [2].
- Type
- Small Molecule
- Groups
- Approved, Nutraceutical
- Structure
Structure for Glycine betaine (DB06756)
- Weight
- Average: 117.1463
Monoisotopic: 117.078978601 - Chemical Formula
- C5H11NO2
- Synonyms
- 2-(Trimethylammonio)Acetate
- 2-N,N,N-trimethylammonio acetate
- 2-trimethylammonioacetate
- abromine
- acidol
- betaína anhidra
- Betaine
- Betaine, anhydrous
- Glycinebetaine
- N,N,N-trimethylammonioacetate
- N,N,N-Trimethylglycine
- TMG
- Trimethylaminoacetate
- Trimethylammonioacetate
- Trimethylglycine
- trimethylglycocoll
- External IDs
- FEMA NO. 4223
- NSC-166511
Pharmacology
- Indication
Betaine is indicated for the treatment of homocystinuria to decrease elevated homocysteine blood levels. Included within the category of homocystinuria are deficiencies or defects in: 1. cystathionine beta-synthase (CBS), 2. 5,10-methylenetetrahydrofolate reductase (MTHFR), 3. cobalamin cofactor metabolism (cbl).
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Betaine acts as a methyl group donor in the remethylation of homocysteine to methionine in patients with homocystinuria.
Target Actions Organism UApoptosis regulator Bcl-2 Not Available Humans - Absorption
After a single oral dose of betaine (50 mg/kg), absorption was rapid (tmax = 0.9 ± 0.3 hours and a Cmax = 0.9 ± 0.2 mM).
- Volume of distribution
V/F = 1.3 l/kg
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
14 hours
- Clearance
84 ml/h/kg
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
In an acute toxicology study in rats, death frequently occurred at doses equal to or greater than 10,000 mg/kg.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAcebutolol Glycine betaine may increase the bradycardic activities of Acebutolol. Acetylcholine The risk or severity of adverse effects can be increased when Glycine betaine is combined with Acetylcholine. Aclidinium Glycine betaine may increase the neuromuscular blocking activities of Aclidinium. Amantadine The therapeutic efficacy of Amantadine can be decreased when used in combination with Glycine betaine. Amifampridine The risk or severity of adverse effects can be increased when Glycine betaine is combined with Amifampridine. Amitriptyline The therapeutic efficacy of Amitriptyline can be decreased when used in combination with Glycine betaine. Amobarbital The therapeutic efficacy of Amobarbital can be decreased when used in combination with Glycine betaine. Amoxapine The therapeutic efficacy of Amoxapine can be decreased when used in combination with Glycine betaine. Anisotropine methylbromide The therapeutic efficacy of Anisotropine methylbromide can be decreased when used in combination with Glycine betaine. Aripiprazole The therapeutic efficacy of Aripiprazole can be decreased when used in combination with Glycine betaine. Additional Data Available- Extended DescriptionExtended DescriptionAvailable for Purchase
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - SeveritySeverityAvailable for Purchase
A severity rating for each drug interaction, from minor to major.
Learn more - Evidence LevelEvidence LevelAvailable for Purchase
A rating for the strength of the evidence supporting each drug interaction.
Learn more - ActionActionAvailable for Purchase
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with or without food. Oral betaine powder should be mixed with food or a beverage and then consumed.
Products
Purchasing individual compounds or compound libraries for your research?
Learn More- Product Ingredients
Ingredient UNII CAS InChI Key Betaine citrate 19JX795NXV 17671-50-0 YKXUOESQDCXGIW-UHFFFAOYSA-M Betaine hydrochloride JK8U8K4D6K 590-46-5 HOPSCVCBEOCPJZ-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCystadane Powder, for solution 1 g/1g Oral Recordati Rare Diseases 1996-10-25 Not applicable US 
Cystadane Powder 1 g Oral Orphan Europe S.A.R.L. 2007-02-15 Not applicable EU 
Cystadane Powder, for solution 1 g/1g Oral Orphan Europe Sarl 2018-01-08 Not applicable US Cystadane Powder, for solution 6 g/1 Oral Rare Disease Therapeutics, Inc. 1996-10-25 Not applicable US Cystadane Powder, for solution 1 g Oral Recordati Rare Diseases Canada Inc 1998-08-11 Not applicable Canada 
Cystadane Powder, for solution 1 g/1g Oral Ropack Inc. 2017-04-13 Not applicable US Cystadane Powder, for solution 180 g/1g Oral Jazz Pharmaceuticals 2007-03-31 Not applicable US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataATONO2 Oxygen Baby Lotion 0.2 g/100g Topical Laorganic Co., Ltd. 2015-09-01 Not applicable US Betaine HCl Tab 500mg Tablet Oral Gahler Enterprises Ltd. 1991-12-31 2001-01-04 Canada Dr.g Pore Purifing Toner Liquid 0.5 g/100mL Topical GOWOONSESANG COSMETICS CO., LTD. 2015-07-05 2018-01-09 US Additional Data Available- Application NumberApplication NumberAvailable for Purchase
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct CodeAvailable for Purchase
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acididyn Tab Betaine hydrochloride (178.2 mg) + Ammonium chloride (32.4 mg) Tablet Oral Nutri Dyn Products Ltd. 1975-12-31 1997-08-22 Canada Alka-pan Tablets Betaine hydrochloride (20 mg) + Bromelains (50 mg) + Ox bile extract (35 mg) + Pancrelipase (135 mg) + Papaya (125 mg) Tablet Oral Morter Healthsystem Not applicable Not applicable Canada Bemosin Tab Betaine hydrochloride (130 mg) + Ammonium chloride (97.2 mg) + Pepsin (130 mg) Tablet Oral Therapeutic Foods Co. 1988-12-31 2003-07-16 Canada Betacol Betaine hydrochloride (61 mg) + Calcium glycerophosphate (50 mg) + Choline bitartrate (2.5 mg) + Potassium bicarbonate (41 mg) Capsule Oral Therapeutic Foods Co. 1989-12-15 1996-09-09 Canada Betaine HCl and Pepsin Betaine hydrochloride (324 mg) + Pepsin (135 mg) Tablet Oral Rheingold Food International Ltd. 1985-12-31 2007-07-26 Canada Betasin Tab Betaine hydrochloride (130 mg) + Ammonium chloride (97.2 mg) + Pepsin (130 mg) Tablet Oral Bio Vita 1987-12-31 1996-09-09 Canada Dygest Betaine hydrochloride (90 mg) + Ox bile extract (75 mg) + Pancrelipase (200 mg) + Papain (100 mg) + Peppermint (50 mg) + Pepsin (125 mg) Tablet Oral Creative Nutrition Canada Corp. 1987-12-31 2007-07-11 Canada Enzyme Tablets Betaine hydrochloride (65 mg) + Ox bile extract (8.125 mg) + Pancrelipase (100 mg) + Pancrelipase amylase (130 mg) + Papain (65 mg) + Pepsin (65 mg) Tablet Oral General Nutrition Canada Inc. 2001-10-20 2007-08-01 Canada Face It Hd Perfect Bb Spf30 Pa 01 Glycine betaine (2 mL/100mL) + Octinoxate (6 mL/100mL) + Talc (0.684 mL/100mL) + Titanium dioxide (6.36 mL/100mL) + Zinc oxide (2.88 mL/100mL) Cream Topical Thefaceshop Co., Ltd. 2011-08-23 Not applicable US Face It Hd Perfect Bb Spf30 Pa 02 Glycine betaine (2 mL/100mL) + Octinoxate (6 mL/100mL) + Talc (0.684 mL/100mL) + Titanium dioxide (6.36 mL/100mL) + Zinc oxide (2.88 mL/100mL) Cream Topical Thefaceshop Co., Ltd. 2011-08-23 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ATONO2 Oxygen Baby Glycine betaine (0.2 g/100g) Lotion Topical Laorganic Co., Ltd. 2015-09-01 Not applicable US Cystadane Glycine betaine (1 g/1g) Powder, for solution Oral Orphan Europe Sarl 2018-01-08 Not applicable US Dr.g Pore Purifing Toner Glycine betaine (0.5 g/100mL) Liquid Topical GOWOONSESANG COSMETICS CO., LTD. 2015-07-05 2018-01-09 US EnBrace HR Glycine betaine (500 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Cobamamide (50 ug/1) + Cocarboxylase (25 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic acid (1 mg/1) + Magnesium L-threonate (1 mg/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (5.23 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal phosphate (25 ug/1) + Zinc ascorbate (1 mg/1) Capsule, delayed release pellets Oral Jaymac Pharmaceuticals, Llc 2011-08-12 Not applicable US EnLyte Glycine betaine (500 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Citric acid monohydrate (1.83 mg/1) + Cobamamide (50 ug/1) + Cocarboxylase (25 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic acid (1 mg/1) + Magnesium L-threonate (1 mg/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1) + Magnesium ascorbate (24 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal phosphate (25 ug/1) + Sodium citrate (3.67 mg/1) + Zinc ascorbate (1 mg/1) Capsule, delayed release pellets Oral Jaymac Pharmaceuticals Llc 2011-08-12 Not applicable US HWASAMONG Dr.All Scalp HealingShampoo Glycine betaine (0.5 g/100mL) + Panthenol (0.3 g/100mL) Shampoo Topical Eolracellbio Co., Ltd. 2020-05-03 Not applicable US Wizyoung Diamond Collagen Essence Mask Pack Glycine betaine (0.75 g/25g) + Scutellaria baicalensis root (0.0025 g/25g) Patch Topical Wizyoung Co., Ltd 2016-11-28 Not applicable US Wizyoung Vitamin Collagen Essence Mask Pack Glycine betaine (0.75 g/25g) + Scutellaria baicalensis root (0.0025 g/25g) Patch Topical Wizyoung Co., Ltd 2016-11-28 Not applicable US
