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

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
Structure of ALPHA LIPOIC ACID

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)

HIDE SMILES / InChI

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 ( + / - )

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.

Approval Year

Conditions
PubMed

PubMed

TitleDatePubMed
Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase.
1951 Jul 27
Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers.
2003 Nov
Alpha-lipoic acid treatment prevents the diabetes-induced attenuation of the afferent limb of the baroreceptor reflex in rats.
2003 Oct 31
Effect of DL-alpha-lipoic acid on the status of lipid peroxidation and lipids in aged rats.
2003 Sep
[Toxicological aspects and health risks associated with hydroquinone in skin bleaching formula].
2004 Apr 17
Effect of antioxidants and ACE inhibition on chemical modification of proteins and progression of nephropathy in the streptozotocin diabetic rat.
2004 Aug
Remedial effect of DL-alpha-lipoic acid against adriamycin induced testicular lipid peroxidation.
2004 Dec
Protective effect of DL-alpha-lipoic acid in cyclophosphamide induced oxidative injury in rat testis.
2004 Dec
Protective effect of DL-alpha-lipoic acid on cyclophosphamide induced oxidative cardiac injury.
2004 Dec 30
Development of a sustained release dosage form for alpha-lipoic acid. II. Evaluation in human volunteers.
2004 Jan
Oxidative stress and antioxidant supplementation in the management of diabetic cardiovascular disease.
2004 Jan
Burning Mouth Syndrome: open trial of psychotherapy alone, medication with alpha-lipoic acid (thioctic acid), and combination therapy.
2004 Jan-Feb
alpha-lipoic acid inhibits endotoxin-stimulated expression of iNOS and nitric oxide independent of the heat shock response in RAW 264.7 cells.
2004 Jul
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
Attenuation of chloroquine-induced renal damage by alpha-lipoic acid: possible antioxidant mechanism.
2004 Sep
Conformational stability and thermodynamic characterization of the lipoic acid bearing domain of human mitochondrial branched chain alpha-ketoacid dehydrogenase.
2004 Sep
Mitigation of oxidative stress in cyclophosphamide-challenged hepatic tissue by DL-alpha-lipoic acid.
2005 Apr
Oxidative stress and the use of antioxidants in diabetes: linking basic science to clinical practice.
2005 Apr 29
The protective role of DL-alpha-lipoic acid in biogenic amines catabolism triggered by Abeta amyloid vaccination in mice.
2005 Apr 30
Cytoprotective role of DL-alpha-lipoic acid in cyclophosphamide induced myocardial toxicity.
2005 Aug
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
The protective role of DL-alpha-lipoic acid in the oxidative vulnerability triggered by Abeta-amyloid vaccination in mice.
2005 Feb
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
Arsenic intoxication-induced reduction of glutathione level and of the activity of related enzymes in rat brain regions: reversal by DL-alpha-lipoic acid.
2005 Mar
Syntheses of novel indole lipoic acid derivatives and their antioxidant effects on lipid peroxidation.
2005 Mar
Pharmacokinetics of alpha-lipoic acid in subjects with severe kidney damage and end-stage renal disease.
2005 Mar
Evidence for a non-antioxidant, dose-dependent role of alpha -lipoic acid in caspase-3 and ERK2 activation in endothelial cells.
2005 May
Arsenic trioxide (As(2)O(3)) induces apoptosis through activation of Bax in hematopoietic cells.
2005 May 5
dl-alpha-lipoic acid ameliorates cyclophosphamide induced cardiac mitochondrial injury.
2005 Nov 5
Decrease in NADPH-cytochrome P450 reductase activity of the human heart, Liver and lungs in the presence of alpha-lipoic acid.
2006
[Oxaliplatin neurotoxicity].
2006 Feb 1
Effect of alpha-lipoic acid supplementation on markers of protein oxidation in post-mitotic tissues of ageing rat.
2006 Jan-Feb
Contact dermatitis to alpha-lipoic acid in an anti-wrinkle cream.
2006 Jul
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
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
Protective efficacy of alpha-lipoic acid on acetylcholinesterase activity in aged rat brain regions.
2006 Summer
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
Adjunctive care with nutritional, herbal, and homeopathic complementary and alternative medicine modalities in stroke treatment and rehabilitation.
2007 Jul-Aug
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
Patents

