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Lipoic Acid

Catalog No. DB00166 Name DrugBank
CAS Number 62-46-4 Website http://www.ualberta.ca/
M. F. C8H14O2S2 Telephone (780) 492-3111
M. W. 206.32556 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 51

SYNONYMS

IUPAC name
5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
IUPAC Traditional name
lipoic acid
Brand Name
Thioctsan
Biletan
Heparlipon
Synonyms
alpha-Lipoic acid
Lipoate
Thioctic acid
1,2-Dithiolane-3R-pentanoic acid

DATABASE IDS

CAS Number 62-46-4

PROPERTIES

Hydrophobicity(logP) 2.1
Solubility Insoluble

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical
Description A vitamin-like antioxidant. [PubChem]
Indication For nutritional supplementation, also for treating dietary shortage or imbalance.
Pharmacology Lipoic acid (or α-lipoic acid) is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Neither DMSA nor MSM can cross the blood-brain barrier, which is why both lipoic acid and DMSA are used. It is hypothesized that this treatment-along with carnitine, dimethylglycine (DMG), Vitamin B6, folic acid, and magnesium—could be used to treat autism and amalgam poisoning. In this hypothesis, the reason why autism is difficult to treat is that mercury is attached to the brain cells and most medicines and vitamin supplements do not penetrate the blood-brain barrier. However, α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.
Affected Organisms
Humans and other mammals
References
Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [Pubmed]
REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. [Pubmed]
External Links
Wikipedia

REFERENCES

  • Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. Pubmed
  • REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. Pubmed