Identification
NameLipoic Acid
Accession NumberDB00166  (NUTR00035)
TypeSmall Molecule
GroupsApproved, 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-Liponsäure
D-thioctic acid
R-(+)-thioctic acid
R-alpha-lipoic acid
Thioctic acid D-form
α-lipoic acid
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BiletanNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Strovite One CapletsTabletOralEverett Laboratories, Inc.2001-05-04Not applicableUs
Categories
UNIIVLL71EBS9Z
CAS number1200-22-2
WeightAverage: 206.326
Monoisotopic: 206.043521072
Chemical FormulaC8H14O2S2
InChI KeyAGBQKNBQESQNJD-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.

Structured Indications Not Available
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Lipoyltransferase 1, mitochondrialProteinunknownNot AvailableHumanQ9Y234 details
Sodium-dependent multivitamin transporterProteinunknownNot AvailableHumanQ9Y289 details
Lipoyl synthase, mitochondrialProteinunknownNot AvailableHumanO43766 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,4-thiazolidinedioneLipoic Acid may increase the hypoglycemic activities of Thiazolidinedione.Investigational
AcarboseLipoic Acid may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AcetohexamideLipoic Acid may increase the hypoglycemic activities of Acetohexamide.Withdrawn
AICA ribonucleotideLipoic Acid may increase the hypoglycemic activities of Aicar.Experimental
AlogliptinLipoic Acid may increase the hypoglycemic activities of Alogliptin.Approved
BalaglitazoneLipoic Acid may increase the hypoglycemic activities of Balaglitazone.Investigational
BuforminLipoic Acid may increase the hypoglycemic activities of Buformin.Withdrawn
CalciumCalcium can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Nutraceutical
Calcium AcetateCalcium Acetate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium CarbonateCalcium carbonate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium ChlorideCalcium Chloride can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium CitrateCalcium citrate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium glubionateCalcium glubionate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium GluceptateCalcium Gluceptate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Calcium gluconateCalcium gluconate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
CanagliflozinLipoic Acid may increase the hypoglycemic activities of Canagliflozin.Approved
CastanospermineLipoic Acid may increase the hypoglycemic activities of Castanospermine.Experimental
ChlorpropamideLipoic Acid may increase the hypoglycemic activities of Chlorpropamide.Approved
CiglitazoneLipoic Acid may increase the hypoglycemic activities of Ciglitazone.Experimental
CisplatinThe therapeutic efficacy of Cisplatin can be decreased when used in combination with Lipoic Acid.Approved
DeoxyspergualinLipoic Acid may increase the hypoglycemic activities of Deoxyspergualin.Investigational
DulaglutideLipoic Acid may increase the hypoglycemic activities of Dulaglutide.Approved
EmpagliflozinLipoic Acid may increase the hypoglycemic activities of Empagliflozin.Approved
ExenatideLipoic Acid may increase the hypoglycemic activities of Exenatide.Approved, Investigational
Ferric CarboxymaltoseFerric Carboxymaltose can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Ferric CitrateFerric Citrate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Ferric pyrophosphateFerric pyrophosphate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
GlibornurideLipoic Acid may increase the hypoglycemic activities of Glibornuride.Withdrawn
GliclazideLipoic Acid may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideLipoic Acid may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideLipoic Acid may increase the hypoglycemic activities of Glipizide.Approved
GliquidoneLipoic Acid may increase the hypoglycemic activities of Gliquidone.Approved
GlyburideLipoic Acid may increase the hypoglycemic activities of Glyburide.Approved
GusperimusLipoic Acid may increase the hypoglycemic activities of Gusperimus.Investigational
Insulin AspartLipoic Acid may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirLipoic Acid may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineLipoic Acid may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineLipoic Acid may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin LisproLipoic Acid may increase the hypoglycemic activities of Insulin Lispro.Approved
Insulin PorkLipoic Acid may increase the hypoglycemic activities of Insulin Pork.Approved
IronIron can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Iron DextranIron Dextran can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
Iron saccharateIron saccharate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
