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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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.6 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
5.6 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.5 h
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

Doses

DosePopulationAdverse 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...
Other AEs:
Itching (0.8%)
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:
Disc. AE: Skin eruption...
AEs leading to
discontinuation/dose reduction:
Skin eruption (10%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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]
no
no
no
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
yes
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets
PubMed

PubMed

TitleDatePubMed
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
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 Mon Mar 31 21:56:55 GMT 2025
Edited
by admin
on Mon Mar 31 21:56:55 GMT 2025
Record UNII
146TUC9N9F
Record Status Validated (UNII)
Record Version
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Name Type Language
THIOCTIC ACID MEGLUMINE
Common Name English
.ALPHA.-LIPOIC ACID MEGLUMINE
Preferred 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 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 Mon Mar 31 21:56:55 GMT 2025 , Edited by admin on Mon Mar 31 21:56:55 GMT 2025
PRIMARY
FDA UNII
146TUC9N9F
Created by admin on Mon Mar 31 21:56:55 GMT 2025 , Edited by admin on Mon Mar 31 21:56:55 GMT 2025
PRIMARY
CAS
176110-78-4
Created by admin on Mon Mar 31 21:56:55 GMT 2025 , Edited by admin on Mon Mar 31 21:56:55 GMT 2025
ALTERNATIVE
SMS_ID
100000144654
Created by admin on Mon Mar 31 21:56:55 GMT 2025 , Edited by admin on Mon Mar 31 21:56:55 GMT 2025
PRIMARY
EVMPD
SUB121426
Created by admin on Mon Mar 31 21:56:55 GMT 2025 , Edited by admin on Mon Mar 31 21:56:55 GMT 2025
PRIMARY
CAS
176110-77-3
Created by admin on Mon Mar 31 21:56:55 GMT 2025 , Edited by admin on Mon Mar 31 21:56:55 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY