Details
Stereochemistry | EPIMERIC |
Molecular Formula | C8H14O2S2.C7H17NO5 |
Molecular Weight | 401.539 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CCCCC1CCSS1.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
InChI
InChIKey=QPTVXUUGWBDFLV-WZTVWXICSA-N
InChI=1S/C8H14O2S2.C7H17NO5/c9-8(10)4-2-1-3-7-5-6-11-12-7;1-8-2-4(10)6(12)7(13)5(11)3-9/h7H,1-6H2,(H,9,10);4-13H,2-3H2,1H3/t;4-,5+,6+,7+/m.0/s1
Molecular Formula | C8H14O2S2 |
Molecular Weight | 206.326 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | C7H17NO5 |
Molecular Weight | 195.2136 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30241687/ |
600 mg 1 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
THIOCTIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30241687/ |
600 mg 1 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
THIOCTIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30241687/ |
600 mg 1 times / day steady-state, oral dose: 600 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
THIOCTIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg 1 times / day multiple, oral Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Disc. AE: Gastrointestinal disturbance... AEs leading to discontinuation/dose reduction: Gastrointestinal disturbance (8.2%) Sources: |
600 mg 3 times / day multiple, oral Recommended Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Other AEs: Itching... |
600 mg 3 times / day multiple, oral Recommended Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Disc. AE: Skin eruption... AEs leading to discontinuation/dose reduction: Skin eruption (10%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Gastrointestinal disturbance | 8.2% Disc. AE |
600 mg 1 times / day multiple, oral Recommended Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Itching | 0.8% | 600 mg 3 times / day multiple, oral Recommended Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Skin eruption | 10% Disc. AE |
600 mg 3 times / day multiple, oral Recommended Dose: 600 mg, 3 times / day Route: oral Route: multiple Dose: 600 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >1000 uM] | ||||
Page: 69.0 |
no | |||
Page: 346.0 |
no | |||
Page: 71.0 |
no | |||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/23984871/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/23984871/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 448 | 449 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. | 1951 Jul 27 |
|
Human placental Na+-dependent multivitamin transporter. Cloning, functional expression, gene structure, and chromosomal localization. | 1999 May 21 |
|
Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. | 2000 |
|
The antioxidant effect of DL-alpha-lipoic acid on copper-induced acute hepatitis in Long-Evans Cinnamon (LEC) rats. | 2001 Jan |
|
New metabolic pathways of alpha-lipoic acid. | 2001 Jun |
|
Antioxidants attenuate early up regulation of retinal vascular endothelial growth factor in streptozotocin-diabetic rats. | 2001 Sep |
|
Lipoic acid in combination with a chelator ameliorates lead-induced peroxidative damages in rat kidney. | 2002 Aug |
|
The neuroprotective antioxidant alpha-lipoic acid induces detoxication enzymes in cultured astroglial cells. | 2002 Jun |
|
Burning mouth syndrome (BMS): double blind controlled study of alpha-lipoic acid (thioctic acid) therapy. | 2002 May |
|
Combined efficacies of lipoic acid and meso-2,3-dimercaptosuccinic acid on lead-induced erythrocyte membrane lipid peroxidation and antioxidant status in rats. | 2003 Apr |
|
Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers. | 2003 Nov |
|
Effect of antioxidants and ACE inhibition on chemical modification of proteins and progression of nephropathy in the streptozotocin diabetic rat. | 2004 Aug |
|
L-carnitine and DL-alpha-lipoic acid reverse the age-related deficit in glutathione redox state in skeletal muscle and heart tissues. | 2004 Jul |
|
Alpha-lipoic acid increases Na+K+ATPase activity and reduces lipofuscin accumulation in discrete brain regions of aged rats. | 2004 Jun |
|
[Effects of DL-alpha-lipoic acid on the experimentally induced diabetic cataract in rats]. | 2004 Mar |
|
Synthesis and characterization of new and potent alpha-lipoic acid derivatives. | 2004 Mar 1 |
|
