Identification
- Generic Name
- Lipoic acid
- DrugBank Accession Number
- DB00166
- Background
A vitamin-like antioxidant.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
Structure for Lipoic acid (DB00166)
- 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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Diabetic neuropathies Combination Product in combination with: Nateglinide (DB00731) •••••••••••• ••••• Used in combination to manage Type 2 diabetes mellitus Combination Product in combination with: Nateglinide (DB00731) •••••••••••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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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.
Target Actions Organism ULipoyltransferase 1, mitochondrial Not Available Humans USodium-dependent multivitamin transporter Not Available Humans ULipoyl synthase, mitochondrial Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The risk or severity of hypoglycemia can be increased when Lipoic acid is combined with Acarbose. Acetohexamide The risk or severity of hypoglycemia can be increased when Lipoic acid is combined with Acetohexamide. Albiglutide The risk or severity of hypoglycemia can be increased when Lipoic acid is combined with Albiglutide. Alogliptin The risk or severity of hypoglycemia can be increased when Lipoic acid is combined with Alogliptin. Bexagliflozin The risk or severity of hypoglycemia can be increased when Lipoic acid is combined with Bexagliflozin. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Biletan
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image APIKOBAL PLUS 250/250/1/300 MG ENTERIK KAPLI TABLET, 30 ADET Lipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg) Tablet, delayed release Oral SANTA FARMA İLAÇ SAN. A.Ş. 2016-11-29 Not applicable Turkey 
APIKOBAL PLUS 250/250/1/300 MG ENTERIK KAPLI TABLET, 50 ADET Lipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg) Tablet, delayed release Oral SANTA FARMA İLAÇ SAN. A.Ş. 2016-11-29 Not applicable Turkey BENEDAY 250/250/1/300 MG 50 ENTERIK KAPLI TABLET Lipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg) Tablet, delayed release Oral TAKEDA İLAÇ SAĞLIK SAN. TİC. LTD. ŞTİ. 2015-01-29 2023-04-25 Turkey CHALİA 250/250/1/300 MG GASTRO-REZİSTAN TABLET, 30 ADET Lipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg) Tablet, delayed release Oral SANOVEL İLAÇ SAN. VE TİC. A.Ş. 2020-06-26 Not applicable Turkey CHALİA 250/250/1/300 MG GASTRO-REZİSTAN TABLET, 50 ADET Lipoic acid (300 mg) + Cyanocobalamin (1 mg) + Pyridoxine (250 mg) + Thiamine (250 mg) Tablet, delayed release Oral SANOVEL İLAÇ SAN. VE TİC. A.Ş. 2020-06-26 Not applicable Turkey - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Dyzbac Lipoic 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) Tablet Oral Basiem 2015-11-05 2016-01-01 US 
Dyzbac Lipoic 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) Tablet Oral Basiem 2015-10-28 2015-11-01 US Mebolex Lipoic 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) Tablet Oral Solubiomix 2015-10-28 2016-01-01 US Medi-10 Lipoic 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) Capsule Oral Medicap Laboratories Inc. 2015-05-01 2016-01-12 US Methazel Lipoic 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) Capsule Oral Sterling-Knight Pharmaceuticals, LLC 2015-10-12 2019-12-01 US
Categories
- ATC Codes
- A16AX01 — Thioctic acid
- Drug Categories
- Alimentary Tract and Metabolism
- Antioxidants
- Biological Factors
- Coenzymes
- Compounds used in a research, industrial, or household setting
- Dietary Supplements
- Enzymes and Coenzymes
- Fatty Acids
- Hypoglycemia-Associated Agents
- Lipids
- Micronutrients
- Protective Agents
- Sulfur Compounds
- Supplements
- Thiophenes
- Various Alimentary Tract and Metabolism Products
- Vitamin B Complex
- Vitamins
- 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
- Perham RN: Swinging arms and swinging domains in multifunctional enzymes: catalytic machines for multistep reactions. Annu Rev Biochem. 2000;69:961-1004. [Article]
- 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]
- 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]
- 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]
- MS Society Canada: Lipoic Acid [Link]
- External Links
- Human Metabolome Database
- HMDB0001451
- KEGG Drug
- D00086
- KEGG Compound
- C16241
- PubChem Compound
- 6112
- PubChem Substance
- 46504826
- ChemSpider
- 5886
- BindingDB
- 50106731
- 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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Impaired Glucose Tolerance / Type 2 Diabetes Mellitus 1 4 Completed Prevention Anti Oxidative Stress / End Stage Renal Disease, Requiring Dialysis 1 4 Completed Prevention Coronary Artery Disease (CAD) / Left Ventricular Mass / Type 2 Diabetes Mellitus 1 4 Completed Prevention Migraine in Adolescents 1 4 Completed Treatment Cardiac Autonomic Neuropathy / Type 2 Diabetes Mellitus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Freeda Vitamins
- Mason Distributors
- Spectrum Pharmaceuticals
- Sundown Inc.
