Identification

Name
Lipoic Acid
Accession Number
DB00166  (NUTR00035)
Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Description

A vitamin-like antioxidant.

Structure
Thumb
Synonyms
  • (+)-alpha-Lipoic acid
  • (R)-(+)-Lipoate
  • (R)-(+)-lipoic acid
  • (R)-1,2-Dithiolane-3-pentanoic acid
  • (R)-1,2-dithiolane-3-valeric acid
  • (R)-6,8-thioctic acid
  • (R)-lipoic acid
  • Alpha lipoic acid
  • alpha-Lipoic acid
  • alpha-Liponsäure
  • D-thioctic acid
  • R-(+)-thioctic acid
  • R-alpha-lipoic acid
  • Thioctic acid
  • Thioctic acid D-form
  • α-lipoic acid
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
NoxicareLipoic Acid (10 mL/100mL) + Ginger oil (10 mL/100mL) + Indian frankincense (10 mL/100mL) + Ocimum tenuiflorum top (10 mL/100mL) + Rosemary oil (10 mL/100mL) + Turmeric oil (10 mL/100mL) + Willow bark (10 mL/100mL)CreamTopicalTruceuticals, Llc2010-03-012010-07-10Us
Tru-micinLipoic Acid (0.01 g/100mL) + Ginger (0.01 g/100mL) + Indian frankincense (0.01 g/100mL) + Ocimum tenuiflorum top (0.01 g/100mL) + Rosemary (0.01 g/100mL) + Salix alba bark (0.01 g/100mL) + Turmeric (0.01 g/100mL)LotionTopicalDispensing Solutions, Inc.2011-05-252013-08-14Us
Tru-micinLipoic Acid (0.01 g/100mL) + Ginger (0.01 g/100mL) + Indian frankincense (0.01 g/100mL) + Ocimum tenuiflorum top (0.01 g/100mL) + Rosemary (0.01 g/100mL) + Salix alba bark (0.01 g/100mL) + Turmeric (0.01 g/100mL)LotionTopicalTruceuticals, Llc2011-05-252013-08-14Us
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DyzbacLipoic Acid (125 mg/1) + Ascorbic acid (150 mg/1) + Cholecalciferol (0.0125 mg/1) + Leucovorin (1 mg/1) + Methylcobalamin (1 mg/1) + Pyridoxal Phosphate (12.5 mg/1) + Resveratrol (50 mg/1) + Ubidecarenone (50 mg/1)TabletOralBasiem2015-10-282015-11-01Us
DyzbacLipoic Acid (150 mg/1) + Ascorbic acid (125 mg/1) + Cholecalciferol (500 [iU]/1) + Leucovorin (1 mg/1) + Methylcobalamin (1 mg/1) + Pyridoxal Phosphate (12.5 mg/1) + Resveratrol (50 mg/1) + Ubidecarenone (25 mg/1)TabletOralBasiem2015-11-052016-01-01Us
MebolexLipoic Acid (150 mg/1) + Ascorbic acid (125 mg/1) + Cholecalciferol (0.0125 mg/1) + Leucovorin (1 mg/1) + Methylcobalamin (1 mg/1) + Pyridoxal Phosphate (12.5 mg/1) + Resveratrol (50 mg/1) + Ubidecarenone (25 mg/1)TabletOralSolubiomix2015-10-282016-01-01Us
Medi-10Lipoic Acid (200 mg/1) + Acetylcysteine (200 mg/1) + Cholecalciferol (1000 [iU]/1) + Chromium picolinate (1 mg/1) + Levomefolate calcium (2.5 mg/1) + Methylcobalamin (2.5 mg/1) + Nicotinamide (10 mg/1) + Pyridoxal Phosphate (20 mg/1) + Resveratrol (83 mg/1) + Ubidecarenone (16 mg/1)CapsuleOralMedicap Laboratories Inc.2015-05-012016-01-12Us
MethazelLipoic Acid (50 mg/1) + Acetylcysteine (50 mg/1) + Folic Acid (1 mg/1) + Methylcobalamin (2.5 mg/1) + Pyridoxal Phosphate (50 mg/1) + Coenzyme q10, (2z)- (25 mg/1)CapsuleOralSterling-Knight Pharmaceuticals, LLC2015-10-12Not applicableUs
Strovite One CapletsLipoic Acid (15 mg/1) + Ascorbic acid (300 mg/1) + Biotin (100 ug/1) + Cholecalciferol (1000 [iU]/1) + Chromium (50 ug/1) + Cupric sulfate pentahydrate (1.5 mg/1) + Cyanocobalamin (50 ug/1) + Folic Acid (1 mg/1) + Lutein (5 mg/1) + Magnesium oxide (50 mg/1) + Manganese (1.5 mg/1) + Nicotinamide (25 mg/1) + Calcium pantothenate (7.5 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (5 mg/1) + Selenium (100 ug/1) + Thiamine chloride (20 mg/1) + Vitamin A (3000 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol succinate (100 [iU]/1)TabletOralExeltis Usa, Inc.2001-05-04Not applicableUs
Vita-Rx Diabetic VitaminLipoic Acid (150 mg/1) + Ascorbic acid (120 mg/1) + Biotin (2.5 mg/1) + Cholecalciferol (0.0625 mg/1) + Chromium picolinate (0.465 mg/1) + Folic Acid (0.8 mg/1) + Methylcobalamin (0.0025 mg/1) + Niacin (20 mg/1) + Calcium pantothenate (10 mg/1) + Pyridoxal Phosphate (12.5 mg/1) + Riboflavin (1.7 mg/1) + Thiamine mononitrate (1.5 mg/1) + Ubidecarenone (50 mg/1) + alpha-Tocopherol acetate (10 mg/1)Capsule, gelatin coatedOralPure Source, Llc2015-08-11Not applicableUs
Vita-Rx Diabetic VitaminLipoic Acid (150 mg/1) + Ascorbic acid (120 mg/1) + Biotin (2.5 mg/1) + Cholecalciferol (0.0625 mg/1) + Chromium picolinate (0.465 mg/1) + Folic Acid (0.8 mg/1) + Methylcobalamin (0.0025 mg/1) + Niacin (20 mg/1) + Calcium pantothenate (10 mg/1) + Pyridoxal Phosphate (12.5 mg/1) + Riboflavin (1.7 mg/1) + Thiamine mononitrate (1.5 mg/1) + Ubidecarenone (50 mg/1) + alpha-Tocopherol acetate (10 mg/1)Capsule, gelatin coatedOralMas Management Group Inc.2015-08-11Not applicableUs
International/Other Brands
Biletan
Categories
UNII
VLL71EBS9Z
CAS number
1200-22-2
Weight
Average: 206.326
Monoisotopic: 206.043521072
Chemical Formula
C8H14O2S2
InChI Key
AGBQKNBQESQNJD-SSDOTTSWSA-N
InChI
InChI=1S/C8H14O2S2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H,9,10)/t7-/m1/s1
IUPAC Name
5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid
SMILES
OC(=O)CCCC[C@@H]1CCSS1