Categories
- ATC Codes
- A16AA06 — Betaine
- A16AA — Amino acids and derivatives
- A16A — OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS
- A16 — OTHER ALIMENTARY TRACT AND METABOLISM PRODUCTS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Acid Preparations
- Alimentary Tract and Metabolism
- Amines
- Amino Acids and Derivatives
- Ammonium Compounds
- Cholinesterase Inhibitors
- Digestives, Incl. Enzymes
- Gastrointestinal Agents
- Hypolipidemic Agents
- Lipid Regulating Agents
- Lipotropic Agents
- Methylating Activity
- Methylating Agent
- Nitrogen Compounds
- Noxae
- Onium Compounds
- Other Miscellaneous Therapeutic Agents
- Quaternary Ammonium Compounds
- Toxic Actions
- Trimethyl Ammonium Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids
- Alternative Parents
- Tetraalkylammonium salts / Carboxylic acid salts / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic salts / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds / Amines
- Substituents
- Aliphatic acyclic compound / Alpha-amino acid / Amine / Carbonyl group / Carboxylic acid / Carboxylic acid salt / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- glycine derivative, amino-acid betaine (CHEBI:17750) / a methylated methyl acceptor (BETAINE)
Chemical Identifiers
- UNII
- 3SCV180C9W
- CAS number
- 107-43-7
- InChI Key
- KWIUHFFTVRNATP-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
- IUPAC Name
- 2-(trimethylazaniumyl)acetate
- SMILES
- C[N+](C)(C)CC([O-])=O
References
- General References
- Diekman EF, de Koning TJ, Verhoeven-Duif NM, Rovers MM, van Hasselt PM: Survival and psychomotor development with early betaine treatment in patients with severe methylenetetrahydrofolate reductase deficiency. JAMA Neurol. 2014 Feb;71(2):188-94. doi: 10.1001/jamaneurol.2013.4915. [PubMed:24323041]
- Yokoi K, Ito T, Ohkubo Y, Sumi S, Ueta A, Sugiyama N, Togari H: Long follow up of betaine therapy in two Japanese siblings with cystathionine beta-synthase deficiency. Pediatr Int. 2008 Oct;50(5):694-5. doi: 10.1111/j.1442-200X.2008.02717.x. [PubMed:19261122]
- External Links
- Human Metabolome Database
- HMDB0000043
- KEGG Drug
- D07523
- KEGG Compound
- C00719
- PubChem Compound
- 247
- PubChem Substance
- 310264879
- ChemSpider
- 242
- BindingDB
- 50103520
- 1512
- ChEBI
- 17750
- ChEMBL
- CHEMBL1182
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Trimethylglycine
- AHFS Codes
- 56:16.00 — Digestants
- 92:92.00 — Other Miscellaneous Therapeutic Agents
- FDA label
- Download (35.7 KB)
- MSDS
- Download (47.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Arsenic Metabolites Measured in Urine 1 4 Completed Treatment Unipolar Depression 1 4 Withdrawn Treatment Menstrual Related Mood Disorder / Premenstrual Dysphoric Disorder / Premenstrual Syndrome / Premenstrual tension with edema 1 3 Completed Treatment Peroxisome Biogenesis Disorder (PBD) 1 2 Completed Treatment Homocystinuria 1 2 Completed Treatment Hyperoxaluria 1 2 Completed Treatment Nonalcoholic Steatohepatitis 1 2 Unknown Status Other BMI >30 kg/m2 / Dysglycaemia 1 2, 3 Completed Treatment Hepatitis C Viral Infection 1 1 Completed Basic Science Healthy Volunteers 2
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Lotion Topical 0.2 g/100g Capsule Oral Tablet Oral Powder Oral 1 g Powder, for solution Oral 1 g/1g Powder, for solution Oral 180 g/1g Powder, for solution Oral 6 g/1 Powder, for solution Oral 1 g Liquid Topical 0.5 g/100mL Capsule, delayed release pellets Oral Tablet Oral 100 mg Cream Topical Shampoo Topical Kit Oral Tablet Oral Tablet Oral 40 mcg Patch Topical - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.86 mg/mL ALOGPS logP -2.7 ALOGPS logP -4.5 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 2.26 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 40.13 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 52.82 m3·mol-1 ChemAxon Polarizability 12.11 Å3 ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- Results in downregulation of the target.
