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

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
Structure of THIOCTIC ACID MEGLUMINE

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

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 ( + / - )

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.

Approval Year

Conditions
PubMed

PubMed

TitleDatePubMed
Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions.
2000
Diabetes-induced changes in retinal NAD-redox status: pharmacological modulation and implications for pathogenesis of diabetic retinopathy.
2001
Effect of DL-alpha-lipoic acid on mitochondrial enzymes in aged rats.
2001 Nov 28
Antioxidants attenuate early up regulation of retinal vascular endothelial growth factor in streptozotocin-diabetic rats.
2001 Sep
Amelioration of docetaxel/cisplatin induced polyneuropathy by alpha-lipoic acid.
2003 Feb
The influence of lipoic acid on adriamycin-induced hyperlipidemic nephrotoxicity in rats.
2003 May
Melatonin, xanthurenic acid, resveratrol, EGCG, vitamin C and alpha-lipoic acid differentially reduce oxidative DNA damage induced by Fenton reagents: a study of their individual and synergistic actions.
2003 May
Plasma kinetics, metabolism, and urinary excretion of alpha-lipoic acid following oral administration in healthy volunteers.
2003 Nov
An alpha-lipoic acid-vitamin E mixture reduces post-embolism lipid peroxidation, cerebral infarction, and neurological deficit in rats.
2003 Oct
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
Protective effect of DL-alpha-lipoic acid in cyclophosphamide induced oxidative injury in rat testis.
2004 Dec
Oxidative stress and antioxidant supplementation in the management of diabetic cardiovascular disease.
2004 Jan
Oxidative stress and the use of antioxidants in diabetes: linking basic science to clinical practice.
2005 Apr 29
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
Syntheses of novel indole lipoic acid derivatives and their antioxidant effects on lipid peroxidation.
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
Oxidative stress and DNA single strand breaks in skeletal muscle of aged rats: role of carnitine and lipoicacid.
2006 Apr
Carnitine and lipoic acid alleviates protein oxidation in heart mitochondria during aging process.
2006 Apr
Salubrious effects of lipoic acid against adriamycin-induced clastogenesis and apoptosis in Wistar rat bone marrow cells.
2006 May 15
Protective role of eicosapentaenoate-lipoate (EPA-LA) derivative in combating oxidative hepatocellular injury in hypercholesterolemic atherogenesis.
2006 Nov
Insight into the role of DL-alpha-lipoic acid against cyclophosphamide induced alterations in calcium sensitivity of cardiac myofilaments.
2006 Sep
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
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 Sat Dec 16 08:13:49 GMT 2023
Edited
by admin
on Sat Dec 16 08:13:49 GMT 2023
Record UNII
146TUC9N9F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOCTIC ACID MEGLUMINE
Common Name English
1,2-DITHIOLANE-3-PENTANOIC ACID, COMPD. WITH 1-DEOXY-1-(METHYLAMINO)-D-GLUCITOL (1:1)
Common Name English
D-GLUCITOL, 1-DEOXY-1-(METHYLAMINO)-, 1,2-DITHIOLANE-3-PENTANOATE (1:1) (SALT)
Systematic Name English
.ALPHA.-LIPOIC ACID MEGLUMINE
Common Name English
ALPHA-LIPOIC ACID, MEGLUMINE SALT
Common Name English
Thioctic acid meglumine [WHO-DD]
Common Name English
.ALPHA.-LIPOIC ACID, MEGLUMINE SALT
Common Name English
Code System Code Type Description
PUBCHEM
91668164
Created by admin on Sat Dec 16 08:13:50 GMT 2023 , Edited by admin on Sat Dec 16 08:13:50 GMT 2023
PRIMARY
FDA UNII
146TUC9N9F
Created by admin on Sat Dec 16 08:13:50 GMT 2023 , Edited by admin on Sat Dec 16 08:13:50 GMT 2023
PRIMARY
CAS
176110-78-4
Created by admin on Sat Dec 16 08:13:50 GMT 2023 , Edited by admin on Sat Dec 16 08:13:50 GMT 2023
ALTERNATIVE
SMS_ID
100000144654
Created by admin on Sat Dec 16 08:13:50 GMT 2023 , Edited by admin on Sat Dec 16 08:13:50 GMT 2023
PRIMARY
EVMPD
SUB121426
Created by admin on Sat Dec 16 08:13:50 GMT 2023 , Edited by admin on Sat Dec 16 08:13:50 GMT 2023
PRIMARY
CAS
176110-77-3
Created by admin on Sat Dec 16 08:13:50 GMT 2023 , Edited by admin on Sat Dec 16 08:13:50 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY