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Details

Stereochemistry RACEMIC
Molecular Formula C8H15NOS2
Molecular Weight 205.341
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOCTIC ACID AMIDE

SMILES

NC(=O)CCCCC1CCSS1

InChI

InChIKey=FCCDDURTIIUXBY-UHFFFAOYSA-N
InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)

HIDE SMILES / InChI

Description
Curator's Comment: httpDescription was created based on several sources, including http://www.trc-canada.com/product-detail/?L468710 and https://www.ncbi.nlm.nih.gov/pubmed/11778851

Thioctic acid amide is a coenzyme, which transfer acetyl and hydrogen in pyruvate deacylation oxidation process, used for pharmaceuticals. Thioctic acid amide has been described as antioxidant, preventing oxidant-mediated apoptosis. It may be used in treatment of insulin resistance by stimulating mitochondrial biogenesis. When used in combination with Alprostadil, it has shown to have a good therapeutic effect on early diabetic nephropathy. Thioctic acid amide is an ingredient of Lipochol, used for prevention of liver diseases, hepatoprotection from drugs, autointoxication.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Preventing
Approved
8583
Lipochol

Approved Use

Prevention of liver diseases. Hepatoprotection from drugs, autointoxication
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6675 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11951812/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1793 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11951812/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.2 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18069903/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID, ( )- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4466 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11951812/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2621 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11951812/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.68 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18069903/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID, ( )- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11951812/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11951812/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
13.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18069903/
600 mg single, oral
dose: 600 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIOCTIC ACID, ( )- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
PubMed

PubMed

TitleDatePubMed
Phosphorylation of formate dehydrogenase in potato tuber mitochondria.
2003-07-11
Structural basis for flip-flop action of thiamin pyrophosphate-dependent enzymes revealed by human pyruvate dehydrogenase.
2003-06-06
MR diffusion imaging and MR spectroscopy of maple syrup urine disease during acute metabolic decompensation.
2003-06
Prevention of oxidant-induced cell death by lysosomotropic iron chelators.
2003-05-15
Differential effect of DCA treatment on the pyruvate dehydrogenase complex in patients with severe PDHC deficiency.
2003-05
Splicing error in E1alpha pyruvate dehydrogenase mRNA caused by novel intronic mutation responsible for lactic acidosis and mental retardation.
2003-04-04
Antisense inhibition of mitochondrial pyruvate dehydrogenase E1alpha subunit in anther tapetum causes male sterility.
2003-04
Identification of 36-kDa flagellar phosphoproteins associated with hamster sperm motility.
2003-03
2-Oxo acid dehydrogenase complexes in redox regulation.
2003-03
2-Oxo acid dehydrogenase complexes of multicellular organisms.
2003-03
Catalysis of diaphorase reactions by Mycobacterium tuberculosis lipoamide dehydrogenase occurs at the EH4 level.
2003-02-25
Selenite sensitizes mitochondrial permeability transition pore opening in vitro and in vivo: a possible mechanism for chemo-protection.
2003-02-15
A new case of pyruvate dehydrogenase deficiency due to a novel mutation in the PDX1 gene.
2003-02
Encapsulation of an 86-kDa assembly intermediate inside the cavities of GroEL and its single-ring variant SR1 by GroES.
2003-01-24
Histidine 407, a phantom residue in the E1 subunit of the Escherichia coli pyruvate dehydrogenase complex, activates reductive acetylation of lipoamide on the E2 subunit. An explanation for conservation of active sites between the E1 subunit and transketolase.
2002-12-31
The lipoamide dehydrogenase from Mycobacterium tuberculosis permits the direct observation of flavin intermediates in catalysis.
2002-12-10
Clofibric acid stimulates branched-chain amino acid catabolism by three mechanisms.
2002-11-15
Elongation factor Tu and E1 beta subunit of pyruvate dehydrogenase complex act as fibronectin binding proteins in Mycoplasma pneumoniae.
2002-11
Folding kinetics of the lipoic acid-bearing domain of human mitochondrial branched chain alpha-ketoacid dehydrogenase complex.
2002-10-23
Inactivation of the 2-oxo acid dehydrogenase complexes upon generation of intrinsic radical species.
2002-10
Insulin increases branched-chain alpha-ketoacid dehydrogenase kinase expression in Clone 9 rat cells.
2002-10
Tissue-specific effects of chronic dietary leucine and norleucine supplementation on protein synthesis in rats.
2002-10
Diagnosis and molecular analysis of three male patients with thiamine-responsive pyruvate dehydrogenase complex deficiency.
2002-09-15
Gene therapy for pyruvate dehydrogenase E1alpha deficiency using recombinant adeno-associated virus 2 (rAAV2) vectors.
2002-09
Glutaredoxins catalyze the reduction of glutathione by dihydrolipoamide with high efficiency.
2002-08-02
A novel Y243S mutation in the pyruvate dehydrogenase El alpha gene subunit: correlation with thiamine pyrophosphate interaction.
2002-08
Detection of pyruvate dehydrogenase E1 alpha-subunit deficiencies in females by immunohistochemical demonstration of mosaicism in cultured fibroblasts.
2002-07
Interchangeable enzyme modules. Functional replacement of the essential linker of the biotinylated subunit of acetyl-CoA carboxylase with a linker from the lipoylated subunit of pyruvate dehydrogenase.
2002-06-21
Diagnosis and treatment of maple syrup disease: a study of 36 patients.
2002-06
Primary biliary cirrhosis: seeking the silent partner of autoimmunity.
2002-06
Solution structure and dynamics of the lipoic acid-bearing domain of human mitochondrial branched-chain alpha-keto acid dehydrogenase complex.
2002-05-03
Maple syrup urine disease: mutation analysis in Turkish patients.
2002-05
The E1beta and E2 subunits of the Bacillus subtilis pyruvate dehydrogenase complex are involved in regulation of sporulation.
2002-05
Two-photon fluorescence spectroscopy and microscopy of NAD(P)H and flavoprotein.
2002-05
Recurrent intragenomic recombination leading to sequence homogenization during the evolution of the lipoyl-binding domain.
2002-04-09
Cerebral white matter involvement in children with mitochondrial encephalopathies.
2002-04
Substrate channelling in 2-oxo acid dehydrogenase multienzyme complexes.
2002-04
[Maple syrup urine disease].
2002-04
[Pyruvate dehydrogenase complex deficiency].
2002-04
Glucose-stimulated insulin secretion does not require activation of pyruvate dehydrogenase: impact of adenovirus-mediated overexpression of PDH kinase and PDH phosphate phosphatase in pancreatic islets.
2002-03-08
Out of Africa again and again.
2002-03-07
Clinical significance of positive immunoblotting but negative immunofluorescence for antimitochondrial antibodies in patients with liver diseases other than primary biliary cirrhosis.
2002-03
Activation of the promoters of Arabidopsis genes for the branched-chain alpha-keto acid dehydrogenase complex in transgenic tobacco BY-2 cells under sugar starvation.
2002-03
Structural basis of the dysfunctioning of human 2-oxo acid dehydrogenase complexes.
2002-02
Pyruvate dehydrogenase E3 binding protein deficiency.
2002-02
Atrophic corpus gastritis and Helicobacter pylori infection in primary biliary cirrhosis.
2002-01
[Inherited metabolic diseases associated with West syndrome].
2002
The complex fate of alpha-ketoacids.
2002
Primary biliary cirrhosis: lessons learned from an organ-specific disease.
2001-12
Gender-specific occurrence of West syndrome in patients with pyruvate dehydrogenase complex deficiency.
2001-12
Patents

