Details
Stereochemistry | RACEMIC |
Molecular Formula | C8H14O2S2 |
Molecular Weight | 206.326 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCCCC1CCSS1
InChI
InChIKey=AGBQKNBQESQNJD-UHFFFAOYSA-N
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)
Thioctic acid also known as alpha-lipoic acid is a dietary supplement, which is a common ingredient in OTC (over-the-counter) multivitamin formulas and anti-aging supplements. Thioctic acid exists in both R- and S-enantiomeric forms, however, only R-form is essential as a cofactor in biological systems (the acid is coupled via an amide linkage to a lysine of several multienzyme complexes, such as the pyruvate dehydrogenase complex, the alpha-ketoglutarate dehydrogenase complex, the glycine cleavage system and the branched-chain oxo acid dehydrogenase complex). Most commercially available thioctic acid supplements are a mixture of both R and S enantiomers or R-form alone. Several studies have shown that the acid has beneficial effect on diabetes complications, cancer, glaucome, liver disease, etc. The mechanisms of thioctic acid is related to its antioxidant properties, metal chelator properties, however, those mechanisms need futher confirmation.
CNS Activity
Originator
Approval Year
PubMed
Title | Date | PubMed |
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Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. | 1951 Jul 27 |
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Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. | 2000 |
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Lipoic acid in combination with a chelator ameliorates lead-induced peroxidative damages in rat kidney. | 2002 Aug |
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Burning mouth syndrome (BMS): an open trial of comparative efficacy of alpha-lipoic acid (thioctic acid) with other therapies. | 2002 Sep |
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Early oxidative stress in the diabetic kidney: effect of DL-alpha-lipoic acid. | 2003 Jan 15 |
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Effect of antioxidants and ACE inhibition on chemical modification of proteins and progression of nephropathy in the streptozotocin diabetic rat. | 2004 Aug |
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Protective effect of DL-alpha-lipoic acid in cyclophosphamide induced oxidative injury in rat testis. | 2004 Dec |
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Burning Mouth Syndrome: open trial of psychotherapy alone, medication with alpha-lipoic acid (thioctic acid), and combination therapy. | 2004 Jan-Feb |
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Conformational stability and thermodynamic characterization of the lipoic acid bearing domain of human mitochondrial branched chain alpha-ketoacid dehydrogenase. | 2004 Sep |
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The protective role of DL-alpha-lipoic acid in biogenic amines catabolism triggered by Abeta amyloid vaccination in mice. | 2005 Apr 30 |
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Combined efficacies of DL-alpha-lipoic acid and meso 2,3 dimercaptosuccinic acid against arsenic induced toxicity in antioxidant systems of rats. | 2005 Dec 30 |
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Beneficial effects of DL-alpha-lipoic acid on cyclophosphamide-induced oxidative stress in mitochondrial fractions of rat testis. | 2005 Feb 28 |
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Syntheses of novel indole lipoic acid derivatives and their antioxidant effects on lipid peroxidation. | 2005 Mar |
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Oxidative stress on mitochondrial antioxidant defense system in the aging process: role of DL-alpha-lipoic acid and L-carnitine. | 2005 May |
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dl-alpha-lipoic acid ameliorates cyclophosphamide induced cardiac mitochondrial injury. | 2005 Nov 5 |
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Carnitine and lipoic acid alleviates protein oxidation in heart mitochondria during aging process. | 2006 Apr |
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[Oxaliplatin neurotoxicity]. | 2006 Feb 1 |
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Antioxidants reduce cone cell death in a model of retinitis pigmentosa. | 2006 Jul 25 |
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Salubrious effects of lipoic acid against adriamycin-induced clastogenesis and apoptosis in Wistar rat bone marrow cells. | 2006 May 15 |
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Doxorubicin-induced reactive oxygen species generation and intracellular Ca2+ increase are reciprocally modulated in rat cardiomyocytes. | 2006 Oct 31 |
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Acrolein, a toxicant in cigarette smoke, causes oxidative damage and mitochondrial dysfunction in RPE cells: protection by (R)-alpha-lipoic acid. | 2007 Jan |
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Zinc and the cytoskeleton in the neuronal modulation of transcription factor NFAT. | 2007 Jan |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.altmedrev.com/publications/11/3/232.pdf
Recommended oral therapeutic dosages of
alpha-lipoic acid range from 600-1800 mg daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9573120
Supplementation of Human Umbilical Vein Endothelial Cells with 100, 200, or 500 uM thioctic acid after inoculation with R. rickettsii restored the intracellular levels of thiols and glutathione peroxidase and reduced the intracellular peroxide levels in infected cells.
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QA16AX01
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EU-Orphan Drug |
EU/3/16/1646
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DSLD |
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WHO-ATC |
A16AX01
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)