- Tyler Encapsulations
- Dosage Forms
Form Route Strength Solution Intravenous 60000000 mg Tablet, extended release Oral Capsule Oral Solution Parenteral 600 MG Injection, solution Parenteral 600 MG Capsule Oral 300 MG Capsule Oral 600 MG Tablet, delayed release Oral Tablet, film coated Oral 600 mg/1 Tablet, coated Oral Tablet Oral Capsule Oral 100 mg Injection, solution 600 mg/50ml Injection, solution Capsule Oral 50 mg Tablet, film coated Oral 60000000 mg Tablet, coated Oral 300 mg Capsule Oral Tablet, film coated Oral Cream Topical Tablet Oral 600 mg Capsule, liquid filled Oral Tablet, film coated Oral 200 mg Tablet Oral 600.000 mg Injection, solution Intravenous 600 mg/24ml Injection, solution Intravenous 600 mg/50ml Solution Intravenous 600.000 mg Injection, solution Intravenous Injection, solution Intravenous 600 mg Tablet, film coated Oral 600 mg Tablet, coated Oral 600 mg Solution Intravenous 600 mg Lotion Topical Capsule, gelatin coated Oral - Prices
Unit description Cost Unit Lipoic acid powder 77.35USD g Lipoic acid capsule 0.26USD capsule Alpha lipoic acid 200 mg tablet 0.22USD tablet Alpha-lipoic acid 50 mg caplet 0.16USD caplet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 60.5 °C PhysProp boiling point (°C) 162.5 °C PhysProp water solubility Insoluble Not Available logP 2.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.224 mg/mL ALOGPS logP 2.75 ALOGPS logP 2.11 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 4.52 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 54.37 m3·mol-1 Chemaxon Polarizability 21.74 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9695 Blood Brain Barrier + 0.9749 Caco-2 permeable - 0.5385 P-glycoprotein substrate Non-substrate 0.7248 P-glycoprotein inhibitor I Non-inhibitor 0.9526 P-glycoprotein inhibitor II Non-inhibitor 0.9856 Renal organic cation transporter Non-inhibitor 0.8373 CYP450 2C9 substrate Non-substrate 0.7961 CYP450 2D6 substrate Non-substrate 0.8334 CYP450 3A4 substrate Non-substrate 0.7346 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9365 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9301 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.8721 Biodegradation Ready biodegradable 0.7788 Rat acute toxicity 2.2921 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9452 hERG inhibition (predictor II) Non-inhibitor 0.9451
Spectra
- Mass Spec (NIST)
- Download (11.4 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 147.9945289 predictedDarkChem Lite v0.1.0 [M-H]- 147.0469289 predictedDarkChem Lite v0.1.0 [M-H]- 147.0686289 predictedDarkChem Lite v0.1.0 [M-H]- 148.0634289 predictedDarkChem Lite v0.1.0 [M-H]- 139.93855 predictedDeepCCS 1.0 (2019) [M+H]+ 142.33412 predictedDeepCCS 1.0 (2019) [M+Na]+ 149.63976 predictedDeepCCS 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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]
- 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]
- 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
- 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]
- 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]
- 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