Pharmacology

Indication

For nutritional supplementation, also for treating dietary shortage or imbalance.

Pharmacodynamics

Lipoic acid (or α-lipoic acid) is able to pass the blood-brain barrier and is putatively used for detoxification of mercury attached to the brain cells. It can mobilise bound mercury into the blood stream as it is a mercaptan (sulfur compound which readily binds to the mercury). In the blood stream, another chelator such as dimercaptosuccinic acid (DMSA) or methylsulfonylmethane (MSM) is used to transfer mercury safely into the urine for excretion. Neither DMSA nor MSM can cross the blood-brain barrier, which is why both lipoic acid and DMSA are used. It is hypothesized that this treatment-along with carnitine, dimethylglycine (DMG), Vitamin B6, folic acid, and magnesium—could be used to treat autism and amalgam poisoning. In this hypothesis, the reason why autism is difficult to treat is that mercury is attached to the brain cells and most medicines and vitamin supplements do not penetrate the blood-brain barrier. However, α-lipoic acid and perhaps vitamin B12 could making it possible for other chelators to remove mercury safely out of the body and could perhaps one day be used as a treatment for autism. Because lipoic acid is related to cellular uptake of glucose and it is both soluble in water and fat, it is being used for treatment in diabetes. It may be helpful for people with Alzheimer's disease or Parkinson's disease.

Mechanism of action

Lipoic Acid is generally involved in oxidative decarboxylations of keto acids and is presented as a growth factor for some organisms. Lipoic acid exists as two enantiomers, the R-enantiomer and the S-enantiomer. Normally only the R-enantiomer of an amino acid is biologically active, but for lipoic acid the S-enantiomer assists in the reduction of the R-enantiomer when a racemic mixture is given. Some recent studies have suggested that the S-enantiomer in fact has an inhibiting effect on the R-enantiomer, reducing its biological activity substantially and actually adding to oxidative stress rather than reducing it. Furthermore, the S-enantiomer has been found to reduce the expression of GLUT-4s in cells, responsible for glucose uptake, and hence reduce insulin sensitivity.

TargetActionsOrganism
ULipoyltransferase 1, mitochondrialNot AvailableHuman
ULipoyl synthase, mitochondrialNot AvailableHuman
USodium-dependent multivitamin transporterNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,4-thiazolidinedioneThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with 2,4-thiazolidinedione.
AcarboseThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with Acarbose.
AcetohexamideThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with Acetohexamide.
AICA ribonucleotideThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with AICA ribonucleotide.
AlaproclateThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with Alaproclate.
AlbiglutideThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with Albiglutide.
AlogliptinThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with Alogliptin.
AMG-222The risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with AMG-222.
AnagliptinThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with Anagliptin.
BalaglitazoneThe risk or severity of hypoglycemia can be increased when Lipoic Acid is combined with Balaglitazone.
Food Interactions
Not Available

References

Synthesis Reference

Joachim Paust, Peter Eckes, Wolfgang Siegel, Friedhelm Balkenhohl, Walter Dobler, Michael Hullmann, "Preparation of R/S-.gamma.-lipoic acid or R/S-.alpha.-lipoic acid." U.S. Patent US5489694, issued July, 1961.

