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
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
| 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.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of DL-alpha-lipoic acid on glutathione metabolic enzymes in aged rats. | 2001 Dec |
|
| New metabolic pathways of alpha-lipoic acid. | 2001 Jun |
|
| Glutathione and alpha-lipoate in diabetic rats: nerve function, blood flow and oxidative state. | 2001 May |
|
| Effect of DL-alpha-lipoic acid on mitochondrial enzymes in aged rats. | 2001 Nov 28 |
|
| Alpha-lipoic acid protects rat cortical neurons against cell death induced by amyloid and hydrogen peroxide through the Akt signalling pathway. | 2001 Oct 26 |
|
| Antioxidants attenuate early up regulation of retinal vascular endothelial growth factor in streptozotocin-diabetic rats. | 2001 Sep |
|
| alpha-Lipoic acid prevents the development of glucose-induced insulin resistance in 3T3-L1 adipocytes and accelerates the decline in immunoreactive insulin during cell incubation. | 2001 Sep |
|
| 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 |
|
| The influence of lipoic acid on adriamycin-induced hyperlipidemic nephrotoxicity in rats. | 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 |
|
| Effect of antioxidants and ACE inhibition on chemical modification of proteins and progression of nephropathy in the streptozotocin diabetic rat. | 2004 Aug |
|
| Development of a sustained release dosage form for alpha-lipoic acid. II. Evaluation in human volunteers. | 2004 Jan |
|
| [Effects of DL-alpha-lipoic acid on the experimentally induced diabetic cataract in rats]. | 2004 Mar |
|
| 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 |
|
| 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 |
|
| dl-alpha-lipoic acid ameliorates cyclophosphamide induced cardiac mitochondrial injury. | 2005 Nov 5 |
|
| 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 |
|
| Protective effect of DL-alpha-lipoic acid on cyclophosphamide induced hyperlipidemic cardiomyopathy. | 2006 Aug 14 |
|
| Protective effect of lipoic acid on micronuclei induction by cyclophosphamide. | 2006 Feb |
|
| Protective role of eicosapentaenoate-lipoate (EPA-LA) derivative in combating oxidative hepatocellular injury in hypercholesterolemic atherogenesis. | 2006 Nov |
|
| Diabetic painful neuropathy: current and future treatment options. | 2007 |
|
| Beneficial effect of DL-alpha-lipoic acid on cyclosporine A induced hyperlipidemic nephropathy in rats. | 2007 Jul |
|
| 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 |
Sample Use Guides
Recommended oral therapeutic dosages of
alpha-lipoic acid range from 600-1800 mg daily.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:13:49 GMT 2023
by
admin
on
Sat Dec 16 08:13:49 GMT 2023
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| Record UNII |
146TUC9N9F
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| Record Status |
Validated (UNII)
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ACTIVE MOIETY |