LinagliptinLipoic Acid may increase the hypoglycemic activities of Linagliptin.Approved
LiraglutideLipoic Acid may increase the hypoglycemic activities of Liraglutide.Approved
Magnesium HydroxideMagnesium hydroxide can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium salicylateMagnesium salicylate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium SulfateMagnesium Sulfate can cause a decrease in the absorption of Lipoic Acid resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved, Vet Approved
MetforminLipoic Acid may increase the hypoglycemic activities of Metformin.Approved
MiglitolLipoic Acid may increase the hypoglycemic activities of Miglitol.Approved
MiglustatLipoic Acid may increase the hypoglycemic activities of Miglustat.Approved
MitiglinideLipoic Acid may increase the hypoglycemic activities of Mitiglinide.Approved, Investigational
NateglinideLipoic Acid may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
PhenforminLipoic Acid may increase the hypoglycemic activities of Phenformin.Approved, Withdrawn
PioglitazoneLipoic Acid may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PramlintideLipoic Acid may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
RepaglinideLipoic Acid may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RosiglitazoneLipoic Acid may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SaxagliptinLipoic Acid may increase the hypoglycemic activities of Saxagliptin.Approved
SitagliptinLipoic Acid may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SulodexideLipoic Acid may increase the hypoglycemic activities of Sulodexide.Approved, Investigational
TolazamideLipoic Acid may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideLipoic Acid may increase the hypoglycemic activities of Tolbutamide.Approved
TroglitazoneLipoic Acid may increase the hypoglycemic activities of Troglitazone.Withdrawn
VildagliptinLipoic Acid may increase the hypoglycemic activities of Vildagliptin.Approved, Investigational
VogliboseLipoic Acid may increase the hypoglycemic activities of Voglibose.Approved, Investigational
Food InteractionsNot 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
ATC CodesA16AX01 — Thioctic acid
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.1 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAlzheimer's Disease (AD)1
1CompletedTreatmentDisseminated Sclerosis1
1Unknown StatusTreatmentOptic Neuritis1
1Unknown StatusTreatmentProgressive Supranuclear Palsy (PSP)1
1, 2CompletedTreatmentDisseminated Sclerosis1
1, 2CompletedTreatmentHIV Disease / Peripheral Neuropathy1
1, 2CompletedTreatmentPeripheral Neuropathy1
1, 2RecruitingTreatmentAge-Related Macular Degeneration (ARMD)1
1, 2Unknown StatusTreatmentAlzheimer's Disease (AD)1
2CompletedTreatmentAdrenomyeloneuropathy1
2CompletedTreatmentChronic Inflammatory Demyelinating Polyneuropathy (CIDP) / Polyradiculoneuropathy, Chronic Inflammatory Demyelinating1
2CompletedTreatmentCognitive Disorders / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHypercholesterolaemia1
2Not Yet RecruitingTreatmentDisseminated Sclerosis1
2Not Yet RecruitingTreatmentToxicity1
2Unknown StatusTreatmentType 2 Diabetes Mellitus1
2, 3CompletedSupportive CareOtotoxicity / Unspecified Adult Solid Tumor1
2, 3CompletedTreatmentMultiple Sclerosis, Chronic Progressive1
2, 3Unknown StatusTreatmentDiabetics1
3CompletedSupportive CareNeurotoxicity / 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
4TerminatedPreventionNASH (Non-alcoholic Steato-hepatitis)1
Not AvailableCompletedTreatmentDiabetes / Hypertensive1
Not AvailableCompletedTreatmentMitochondrial Myopathies1
Not AvailableNot Yet RecruitingTreatmentPolycystic Ovaries Syndrome1
Not AvailableRecruitingTreatmentAntioxidants / Blastocyst / Culture Media / Embryo / Humans1
Not AvailableRecruitingTreatmentAntioxidants / Blastocyst / Culture Media / Embryo / Humans / Oxygen1
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
TabletOral
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.
PatentsNot Available
Properties
StateSolid
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0aba-3900000000-46fc1d57abcc26f6720eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4r-0940000000-dead1b29e79e0002da2aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0f8c-9200000000-b6035bdb4abd0d267297View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0059-9000000000-62e73cabbac1531f5145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
ClassificationNot classified

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:
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 ]
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 octanoylated domains into lipoylated derivatives.
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 ]

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 August 02, 2017 16:20