US5489694
General References
  1. Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [PubMed:10966480]
  2. REED LJ, DeBUSK BG, GUNSALUS IC, HORNBERGER CS Jr: Crystalline alpha-lipoic acid; a catalytic agent associated with pyruvate dehydrogenase. Science. 1951 Jul 27;114(2952):93-4. [PubMed:14854913]
External Links
Human Metabolome Database
HMDB0014312
KEGG Drug
D00086
KEGG Compound
C16241
PubChem Compound
6112
PubChem Substance
46504826
ChemSpider
5886
BindingDB
50106731
ChEBI
30314
ChEMBL
CHEMBL134342
PharmGKB
PA164776929
HET
LPA
Wikipedia
Lipoic_acid
ATC Codes
A16AX01 — Thioctic acid
PDB Entries
1hpc / 1x2h / 2art / 2c8m / 2iqd / 5iby / 5ij6 / 5t8u
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAlzheimer's Disease (AD)1
1CompletedTreatmentDisseminated Sclerosis1
1RecruitingTreatmentDisseminated Sclerosis / Multiple Sclerosis, Primary Progressive / Progressive Multiple Sclerosis / Secondary Progressive Multiple Sclerosis (SPMS)1
1Unknown StatusTreatmentOptic Neuritis1
1Unknown StatusTreatmentProgressive Supranuclear Palsy (PSP)1
1, 2Active Not RecruitingTreatmentAge-Related Macular Degeneration (ARMD)1
1, 2CompletedTreatmentDisseminated Sclerosis1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) / Peripheral Neuropathy1
1, 2CompletedTreatmentPeripheral Neuropathy1
1, 2Unknown StatusTreatmentAlzheimer's Disease (AD)1
2CompletedPreventionCesarean Scar Niche / Cesarean Section; Dehiscence1
2CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAdrenomyeloneuropathy1
2CompletedTreatmentCarpal Tunnel Syndrome (CTS)1
2CompletedTreatmentChronic Inflammatory Demyelinating Polyneuropathy (CIDP) / Polyradiculoneuropathy, Chronic Inflammatory Demyelinating1
2CompletedTreatmentChronic Kidney Disease (CKD)1
2CompletedTreatmentCognitive Disorders / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentEnd-Stage Renal Disease (ESRD)1
2CompletedTreatmentHigh Cholesterol1
2CompletedTreatmentType 2 Diabetes Mellitus1
2Not Yet RecruitingTreatmentTherapeutic Agent Toxicity1
2RecruitingTreatmentDisseminated Sclerosis1
2Unknown StatusTreatmentType 2 Diabetes Mellitus1
2, 3CompletedSupportive CareOtotoxicity / Unspecified Adult Solid Tumor1
2, 3CompletedTreatmentMultiple Sclerosis, Chronic Progressive1
2, 3Unknown StatusTreatmentDiabetics1
3CompletedSupportive CareNeurologic toxicity / Unspecified Adult Solid Tumor, Protocol Specific / Unspecified Childhood Solid Tumor, Protocol Specific1
3CompletedTreatmentDiabetic Polyneuropathy2
4CompletedBasic SciencePre-Diabetic / Type 2 Diabetes Mellitus1
4CompletedPreventionCoronary Artery Disease / Left Ventricular Mass / Type 2 Diabetes Mellitus1
4CompletedTreatmentCardiac Autonomic Neuropathy / Type 2 Diabetes Mellitus1
4CompletedTreatmentDiabetic Neuropathies1
4CompletedTreatmentNervous System Diseases, Sympathetic / Takotsubo Cardiomyopathy1
4Not Yet RecruitingOtherIschemic Heart Failure1
4TerminatedPreventionNASH (Non-alcoholic Steato-hepatitis)1
4Unknown StatusPreventionAcute Kidney Injury (AKI) / The Changes of Endothelium-dependent Arterial Dilation / The Changes of Plasma Creatinine / The Changes of Plasma Free Radicals1
Not AvailableCompletedPreventionImpaired Glucose Tolerance (IGT) / Prediabetic State1
Not AvailableCompletedTreatmentAntioxidants / Blastocyst / Culture Media / Embryo / Humans1
Not AvailableCompletedTreatmentDiabetes Mellitus (DM) / High Blood Pressure (Hypertension)1
Not AvailableCompletedTreatmentMitochondrial Myopathies1
Not AvailableNot Yet RecruitingTreatmentPolycystic Ovaries Syndrome1
Not AvailableRecruitingTreatmentAntioxidants / Blastocyst / Culture Media / Embryo / Humans / Oxygen1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Freeda Vitamins
  • Mason Distributors
  • Spectrum Pharmaceuticals
  • Sundown Inc.
  • Tyler Encapsulations
Dosage forms
FormRouteStrength
TabletOral
CapsuleOral
CreamTopical