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Suppresses apoptosis in a variety of cell systems including factor-dependent lymphohematopoietic and neural cells. Regulates cell death by controlling the mitochondrial membrane permeability. Appea...
- Gene Name
- BCL2
- Uniprot ID
- P10415
- Uniprot Name
- Apoptosis regulator Bcl-2
- Molecular Weight
- 26265.66 Da
References
- Kennedy RK, Naik PR, Veena V, Lakshmi BS, Lakshmi P, Krishna R, Sakthivel N: 5-Methyl phenazine-1-carboxylic acid: a novel bioactive metabolite by a rhizosphere soil bacterium that exhibits potent antimicrobial and anticancer activities. Chem Biol Interact. 2015 Apr 25;231:71-82. doi: 10.1016/j.cbi.2015.03.002. Epub 2015 Mar 9. [PubMed:25765238]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Identical protein binding
- Specific Function
- Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
- Gene Name
- BCHE
- Uniprot ID
- P06276
- Uniprot Name
- Cholinesterase
- Molecular Weight
- 68417.575 Da
References
- Zhukovskii IuG, Kuznetsova LP, Sochilina EE, Dmitrieva EN, Gololobov IuG, Bykovskaia EIu: [Inhibition of cholinesterases of varying origin by ordinary and betaine vinylphosphates]. Ukr Biokhim Zh (1978). 1996 Sep-Oct;68(5):15-20. [PubMed:9229847]
- Lisa TA, Garrido MN, Domenech CE: Induction of acid phosphatase and cholinesterase activities in Ps. aeruginosa and their in-vitro control by choline, acetylcholine and betaine. Mol Cell Biochem. 1983;50(2):149-55. [PubMed:6406829]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proline dehydrogenase activity
- Specific Function
- Converts proline to delta-1-pyrroline-5-carboxylate.
- Gene Name
- PRODH
- Uniprot ID
- O43272
- Uniprot Name
- Proline dehydrogenase 1, mitochondrial
- Molecular Weight
- 68001.405 Da
References
- Jaleel CA, Manivannan P, Sankar B, Kishorekumar A, Panneerselvam R: Calcium chloride effects on salinity-induced oxidative stress, proline metabolism and indole alkaloid accumulation in Catharanthus roseus. C R Biol. 2007 Sep;330(9):674-83. Epub 2007 Aug 10. [PubMed:17720584]
- Jaleel CA, Manivannan P, Sankar B, Kishorekumar A, Gopi R, Somasundaram R, Panneerselvam R: Water deficit stress mitigation by calcium chloride in Catharanthus roseus: effects on oxidative stress, proline metabolism and indole alkaloid accumulation. Colloids Surf B Biointerfaces. 2007 Oct 15;60(1):110-6. Epub 2007 Jun 14. [PubMed:17643271]
- Jaleel CA, Manivannan P, Lakshmanan GM, Sridharan R, Panneerselvam R: NaCl as a physiological modulator of proline metabolism and antioxidant potential in Phyllanthus amarus. C R Biol. 2007 Nov;330(11):806-13. Epub 2007 Sep 25. [PubMed:17923374]
- Jaleel CA, Manivannan P, Kishorekumar A, Sankar B, Gopi R, Somasundaram R, Panneerselvam R: Alterations in osmoregulation, antioxidant enzymes and indole alkaloid levels in Catharanthus roseus exposed to water deficit. Colloids Surf B Biointerfaces. 2007 Oct 1;59(2):150-7. Epub 2007 May 6. [PubMed:17560094]
Drug created on September 14, 2010 10:21 / Updated on November 30, 2020 13:38