Patents

20020049176
1
JPS62175417A
1

Sample Use Guides

In Vivo Use Guide
2 tab once daily. Should be taken with food: Take after meals. Lipochol consists of Thioctamide (Thioctic acid amide) 3.5 mg, inositol 30 mg, Ca pantothenate 5 mg, orotic acid 30 mg, methionine 50 mg, nicotinamide 10 mg, vit B1 2 mg, vit B2 1 mg, vit B6 1 mg, vit B12 1 mcg, vit C 30 mg
Route of Administration: Oral
In Vitro Use Guide
Thioctic acid amide concentrations ≤200 uM lessened or almost totally prevented lysosomal membrane destabilization, while concentrations >200 uM had toxic effects on murine macrophage-like J774 cells
Name Type Language
THIOCTAMIDE
WHO-DD  
Preferred Name English
THIOCTIC ACID AMIDE
JAN  
Common Name English
LIPAMIDE
Common Name English
DL-.ALPHA.-LIPOIC ACID AMIDE
Common Name English
1,2-DITHIOLANE-3-PENTANAMIDE
Systematic Name English
NSC-759236
Code English
Thioctamide [WHO-DD]
Common Name English
.ALPHA.-LIPAMIDE
Common Name English
(±)-1,2-DITHIOLANE-3-PENTANAMIDE
Systematic Name English
(±)-THIOCTIC ACID AMIDE
Common Name English
LIPOAMIDE
Common Name English
LIPOAMID
Common Name English
5-(1,2-DITHIOLAN-3-YL)VALERAMIDE
Systematic Name English
DL-6,8-THIOCTAMIDE
Common Name English
LIPOICIN
Common Name English
5-(1,2-DITHIOLAN-3-YL)PENTANAMIDE
Systematic Name English
LIPOACIN
Common Name English
DL-LIPOAMIDE
Common Name English
THIOCTIC ACID AMIDE [JAN]
Common Name English
NSC-90787
Code English
1,2-DITHIOLANE-3-VALERAMIDE
Systematic Name English
(±)-1,2-DITHIOLANE-3-VALERAMIDE
Systematic Name English
PATHOCLON
Brand Name English
Code System Code Type Description
ECHA (EC/EINECS)
213-375-2
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
WIKIPEDIA
LIPOAMIDE
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
EVMPD
SUB15535MIG
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
FDA UNII
Q1GT04827L
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
RXCUI
1597391
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY RxNorm
SMS_ID
100000077015
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
NSC
90787
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID2046541
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
EVMPD
SUB33443
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL1403899
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
CAS
940-69-2
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
CHEBI
17460
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
NSC
759236
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
PUBCHEM
863
Created by admin on Mon Mar 31 21:34:05 GMT 2025 , Edited by admin on Mon Mar 31 21:34:05 GMT 2025
PRIMARY
SUBSTANCE RECORD
Structure of THIOCTIC ACID AMIDE
NIH
NCATS
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