LotionTopical
Capsule, gelatin coatedOral
Prices
Unit descriptionCostUnit
Lipoic acid powder77.35USD g
Lipoic acid capsule0.26USD capsule
Alpha lipoic acid 200 mg tablet0.22USD tablet
Alpha-lipoic acid 50 mg caplet0.16USD caplet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)60.5 °CPhysProp
boiling point (°C)162.5 °CPhysProp
water solubilityInsolubleNot Available
logP2.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.224 mg/mLALOGPS
logP2.75ALOGPS
logP2.11ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.52ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity54.37 m3·mol-1ChemAxon
Polarizability21.74 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9695
Blood Brain Barrier+0.9749
Caco-2 permeable-0.5385
P-glycoprotein substrateNon-substrate0.7248
P-glycoprotein inhibitor INon-inhibitor0.9526
P-glycoprotein inhibitor IINon-inhibitor0.9856
Renal organic cation transporterNon-inhibitor0.8373
CYP450 2C9 substrateNon-substrate0.7961
CYP450 2D6 substrateNon-substrate0.8334
CYP450 3A4 substrateNon-substrate0.7346
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9365
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9301
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.8721
BiodegradationReady biodegradable0.7788
Rat acute toxicity2.2921 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9452
hERG inhibition (predictor II)Non-inhibitor0.9451
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.4 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0aba-3900000000-46fc1d57abcc26f6720e
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0a4r-0940000000-dead1b29e79e0002da2a
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0f8c-9200000000-b6035bdb4abd0d267297
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0059-9000000000-62e73cabbac1531f5145
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as lipoic acids and derivatives. These are compounds containing a lipoic acid moiety (or a derivative thereof), which consists of a pentanoic acid (or derivative) attached to the C3 carbon atom of a 1,2-dithiolane ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Dithiolanes
Sub Class
Lipoic acids and derivatives
Direct Parent
Lipoic acids and derivatives
Alternative Parents
Medium-chain fatty acids / Thia fatty acids / Heterocyclic fatty acids / 1,2-dithiolanes / Organic disulfides / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Lipoic_acid_derivative / Medium-chain fatty acid / Heterocyclic fatty acid / Thia fatty acid / Fatty acyl / Fatty acid / 1,2-dithiolane / Organic disulfide / Monocarboxylic acid or derivatives / Carboxylic acid
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
dithiolanes, thia fatty acid, heterocyclic fatty acid, lipoic acid (CHEBI:30314) / Thia fatty acids (C16241) / Thia fatty acids (LMFA01130001)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity, transferring acyl groups
Specific Function
Catalyzes the transfer of the lipoyl group from lipoyl-AMP to the specific lysine residue of lipoyl domains of lipoate-dependent enzymes.
Gene Name
LIPT1
Uniprot ID
Q9Y234
Uniprot Name
Lipoyltransferase 1, mitochondrial
Molecular Weight
42478.8 Da
References
  1. Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. [PubMed:16246025]
  2. Fujiwara K, Toma S, Okamura-Ikeda K, Motokawa Y, Nakagawa A, Taniguchi H: Crystal structure of lipoate-protein ligase A from Escherichia coli. Determination of the lipoic acid-binding site. J Biol Chem. 2005 Sep 30;280(39):33645-51. Epub 2005 Jul 25. [PubMed:16043486]
  3. Gueguen V, Macherel D, Neuburger M, Pierre CS, Jaquinod M, Gans P, Douce R, Bourguignon J: Structural and functional characterization of H protein mutants of the glycine decarboxylase complex. J Biol Chem. 1999 Sep 10;274(37):26344-52. [PubMed:10473591]
