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
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
Remedial effect of DL-alpha-lipoic acid against adriamycin induced testicular lipid peroxidation.
2004 Dec
Protective effect of DL-alpha-lipoic acid on cyclophosphamide induced oxidative cardiac injury.
2004 Dec 30
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
Attenuation of serum lipid abnormalities and cardiac oxidative stress by eicosapentaenoate-lipoate (EPA-LA) derivative in experimental hypercholesterolemia.
2005 May
Oxidative stress on mitochondrial antioxidant defense system in the aging process: role of DL-alpha-lipoic acid and L-carnitine.
2005 May
Brain regional responses in antioxidant system to alpha-lipoic acid in arsenic intoxicated rat.
2005 May 15
Arsenic trioxide (As(2)O(3)) induces apoptosis through activation of Bax in hematopoietic cells.
2005 May 5
(R)-alpha-lipoic acid protects retinal pigment epithelial cells from oxidative damage.
2005 Nov
Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways.
2005 Nov
Protective effects of different antioxidants and amrinone on vancomycin-induced nephrotoxicity.
2005 Nov
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
Oxidative stress and DNA single strand breaks in skeletal muscle of aged rats: role of carnitine and lipoicacid.
2006 Apr
RS-alpha-lipoic acid protects cholinergic cells against sodium nitroprusside and amyloid-beta neurotoxicity through restoration of acetyl-CoA level.
2006 Aug
Protective effect of DL-alpha-lipoic acid on cyclophosphamide induced hyperlipidemic cardiomyopathy.
2006 Aug 14
Reactive oxygen species mediate caspase activation and apoptosis induced by lipoic acid in human lung epithelial cancer cells through Bcl-2 down-regulation.
2006 Dec
[Oxaliplatin neurotoxicity].
2006 Feb 1
Contact dermatitis to alpha-lipoic acid in an anti-wrinkle cream.
2006 Jul
Antioxidants reduce cone cell death in a model of retinitis pigmentosa.
2006 Jul 25
Modulatory role of lipoic acid on adriamycin-induced testicular injury.
2006 Mar 25
A phase II study with antioxidants, both in the diet and supplemented, pharmaconutritional support, progestagen, and anti-cyclooxygenase-2 showing efficacy and safety in patients with cancer-related anorexia/cachexia and oxidative stress.
2006 May
Salubrious effects of lipoic acid against adriamycin-induced clastogenesis and apoptosis in Wistar rat bone marrow cells.
2006 May 15
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
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.
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 Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
EU-Orphan Drug EU/3/16/1646
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
DSLD 8 (Number of products:2523)
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
WHO-ATC A16AX01
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
Code System Code Type Description
CAS
1077-28-7
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-534-6
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
ALTERNATIVE
CHEBI
30314
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
FDA UNII
73Y7P0K73Y
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
MESH
D008063
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
RXCUI
6417
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
PUBCHEM
864
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
MERCK INDEX
M10749
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY Merck Index
SMS_ID
100000086014
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
CHEBI
30313
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
CHEBI
16494
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
DRUG CENTRAL
4732
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
214-071-2
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
NSC
628502
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
CAS
62-46-4
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
SUPERSEDED
EPA CompTox
DTXSID7025508
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
DAILYMED
73Y7P0K73Y
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
RS_ITEM_NUM
1368201
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
ChEMBL
CHEMBL33864
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
EVMPD
SUB15537MIG
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
RXCUI
618060
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
ALTERNATIVE
NCI_THESAURUS
C61595
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
NSC
90788
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY
HSDB
7818
Created by admin on Wed Jul 05 22:31:19 UTC 2023 , Edited by admin on Wed Jul 05 22:31:19 UTC 2023
PRIMARY