Peroxide-mediated desulfurization of phosphorothioate oligonucleotides and its prevention. | 2005 Feb |
|
Beneficial effects of DL-alpha-lipoic acid on cyclophosphamide-induced oxidative stress in mitochondrial fractions of rat testis. | 2005 Feb 28 |
|
Protein oxidative damage in arsenic induced rat brain: influence of DL-alpha-lipoic acid. | 2005 Jan 15 |
|
Syntheses of novel indole lipoic acid derivatives and their antioxidant effects on lipid peroxidation. | 2005 Mar |
|
(R)-alpha-lipoic acid protects retinal pigment epithelial cells from oxidative damage. | 2005 Nov |
|
Decrease in NADPH-cytochrome P450 reductase activity of the human heart, Liver and lungs in the presence of alpha-lipoic acid. | 2006 |
|
Oxidative stress-mediated macromolecular damage and dwindle in antioxidant status in aged rat brain regions: role of L-carnitine and DL-alpha-lipoic acid. | 2006 Jun |
|
MafA expression and insulin promoter activity are induced by nicotinamide and related compounds in INS-1 pancreatic beta-cells. | 2006 Mar |
|
Modulatory role of lipoic acid on adriamycin-induced testicular injury. | 2006 Mar 25 |
|
Interfacial pH and surface pKa of a thioctic acid self-assembled monolayer. | 2006 Nov 7 |
|
Doxorubicin-induced reactive oxygen species generation and intracellular Ca2+ increase are reciprocally modulated in rat cardiomyocytes. | 2006 Oct 31 |
|
Application of N-PLS calibration to the simultaneous determination of Cu(2+), Cd(2+) and Pb(2+) using peptide modified electrochemical sensors. | 2006 Sep |
|
Insight into the role of DL-alpha-lipoic acid against cyclophosphamide induced alterations in calcium sensitivity of cardiac myofilaments. | 2006 Sep |
|
Diabetic painful neuropathy: current and future treatment options. | 2007 |
|
Modulation of p38 mitogen-activated protein kinase cascade and metalloproteinase activity in diaphragm muscle in response to free radical scavenger administration in dystrophin-deficient Mdx mice. | 2007 Feb |
|
Monolayer-protected gold nanoparticles by the self-assembly of micellar poly(ethylene oxide)-b-poly(epsilon-caprolactone) block copolymer. | 2007 Feb 13 |
|
Acrolein, a toxicant in cigarette smoke, causes oxidative damage and mitochondrial dysfunction in RPE cells: protection by (R)-alpha-lipoic acid. | 2007 Jan |
|
Zinc and the cytoskeleton in the neuronal modulation of transcription factor NFAT. | 2007 Jan |
|
CoCl2 induces protective events via the p38-MAPK signalling pathway and ANP in the perfused amphibian heart. | 2007 Jul |
|
Beneficial effect of DL-alpha-lipoic acid on cyclosporine A induced hyperlipidemic nephropathy in rats. | 2007 Jul |
|
Adjunctive care with nutritional, herbal, and homeopathic complementary and alternative medicine modalities in stroke treatment and rehabilitation. | 2007 Jul-Aug |
|
Unusual fluorescence enhancement of a novel carbazolyldiacetylene bound to gold nanoparticles. | 2007 Jun 5 |
|
Effect of DL-alpha-lipoic acid on cyclophosphamide induced lysosomal changes in oxidative cardiotoxicity. | 2007 May 1 |
|
Efficacy of DL-alpha-lipoic acid on methanol induced free radical changes, protein oxidative damages and hsp70 expression in folate deficient rat nervous tissue. | 2007 May 1 |
|
Therapeutic efficacy of DL-alpha-lipoic acid on cyclosporine A induced renal alterations. | 2007 Oct 1 |
|
Potent upregulation of glutathione and NAD(P)H:quinone oxidoreductase 1 by alpha-lipoic acid in human neuroblastoma SH-SY5Y cells: protection against neurotoxicant-elicited cytotoxicity. | 2008 May |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:56:55 GMT 2025
by
admin
on
Mon Mar 31 21:56:55 GMT 2025
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Record UNII |
146TUC9N9F
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Record Status |
Validated (UNII)
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Record Version |
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91668164
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146TUC9N9F
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176110-78-4
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100000144654
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SUB121426
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176110-77-3
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