Lipoic acid

Identification

Generic Name
Lipoic acid
DrugBank Accession Number
DB00166
Background

A vitamin-like antioxidant.

Type
Small Molecule
Groups
Approved, Investigational, Nutraceutical
Structure
Weight
Average: 206.326
Monoisotopic: 206.043521072
Chemical Formula
C8H14O2S2
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
  • Lipoic acid
  • R-(+)-thioctic acid
  • R-alpha-lipoic acid
  • Thioctic acid
  • Thioctic acid D-form
  • α-lipoic acid

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination for symptomatic treatment ofDiabetic neuropathiesCombination Product in combination with: Nateglinide (DB00731)•••••••••••••••••
Used in combination to manageType 2 diabetes mellitusCombination Product in combination with: Nateglinide (DB00731)•••••••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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. Since DMSA cannot cross the blood-brain barrier, both lipoic acid and DMSA tend to be used together.3,4 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 AvailableHumans
USodium-dependent multivitamin transporterNot AvailableHumans
ULipoyl synthase, mitochondrialNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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.
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.
BexagliflozinThe risk or severity of hypoglycemia can be increased when Lipoic acid is combined with Bexagliflozin.
Food Interactions
No interactions found.

Products

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International/Other Brands
Biletan
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
APIKOBAL PLUS 250/250/1/300 MG ENTERIK KAPLI TABLET, 30 ADETLipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg)Tablet, delayed releaseOralSANTA FARMA İLAÇ SAN. A.Ş.2016-11-29Not applicableTurkey flag
APIKOBAL PLUS 250/250/1/300 MG ENTERIK KAPLI TABLET, 50 ADETLipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg)Tablet, delayed releaseOralSANTA FARMA İLAÇ SAN. A.Ş.2016-11-29Not applicableTurkey flag
BENEDAY 250/250/1/300 MG 50 ENTERIK KAPLI TABLETLipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg)Tablet, delayed releaseOralTAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ.2015-01-292023-04-25Turkey flag
CHALİA 250/250/1/300 MG GASTRO-REZİSTAN TABLET, 30 ADETLipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg)Tablet, delayed releaseOralSANOVEL İLAÇ SAN. VE TİC. A.Ş.2020-06-26Not applicableTurkey flag
CHALİA 250/250/1/300 MG GASTRO-REZİSTAN TABLET, 50 ADETLipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg)Tablet, delayed releaseOralSANOVEL İLAÇ SAN. VE TİC. A.Ş.2020-06-26Not applicableTurkey flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DyzbacLipoic acid (150 mg/1) + Ascorbic acid (125 mg/1) + Cholecalciferol (500 [iU]/1) + Leucovorin (1 mg/1) + Mecobalamin (1 mg/1) + Pyridoxal phosphate (12.5 mg/1) + Resveratrol (50 mg/1) + Ubidecarenone (25 mg/1)TabletOralBasiem2015-11-052016-01-01US flag
DyzbacLipoic acid (125 mg/1) + Ascorbic acid (150 mg/1) + Cholecalciferol (0.0125 mg/1) + Leucovorin (1 mg/1) + Mecobalamin (1 mg/1) + Pyridoxal phosphate (12.5 mg/1) + Resveratrol (50 mg/1) + Ubidecarenone (50 mg/1)TabletOralBasiem2015-10-282015-11-01US flag
MebolexLipoic acid (150 mg/1) + Ascorbic acid (125 mg/1) + Cholecalciferol (0.0125 mg/1) + Leucovorin (1 mg/1) + Mecobalamin (1 mg/1) + Pyridoxal phosphate (12.5 mg/1) + Resveratrol (50 mg/1) + Ubidecarenone (25 mg/1)TabletOralSolubiomix2015-10-282016-01-01US flag
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) + Mecobalamin (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 flag
MethazelLipoic acid (50 mg/1) + Acetylcysteine (50 mg/1) + Folic acid (1 mg/1) + Mecobalamin (2.5 mg/1) + Pyridoxal phosphate (50 mg/1) + Coenzyme q10, (2z)- (25 mg/1)CapsuleOralSterling-Knight Pharmaceuticals, LLC2015-10-122019-12-01US flag

Categories

ATC Codes
A16AX01 — Thioctic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-dithiolane / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acid / Fatty acyl / Heterocyclic fatty acid / Hydrocarbon derivative / Lipoic_acid_derivative
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)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
VLL71EBS9Z
CAS number
1200-22-2
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

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. [Article]
  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. [Article]
  3. Arnold J, Morgan B: Management of Lead Encephalopathy with DMSA After Exposure to Lead-Contaminated Moonshine. J Med Toxicol. 2015 Dec;11(4):464-7. doi: 10.1007/s13181-015-0493-9. [Article]
  4. Patwa J, Thakur A, Flora SJS: Alpha Lipoic Acid and Monoisoamyl-DMSA Combined Treatment Ameliorates Copper-Induced Neurobehavioral Deficits, Oxidative Stress, and Inflammation. Toxics. 2022 Nov 24;10(12):718. doi: 10.3390/toxics10120718. [Article]
  5. MS Society Canada: Lipoic Acid [Link]
Human Metabolome Database
HMDB0001451
KEGG Drug
D00086
KEGG Compound
C16241
PubChem Compound
6112
PubChem Substance
46504826
ChemSpider
5886
BindingDB
50106731
RxNav
6417
ChEBI
30314
ChEMBL
CHEMBL134342
ZINC
ZINC000001544807
PharmGKB
PA164776929
PDBe Ligand
LPA
Wikipedia
Lipoic_acid
PDB Entries
1hpc / 1x2h / 2art / 2c8m / 2iqd / 5iby / 5ij6 / 5t8u / 7yva / 8cri
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Freeda Vitamins
  • Mason Distributors
  • Spectrum Pharmaceuticals
  • Sundown Inc.
  • Tyler Encapsulations
Dosage Forms
FormRouteStrength
SolutionIntravenous60000000 mg
Tablet, extended releaseOral
CapsuleOral
SolutionParenteral600 MG
Injection, solutionParenteral600 MG
CapsuleOral300 MG
CapsuleOral600 MG
Tablet, delayed releaseOral
Tablet, film coatedOral600 mg/1
Tablet, coatedOral
TabletOral
CapsuleOral100 mg
Injection, solution600 mg/50ml
Injection, solution
CapsuleOral50 mg
Tablet, film coatedOral60000000 mg
Tablet, coatedOral300 mg
CapsuleOral
Tablet, film coatedOral
CreamTopical
TabletOral600 mg
Capsule, liquid filledOral
Tablet, film coatedOral200 mg
TabletOral600.000 mg
Injection, solutionIntravenous600 mg/24ml
Injection, solutionIntravenous600 mg/50ml
SolutionIntravenous600.000 mg
Injection, solutionIntravenous
Injection, solutionIntravenous600 mg
Tablet, film coatedOral600 mg
Tablet, coatedOral600 mg
SolutionIntravenous600 mg
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-MSsplash10-0ufu-5900000000-716655e029db4b97efd9
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/MSsplash10-0a4r-0980000000-7113d91586bc9d7a2ac7
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0490000000-da27f0ca21198ab19cb3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pb9-9820000000-5a9c64b5bd1e2b198d01
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03ka-3900000000-ed32851760f4d9043096
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-4900000000-fbc33bf225671a461fe8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-3900000000-a1ec533249a498b72fa1
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-147.9945289
predicted
DarkChem Lite v0.1.0
[M-H]-147.0469289
predicted
DarkChem Lite v0.1.0
[M-H]-147.0686289
predicted
DarkChem Lite v0.1.0
[M-H]-148.0634289
predicted
DarkChem Lite v0.1.0
[M-H]-139.93855
predicted
DeepCCS 1.0 (2019)
[M+H]+142.33412
predicted
DeepCCS 1.0 (2019)
[M+Na]+149.63976
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 06, 2024 03:02