  4. Macherel D, Bourguignon J, Forest E, Faure M, Cohen-Addad C, Douce R: Expression, lipoylation and structure determination of recombinant pea H-protein in Escherichia coli. Eur J Biochem. 1996 Feb 15;236(1):27-33. [PubMed:8617275]
  5. Fujiwara K, Hosaka H, Matsuda M, Okamura-Ikeda K, Motokawa Y, Suzuki M, Nakagawa A, Taniguchi H: Crystal structure of bovine lipoyltransferase in complex with lipoyl-AMP. J Mol Biol. 2007 Aug 3;371(1):222-34. Epub 2007 May 26. [PubMed:17570395]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Catalyzes the radical-mediated insertion of two sulfur atoms into the C-6 and C-8 positions of the octanoyl moiety bound to the lipoyl domains of lipoate-dependent enzymes, thereby converting the o...
Gene Name
LIAS
Uniprot ID
O43766
Uniprot Name
Lipoyl synthase, mitochondrial
Molecular Weight
41910.695 Da
References
  1. Morikawa T, Yasuno R, Wada H: Do mammalian cells synthesize lipoic acid? Identification of a mouse cDNA encoding a lipoic acid synthase located in mitochondria. FEBS Lett. 2001 Jun 1;498(1):16-21. [PubMed:11389890]
  2. Yasuno R, Wada H: Biosynthesis of lipoic acid in Arabidopsis: cloning and characterization of the cDNA for lipoic acid synthase. Plant Physiol. 1998 Nov;118(3):935-43. [PubMed:9808738]
  3. Ollagnier-de Choudens S, Fontecave M: The lipoate synthase from Escherichia coli is an iron-sulfur protein. FEBS Lett. 1999 Jun 18;453(1-2):25-8. [PubMed:10403368]
  4. Wrenger C, Muller S: The human malaria parasite Plasmodium falciparum has distinct organelle-specific lipoylation pathways. Mol Microbiol. 2004 Jul;53(1):103-13. [PubMed:15225307]
  5. Gunther S, McMillan PJ, Wallace LJ, Muller S: Plasmodium falciparum possesses organelle-specific alpha-keto acid dehydrogenase complexes and lipoylation pathways. Biochem Soc Trans. 2005 Nov;33(Pt 5):977-80. [PubMed:16246025]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sodium-dependent multivitamin transmembrane transporter activity
Specific Function
Transports pantothenate, biotin and lipoate in the presence of sodium.
Gene Name
SLC5A6
Uniprot ID
Q9Y289
Uniprot Name
Sodium-dependent multivitamin transporter
Molecular Weight
68641.27 Da
References
  1. Prasad PD, Wang H, Huang W, Fei YJ, Leibach FH, Devoe LD, Ganapathy V: Molecular and functional characterization of the intestinal Na+-dependent multivitamin transporter. Arch Biochem Biophys. 1999 Jun 1;366(1):95-106. [PubMed:10334869]
  2. Dey S, Subramanian VS, Chatterjee NS, Rubin SA, Said HM: Characterization of the 5' regulatory region of the human sodium-dependent multivitamin transporter, hSMVT. Biochim Biophys Acta. 2002 Mar 19;1574(2):187-92. [PubMed:11955628]
  3. Griffin JB, Stanley JS, Zempleni J: Synthesis of a rabbit polyclonal antibody to the human sodium-dependent multivitamin transporter. Int J Vitam Nutr Res. 2002 Jul;72(4):195-8. [PubMed:12214555]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name
POR
Uniprot ID
P16435
Uniprot Name
NADPH--cytochrome P450 reductase
Molecular Weight
76689.12 Da
References
  1. Dudka J: Decrease in NADPH-cytochrome P450 reductase activity of the human heart, Liver and lungs in the presence of alpha-lipoic acid. Ann Nutr Metab. 2006;50(2):121-5. Epub 2006 Jan 2. [PubMed:16391466]
  2. Wen B, Coe KJ, Rademacher P, Fitch WL, Monshouwer M, Nelson SD: Comparison of in vitro bioactivation of flutamide and its cyano analogue: evidence for reductive activation by human NADPH:cytochrome P450 reductase. Chem Res Toxicol. 2008 Dec;21(12):2393-406. doi: 10.1021/tx800281h. [PubMed:19548358]
  3. Gan L, von Moltke LL, Trepanier LA, Harmatz JS, Greenblatt DJ, Court MH: Role of NADPH-cytochrome P450 reductase and cytochrome-b5/NADH-b5 reductase in variability of CYP3A activity in human liver microsomes. Drug Metab Dispos. 2009 Jan;37(1):90-6. doi: 10.1124/dmd.108.023424. Epub 2008 Oct 6. [PubMed:18838505]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 04:38