Sample Use Guides

Recommended oral therapeutic dosages of alpha-lipoic acid range from 600-1800 mg daily.
Route of Administration: Oral
In Vitro Use Guide
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 Fri Dec 15 14:59:17 UTC 2023
Edited
by admin
on Fri Dec 15 14:59:17 UTC 2023
Record UNII
73Y7P0K73Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
.ALPHA.-LIPOIC ACID
Preferred Name English
ALPHA LIPOIC ACID
USP   USP-RS   VANDF  
USP  
Official Name English
THIOCTIC ACID
EP   HSDB   INCI   JAN   MART.   WHO-DD  
INCI  
Preferred Name English
THIOCTIC ACID [INCI]
Common Name English
DL-6,8-THIOCTIC ACID
Common Name English
ALPHA LIPOIC ACID [VANDF]
Common Name English
NSC-90788
Code English
BILETAN
Brand Name English
ALPHA-LIPOIC ACID
VANDF  
Common Name English
THIOCTIC ACID DL-FORM [MI]
Common Name English
THIOCTIC ACID, (±)-
Common Name English
NSC-628502
Code English
ACIDUM THIOCTICUM
Common Name English
6,8-THIOCTIC ACID
Common Name English
THIOCACID
Brand Name English
Thioctic acid [WHO-DD]
Common Name English
1,2-DITHIOLANE-3-PENTANOIC ACID
Systematic Name English
ALPHA-LIPOIC ACID [VANDF]
Common Name English
THIOCTIC ACID [MART.]
Common Name English
THIOCTIC ACID [JAN]
Common Name English
A-LIPOICUM ACIDUM
HPUS  
Common Name English
TIOCTIC ACID
Common Name English
LIPOIC ACID, DL-
Common Name English
THIOCTIC ACID [HSDB]
Common Name English
.DELTA.-(3-(1,2-DITHIACYCLOPENTYL))PENTANOIC ACID
Common Name English
ALPHA LIPOIC ACID [USP IMPURITY]
Common Name English
THIOCTIC ACID [MI]
Common Name English
THIOCTIC ACID [EP MONOGRAPH]
Common Name English
5-(3-(1,2-DITHIOLANYL))PENTANOIC ACID
Common Name English
A-LIPOICUM ACIDUM [HPUS]
Common Name English
ALPHA LIPOIC ACID [USP-RS]
Common Name English
.ALPHA.-LIPOIC ACID, (±)-
Common Name English
THIOCTATE
Common Name English
5-(1,2-DITHIOLAN-3-YL)VALERIC ACID
Systematic Name English
1,2-DITHIOLANE-3-VALERIC ACID
Systematic Name English
5-((3RS)-1,2-DITHIOLAN-3-YL)PENTANOIC ACID
Systematic Name English
THIOCTAN
Brand Name English
Classification Tree Code System Code
WHO-VATC QA16AX01
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
EU-Orphan Drug EU/3/16/1646
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
DSLD 8 (Number of products:2523)
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
WHO-ATC A16AX01
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
Code System Code Type Description
CAS
1077-28-7
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-534-6
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
ALTERNATIVE
CHEBI
30314
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
FDA UNII
73Y7P0K73Y
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
MESH
D008063
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
RXCUI
6417
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
PUBCHEM
864
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
MERCK INDEX
m10749
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY Merck Index
SMS_ID
100000086014
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
CHEBI
30313
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
CHEBI
16494
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
DRUG CENTRAL
4732
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
214-071-2
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
NSC
628502
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
CAS
62-46-4
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID7025508
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
DAILYMED
73Y7P0K73Y
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
RS_ITEM_NUM
1368201
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL33864
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
EVMPD
SUB15537MIG
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
RXCUI
618060
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
ALTERNATIVE
NCI_THESAURUS
C61595
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
NSC
90788
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
HSDB
7818
Created by admin on Fri Dec 15 14:59:17 UTC 2023 , Edited by admin on Fri Dec 15 14:59:17 UTC 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
ENANTIOMER -> RACEMATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY