Explore a selection of our essential drug information below, or:
Identification
- Summary
Niacin is a B vitamin used to treat hypertriglyceridemia and pellagra.
- Brand Names
- Advicor, Concept Ob, Irospan 24/6 Kit, Mvc-fluoride, Niacor, Niaspan, Niodan, Simcor, Vitafol-one
- Generic Name
- Niacin
- DrugBank Accession Number
- DB00627
- Background
Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions.6,7,8,9,10,11
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical
- Structure
Structure for Niacin (DB00627)
- Weight
- Average: 123.1094
Monoisotopic: 123.032028409 - Chemical Formula
- C6H5NO2
- Synonyms
- 3-carboxypyridine
- 3-Pyridinecarboxylic acid
- 3-Pyridylcarboxylic acid
- Acide nicotinique
- ácido nicotínico
- Acidum Nicotinicum
- anti-pellagra vitamin
- m-pyridinecarboxylic acid
- Niacin
- Niacina
- Nicotinic acid
- Nikotinsäure
- pyridine-β-carboxylic acid
- β-pyridinecarboxylic acid
- External IDs
- NSC-169454
Pharmacology
- Indication
Niacin is indicated to prevent vitamin deficiencies in pediatric and adult patients receiving parenteral nutrition as part of multivitamin intravenous injections.6,7,8,9 Niacin oral tablets are indicated as a monotherapy or in combination with simvastatin or lovastatin to treat primary hyperlipidemia and mixed dyslipidemia.10,11 It can also be used to reduce the risk of nonfatal myocardial infarctions in patients with a history of myocardial infarction and hyperlipidemia.10,11 Niacin is also indicated with bile acid binding resins to treat atherosclerosis in patients with coronary artery disease and hyperlipidemia or to treat primary hyperlipidemia.10,11 Finally niacin is indicated to treat severe hypertriglyceridemia.10,11
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 to manage Atherosclerotic disease •••••••••••• •••••••••••••••• ••••••• •• •••••••• •••••• ••••••• ••••••• •••••••• ••••••• Used as adjunct in combination to manage High cholesterol Combination Product in combination with: Lovastatin (DB00227) •••••••••••• •••••••• ••• •••• ••••••••••• ••••••• •• ••••••••••• ••••••• •••••••• ••••••• Adjunct therapy in management of High triglyceride level •••••••••••• ••••• •••• •••••••••••••• •••• •••••• Adjunct therapy in management of Mixed dyslipidemias •••••••••••• ••••••• •••••••• ••••••• Prevention of Nonfatal myocardial infarction •••••••••••• ••••••• •• •••••••••• ••••••••••• •••• ••••••••••• ••••••• •••••••• ••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Niacin is a B vitamin used to treat vitamin deficiencies as well as hyperlipidemia, dyslipidemia, hypertriglyceridemia, and to reduce the risk of myocardial infarctions.6,7,8,9,10,11 Niacin acts to decrease levels of very low density lipoproteins and low density lipoproteins, while increasing levels of high density lipoproteins.3 Niacin has a wide therapeutic window with usual oral doses between 500mg and 2000mg.6 Patients with diabetes, renal failure, uncontrolled hypothyroidism, and elderly patients taking niacin with simvastatin or lovastatin are at increased risk of myopathy and rhabdomyolysis.6
- Mechanism of action
Niacin performs a number of functions in the body and so has many mechanisms, not all of which have been fully described.3 Niacin can decrease lipids and apolipoprotein B (apo B)-containing lipoproteins by modulating triglyceride synthesis in the liver, which degrades apo B, or by modulating lipolysis in adipose tissue.3
Niacin inhibits hepatocyte diacylglycerol acyltransferase-2.3 This action prevents the final step of triglyceride synthesis in hepatocytes, limiting available triglycerides for very low density lipoproteins (VLDL).3 This activity also leads to intracellular degradation of apo B and decreased production of low density lipoproteins, the catabolic product of VLDL.3
Niacin also inhibits a high density lipoprotein (HDL) catabolism receptor, which increases the levels and half life of HDL.3
Target Actions Organism AHydroxycarboxylic acid receptor 3 agonistHumans ADiacylglycerol O-acyltransferase 2 inhibitorHumans AHydroxycarboxylic acid receptor 2 agonistHumans ANicotinate-nucleotide pyrophosphorylase [carboxylating] binderHumans ANicotinamide N-methyltransferase binderHumans - Absorption
In patients with chronic kidney disease, the Cmax is 0.06µg/mL for a 500mg oral dose, 2.42µg/mL for a 1000mg oral dose, and 4.22µg/mL for a 1500mg oral dose.2 The Tmax is 3.0 hours for a 1000mg or 1500mg oral dose.2 The AUC is 1.44µg*h/mL for a 500mg oral dose, 6.66µg*h/mL for a 1000mg oral dose, and 12.41µg*h/mL for a 1500mg oral dose.2 These values did not drastically differ in patients requiring dialysis.2
- Volume of distribution
Data regarding the volume of distribution of niacin is not readily available.
- Protein binding
Data regarding the protein binding of niacin is not readily available.
- Metabolism
The metabolism of niacin is poorly described in the literature, but the metabolites niacinamide, niacinamide N-oxide, nicotinuric acid, N1-methyl-2-pyridone-5-carboxamide, N1-methyl-4-pyridone-5-carboxamide, and trigonelline have been identified in human urine.4
Hover over products below to view reaction partners
- Route of elimination
69.5% of a dose of niacin is recovered in urine.5 37.9% of the recovered dose was N-methyl-2-pyridone-5-carboxamide, 16.0% was N-methylnicotinamide, 11.6% was nicotinuric acid, and 3.2% was niacin.5
- Half-life
The half life of niacin is 0.9h, nicotinuric acid is 1.3h, and nicotinamide is 4.3h.5
- Clearance
Data regarding the clearance of niacin is not readily available.
- Adverse Effects
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Overdose of niacin may present with severe prolonged hypotension.1 Patients experiencing an overdose should be treated with supportive measures which may include intravenous fluids.1,6
The oral LD50 in the mouse is 3720mg/kg, in the rabbit is 4550mg/kg, in the rat is 7000mg/kg, and the dermal LD50 in the rat is >2000mg/kg.12
- Pathways
Pathway Category Nicotinate and Nicotinamide Metabolism Metabolic - 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Niacin. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is combined with Niacin. Acarbose The therapeutic efficacy of Acarbose can be decreased when used in combination with Niacin. Acebutolol The metabolism of Acebutolol can be decreased when combined with Niacin. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Niacin. - Food Interactions
- Avoid alcohol. Alcohol increases the chance of flushing and pruritus.
- Take with food. Food reduces gastrointestinal upset and irritation.
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.- Active Moieties
Name Kind UNII CAS InChI Key Nicotinamide unknown 25X51I8RD4 98-92-0 DFPAKSUCGFBDDF-UHFFFAOYSA-N - Product Images
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image B-3 500mg Continuous Released Tablet, extended release 500 mg Oral Gahler Enterprises Ltd. 1981-12-31 2000-08-01 Canada 
Niacin Tablet, film coated, extended release 1000 mg/1 Oral Zydus Pharmaceuticals USA Inc 2014-06-30 2019-07-13 US 
Niacin Tablet, film coated, extended release 750 mg/1 Oral Zydus Pharmaceuticals USA Inc 2014-06-30 2018-12-01 US Niacin Tablet, film coated, extended release 500 mg/1 Oral Zydus Pharmaceuticals USA Inc 2014-06-30 2019-07-09 US Niacin Ctr Srt 500mg Tablet, extended release 500 mg / tab Oral Bioenergy Inc. 1981-12-31 1998-06-03 Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Niacin Tablet, film coated, extended release 750 mg/1 Oral Amneal Pharmaceuticals LLC 2015-12-11 Not applicable US Niacin Tablet, film coated, extended release 500 mg/1 Oral Yichang Humanwell Pharmaceutical Co., Ltd 2021-04-20 2021-04-20 US Niacin Tablet, extended release 500 mg/1 Oral AvPAK 2017-09-14 Not applicable US Niacin Tablet, extended release 500 mg/1 Oral Lupin Pharmaceuticals, Inc. 2014-03-20 2023-09-30 US 
Niacin Tablet, film coated, extended release 500 mg/1 Oral Avera McKennan Hospital 2015-10-14 2017-05-24 US 
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Acti-niacin Caplet 500mg Tablet 500 mg Oral Acti Form Ltd. 1991-12-31 2005-03-21 Canada B3 Tablet 500 mg Oral Natural Factors Nutritional Products Ltd. 1997-12-30 2008-07-17 Canada Formula # 7 Tab 50mg Tablet 50 mg Oral Golden Pride/Rawleigh 1995-12-31 2004-10-15 Canada JEUNCELL Hair restorer and Hair Growth Solution Shampoo 2 mg/100mL Topical Jeun Cell Ltd 2012-11-25 Not applicable US Niacin 100 mg Capsule 100 mg Oral Flora Manufacturing And Distributing Ltd. 2002-03-15 2004-08-04 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 24 Multivitamins + Minerals Niacin (25 mg) + Ascorbic acid (150 mg) + Beta carotene (10000 unit) + Biotin (25 mcg) + Calcium (130 mg) + Cholecalciferol (400 unit) + Choline bitartrate (25 mg) + Chromium (20 mcg) + Copper (1 mg) + Cyanocobalamin (25 mcg) + Ferrous fumarate (15 mg) + Folic acid (.8 mg) + Inositol (25 mg) + Magnesium (65 mg) + Manganese cation (2 mg) + Molybdenum (20 mcg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (25 mg) + Riboflavin (25 mg) + Selenium (20 mcg) + Thiamine hydrochloride (25 mg) + Vanadium (20 mcg) + Vitamin A palmitate (5000 unit) + Vitamin E (50 unit) + Zinc (10 mg) Tablet Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1997-04-30 2002-07-31 Canada 4Life Targeted Vitamin & Mineral Complex Capsule Niacin (5 mg) + Ascorbic acid (50.76 mg) + Beta carotene (630 IU) + Chromium (0.07 mg) + Copper (0.5 mg) + Cyanocobalamin (0.002 mg) + Folic acid (0.1 mg) + Magnesium (46.4 mg) + Potassium (12.5 mg) + Pyridoxine (0.5 mg) + Selenium (0.013 mg) + Vanadium (0.15 mg) + Vitamin E (25.5 IU) + Zinc (2.5 mg) Capsule Oral Forlife Research Imports Sdn. Bhd. 2020-09-08 Not applicable Malaysia 
50 Plus Niacin (20 mg) + Ascorbic acid (200 mg) + Biotin (20 mcg) + Choline bitartrate (20 mg) + Cyanocobalamin (20 mcg) + Folic acid (.2 mg) + Inositol (20 mg) + Calcium pantothenate (20 mg) + Pyridoxine hydrochloride (20 mg) + Racemethionine (20 mg) + Riboflavin (20 mg) + Thiamine hydrochloride (20 mg) + Vitamin A palmitate (10000 unit) + Vitamin D (400 unit) + Vitamin E (20 unit) Tablet Oral Quest Vitamins A Div Of Purity Life Health Products 1998-08-04 2001-07-06 Canada ActiveLife ALA Plus Capsule Niacin (10 mg) + Chromium picolinate (0.2 mg) + Folic acid (0.5 mg) + Lipoic acid (150 mg) + Mecobalamin (0.15 mg) + Pyridoxine hydrochloride (60 mg) + Riboflavin (3.5 mg) + Thiamine hydrochloride (60 mg) Capsule Oral HS Health Serve Sdn. Bhd. 2020-09-08 2020-12-17 Malaysia Adeks Tablets Niacin (10 mg) + Ascorbic acid (60 mg) + Beta carotene (3 mg) + Biotin (50 mcg) + Cholecalciferol (400 unit) + Cyanocobalamin (12 mcg) + Folic acid (0.2 mg) + Calcium pantothenate (10 mg) + Phylloquinone (0.15 mg) + Pyridoxine (1.5 mg) + Riboflavin (1.3 mg) + Thiamine (1.2 mg) + Vitamin A palmitate (4000 unit) + Vitamin E (150 unit) + Zinc gluconate (7.5 mg) Tablet Oral Axcan Pharma 1998-01-20 2011-04-20 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Abavite Niacin (15 mg/1) + Ascorbic acid (60 mg/1) + Cholecalciferol (0.025 mg/1) + DL-alpha tocopheryl acetate (13.5 mg/1) + Ferrous sulfate (30 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (25 mg/1) + Mecobalamin (0.5 mg/1) + Calcium pantothenate (5 mg/1) + Potassium Iodide (0.25 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Vitamin A palmitate (0.33 mg/1) + Zinc oxide (15 mg/1) Tablet Oral ABACOS HEALTH 2021-03-31 Not applicable US Cavan Heme OB Niacin (17 mg/1) + Biotin (30 ug/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (0.8 mg/1) + Cyanocobalamin (12 ug/1) + Folic acid (1 mg/1) + Iron (28 mg/1) + Calcium pantothenate (10 mg/1) + Potassium Iodide (175 ug/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (1.6 mg/1) + Sodium selenate (65 ug/1) + Thiamine mononitrate (1.5 mg/1) + Zinc oxide (15 mg/1) + alpha-Tocopherol succinate (10 [iU]/1) Tablet Oral Seton Pharmaceuticals 2010-08-03 2012-06-10 US Cavan Prenatal Niacin (20 mg/1) + Ascorbic acid (120 mg/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (420 [iU]/1) + Choline bitartrate (55 mg/1) + Cyanocobalamin (8 ug/1) + Ferrous fumarate (28 mg/1) + Folic acid (1 mg/1) + Potassium Iodide (150 ug/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (3 mg/1) + Thiamine mononitrate (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc oxide (15 ug/1) Tablet Oral Seton Pharmaceuticals 2009-07-09 2009-07-22 US Concept DHA Niacin (1.8 mg/1) + Ascorbic acid (25 mg/1) + Biotin (300 ug/1) + Cupric sulfate pentahydrate (2 mg/1) + Cyanocobalamin (12.5 ug/1) + Ferrous fumarate (17.5 mg/1) + Folic acid (1 mg/1) + Iron (17.5 mg/1) + Magnesium sulfate (5 mg/1) + Omega-3-acid ethyl esters (200 mg/1) + Calcium pantothenate (5 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc sulfate, unspecified form (10 mg/1) Capsule, liquid filled Oral U.S. Pharmaceutical Corporation 2009-06-24 Not applicable US Concept OB Niacin (20 mg/1) + Ascorbic acid (210 mg/1) + Biotin (300 ug/1) + Cupric sulfate pentahydrate (800 ug/1) + Cyanocobalamin (10 ug/1) + Ferrous fumarate (42.5 mg/1) + Folic acid (1 mg/1) + Iron (42.5 mg/1) + Magnesium sulfate (6.9 mg/1) + Manganese sulfate (1.3 mg/1) + Calcium pantothenate (7 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (5 mg/1) + Thiamine mononitrate (5 mg/1) + Zinc sulfate, unspecified form (18.2 mg/1) Capsule Oral U.S. Pharmaceutical Corporation 2009-01-01 Not applicable US
Categories
- ATC Codes
- C10AD02 — Nicotinic acid
- C10AD — Nicotinic acid and derivatives
- C10A — LIPID MODIFYING AGENTS, PLAIN
- C10 — LIPID MODIFYING AGENTS
- C — CARDIOVASCULAR SYSTEM
- C10AD — Nicotinic acid and derivatives
- C10A — LIPID MODIFYING AGENTS, PLAIN
- C10 — LIPID MODIFYING AGENTS
- C — CARDIOVASCULAR SYSTEM
- C10BA — Combinations of various lipid modifying agents
- C10B — LIPID MODIFYING AGENTS, COMBINATIONS
- C10 — LIPID MODIFYING AGENTS
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Agents Causing Muscle Toxicity
- Cardiovascular Agents
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2E1 Inhibitors
- Cytochrome P-450 CYP2E1 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Diet, Food, and Nutrition
- Food
- Growth Substances
- Hyperglycemia-Associated Agents
- Hypolipidemic Agents
- Hypolipidemic Agents Indicated for Hyperlipidemia
- Lipid Modifying Agents
- Lipid Modifying Agents, Plain
- Lipid Regulating Agents
- Micronutrients
- Miscellaneous Antilipemic Agents
- Nicotinic Acid and Derivatives
- Nicotinic Acids
- Non-statin Hypolipidemic Agents Indicated for Hyperlipidemia
- Noxae
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Peripheral Vasodilators
- Physiological Phenomena
- Pyridines
- Thyroxine-binding globulin inhibitors
- Toxic Actions
- Vasodilating Agents
- Vitamin B Complex
- Vitamins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as pyridinecarboxylic acids. These are compounds containing a pyridine ring bearing a carboxylic acid group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyridines and derivatives
- Sub Class
- Pyridinecarboxylic acids and derivatives
- Direct Parent
- Pyridinecarboxylic acids
- Alternative Parents
- Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound / Organic oxide / Organic oxygen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyridine alkaloid, pyridinemonocarboxylic acid (CHEBI:15940) / Water-soluble vitamins, Pyridine alkaloids (C00253)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 2679MF687A
- CAS number
- 59-67-6
- InChI Key
- PVNIIMVLHYAWGP-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
- IUPAC Name
- pyridine-3-carboxylic acid
- SMILES
- OC(=O)C1=CN=CC=C1
References
- Synthesis Reference
Joseph E. Toomey, Jr., "Electrochemical synthesis of niacin and other N-heterocyclic compounds." U.S. Patent US5002641, issued 1914.
US5002641- General References
- Mularski RA, Grazer RE, Santoni L, Strother JS, Bizovi KE: Treatment advice on the internet leads to a life-threatening adverse reaction: hypotension associated with Niacin overdose. Clin Toxicol (Phila). 2006;44(1):81-4. [Article]
- Reiche I, Westphal S, Martens-Lobenhoffer J, Troger U, Luley C, Bode-Boger SM: Pharmacokinetics and dose recommendations of Niaspan(R) in chronic kidney disease and dialysis patients. Nephrol Dial Transplant. 2011 Jan;26(1):276-82. doi: 10.1093/ndt/gfq344. Epub 2010 Jun 17. [Article]
- Kamanna VS, Kashyap ML: Mechanism of action of niacin. Am J Cardiol. 2008 Apr 17;101(8A):20B-26B. doi: 10.1016/j.amjcard.2008.02.029. [Article]
- Taguchi K, Fukusaki E, Bamba T: Determination of niacin and its metabolites using supercritical fluid chromatography coupled to tandem mass spectrometry. Mass Spectrom (Tokyo). 2014;3(1):A0029. doi: 10.5702/massspectrometry.A0029. Epub 2014 Aug 1. [Article]
- Menon RM, Adams MH, Gonzalez MA, Tolbert DS, Leu JH, Cefali EA: Plasma and urine pharmacokinetics of niacin and its metabolites from an extended-release niacin formulation. Int J Clin Pharmacol Ther. 2007 Aug;45(8):448-54. doi: 10.5414/cpp45448. [Article]
- FDA Approved Drug Products: Niacin Film Coated Extended Release Tablets [Link]
- FDA Approved Drug Products: Niacin Oral Tablet [Link]
- FDA Approved Drug Products: M.V.I. Pediatric Multivitamin Intravenous Injection [Link]
- FDA Approved Drug Products: Infuvite Pediatric Multivitamin Intravenous Injection [Link]
- FDA Approved Drug Products: Infuvite Adult Multivitamin Intravenous Injection [Link]
- FDA Approved Drug Products: M.V.I. Adult Multivitamin Intravenous Injection [Link]
- Jubilant Life Sciences: Niacin MSDS [Link]
- DailyMed: Niacin Oral Tablet, Extended Release [Link]
- External Links
- Human Metabolome Database
- HMDB0001488
- KEGG Drug
- D00049
- KEGG Compound
- C00253
- PubChem Compound
- 938
- PubChem Substance
- 46507508
- ChemSpider
- 913
- BindingDB
- 23515
- 7393
- ChEBI
- 15940
- ChEMBL
- CHEMBL573
- ZINC
- ZINC000000001795
- PharmGKB
- PA450617
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- NIO
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Niacin
- PDB Entries
- 1d0v / 1fsl / 1icr / 1icu / 1icv / 1jha / 1jho / 1jhq / 1jhr / 1jhv … show 61 more
- FDA label
- Download (330 KB)
- MSDS
- Download (73.2 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Not Available Dyslipoproteinemias 1 somestatus stop reason just information to hide Not Available Completed Not Available Atherosclerosis / Cardiovascular Disease (CVD) / Coronary Heart Disease (CHD) / Myocardial Infarction 1 somestatus stop reason just information to hide Not Available Completed Not Available Atherosclerosis / Carotid Artery Diseases / Coronary Artery Disease (CAD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Cardiovascular Disease (CVD) 1 somestatus stop reason just information to hide Not Available Completed Not Available Carotid Artery Diseases / Coronary Artery Disease (CAD) / Peripheral Arterial Disease (PAD) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Medpointe pharmaceuticals medpointe healthcare inc
- Barr laboratories inc
- Abbott laboratories
- Everylife
- Halsey drug co inc
- Impax laboratories inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Mk laboratories inc
- Purepac pharmaceutical co
- Sandoz inc
- Tablicaps inc
- Watson laboratories inc
- West ward pharmaceutical corp
- Wockhardt ltd
- Upsher smith laboratories inc
- Sanofi aventis us llc
- Packagers
- Abbott Laboratories Ltd.
- Aeropharm Technology LLC
- Amend
- Apothecon
- A-S Medication Solutions LLC
- Bronson Pharmaceuticals
- Catalent Pharma Solutions
- Contract Pharm
- CVS Pharmacy
- Ide Interstate
- Ivax Pharmaceuticals
- Major Pharmaceuticals
- Mason Distributors
- Murfreesboro Pharmaceutical Nursing Supply
- National Vitamin Company
- Norwich Pharmaceuticals Inc.
- Physicians Total Care Inc.
- Prepak Systems Inc.
- Rugby Laboratories
- Sepracor Pharmaceuticals Inc.
- Sirius Labs
- Southwood Pharmaceuticals
- Spectrum Pharmaceuticals
- Upsher Smith Laboratories
- US Pharmaceutical Corp.
- Va Cmop Dallas
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Tablet Oral 500 mg Tablet, extended release Oral Tablet, extended release; tablet, multilayer, extended release Oral Solution Intramuscular; Intravenous Tablet, film coated Tablet Oral 50 mg Tablet, film coated Oral Tablet Oral 100.0 mg Kit; tablet; tablet, film coated Oral Shampoo Topical 2 mg/100mL Solution / drops Oral Solution Oral Tablet Oral Tablet Oral Tablet, orally disintegrating Oral Capsule, gelatin coated; kit; tablet Oral Capsule, extended release Oral 250 mg/1 Capsule, extended release Oral 500 mg/1 Tablet Oral 1000 mg/1 Tablet Oral 500 mg/1 Tablet, extended release Oral 1000 mg/1 Tablet, extended release Oral 500 mg/1 Tablet, extended release Oral 750 mg/1 Capsule Oral 100 mg Capsule Oral 250 mg / cap Capsule Oral 100 mg / cap Tablet, extended release Oral 500 mg / tab Solution Intramuscular; Intravenous 100 mg / mL Powder Oral 800 mg / 1.25 mL Capsule, extended release Oral 400 mg / cap Tablet Oral 100 mg / tab Tablet Oral 250 mg / tab Tablet, extended release Oral 475 mg / tab Tablet Oral 500 mg / tab Tablet Oral 1000 mg Tablet, extended release Oral 750 mg Tablet, film coated, extended release Oral 1000 mg/1 Tablet, film coated, extended release Oral 500 mg/1 Tablet, film coated, extended release Oral 750 mg/1 Tablet, extended release Oral 375 mg Tablet, delayed release Oral 1000 mg Tablet, delayed release Oral 500 mg Tablet, extended release Oral 1000 mg Tablet, extended release Oral Tablet, extended release Oral 500 mg Liquid Oral Gum, chewing Oral Capsule, coated Oral Capsule, liquid filled; kit; tablet Oral Capsule, gelatin coated Oral Tablet, chewable Oral Tablet, film coated, extended release Oral Tablet, coated Oral Tablet, extended release Oral 500 mg / srt Lozenge Oral Capsule, extended release Oral 300 mg / cap Capsule Oral Capsule, liquid filled; kit Oral Capsule, liquid filled Oral Capsule; kit; tablet, coated Oral Tablet Oral 10 mg / tab Kit Oral Powder Oral Tablet Oral 250 mg Tablet, coated Oral 50 mg Tablet Oral 100 mg - Prices
Unit description Cost Unit Niaspan 1000 mg Controlled Release Tabs 4.67USD tab Simcor 1000-20 mg 24 Hour tablet 4.67USD tablet Niaspan er 1000 mg tablet 4.49USD tablet Simcor 1000-20 mg tablet 4.49USD tablet Niaspan 1000 mg tablet er 4.04USD tablet Niaspan 750 mg Controlled Release Tabs 3.76USD tab Niaspan er 750 mg tablet 3.62USD tablet Simcor 750-20 mg tablet 3.62USD tablet Niaspan 750 mg tablet er 3.25USD tablet Niaspan 500 mg Controlled Release Tabs 2.65USD tab Simcor 500-20 mg 24 Hour tablet 2.64USD tablet Niaspan er 500 mg tablet 2.54USD tablet Simcor 500-20 mg tablet 2.54USD tablet Niaspan 500 mg tablet er 2.28USD tablet Nicomide-t 4% cream 1.1USD g Niacinamide ascorbate powder 0.57USD g Niacin flush free 750 mg capsule 0.35USD capsule Niacinamide powder 0.24USD g Slo-niacin 750 mg tablet 0.19USD tablet Niacin 500 mg capsule 0.16USD capsule Slo-niacin 500 mg tablet 0.14USD tablet Niacin 500 mg tablet 0.1USD tablet Slo-niacin 250 mg tablet 0.09USD tablet Niacin 1000 mg tablet sa 0.08USD tablet No flush niacin capsule 0.08USD capsule Niacin 250 mg tablet sa 0.06USD tablet Niacin flush free 500 mg capsule 0.06USD capsule Niacin 250 mg tablet 0.03USD tablet Niacinamide 500 mg tablet 0.03USD tablet Niacin 100 mg caplet 0.02USD caplet Niacin 100 mg tablet 0.02USD tablet Niacin 50 mg tablet 0.02USD tablet Niacinamide 100 mg tablet 0.02USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6129930 No 2000-10-10 2013-09-20 US CA2283159 No 2007-06-19 2018-03-06 Canada CA2298549 No 2006-01-10 2018-07-31 Canada US6080428 No 2000-06-27 2017-05-27 US US6469035 No 2002-10-22 2018-03-15 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 236-239 http://www.chemspider.com/Chemical-Structure.913.html?rid=9af4dd1d-a79e-4e6d-ab2a-9fe7ca6a3248 boiling point (°C) 292.4 http://www.chemspider.com/Chemical-Structure.913.html?rid=9af4dd1d-a79e-4e6d-ab2a-9fe7ca6a3248 water solubility 1.8E+004 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 0.147 http://www.chemspider.com/Chemical-Structure.913.html?rid=9af4dd1d-a79e-4e6d-ab2a-9fe7ca6a3248 logS -0.84 ADME Research, USCD pKa 4.75 (at 25 °C) DEAN,JA (1985) - Predicted Properties
Property Value Source Water Solubility 83.1 mg/mL ALOGPS logP 0.29 ALOGPS logP -0.17 Chemaxon logS -0.17 ALOGPS pKa (Strongest Acidic) 2.79 Chemaxon pKa (Strongest Basic) 4.19 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 50.19 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 31.16 m3·mol-1 Chemaxon Polarizability 11.3 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9672 Blood Brain Barrier + 0.9648 Caco-2 permeable + 0.8701 P-glycoprotein substrate Non-substrate 0.8683 P-glycoprotein inhibitor I Non-inhibitor 0.9935 P-glycoprotein inhibitor II Non-inhibitor 1.0 Renal organic cation transporter Non-inhibitor 0.8938 CYP450 2C9 substrate Non-substrate 0.8246 CYP450 2D6 substrate Non-substrate 0.9231 CYP450 3A4 substrate Non-substrate 0.8381 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.94 CYP450 3A4 inhibitor Non-inhibitor 0.912 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9875 Ames test Non AMES toxic 0.9939 Carcinogenicity Non-carcinogens 0.8566 Biodegradation Ready biodegradable 0.9437 Rat acute toxicity 1.2760 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9557 hERG inhibition (predictor II) Non-inhibitor 0.9829
Spectra
- Mass Spec (NIST)
- Download (7.87 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 120.6446436 predictedDarkChem Lite v0.1.0 [M-H]- 120.6650436 predictedDarkChem Lite v0.1.0 [M-H]- 120.7029436 predictedDarkChem Lite v0.1.0 [M-H]- 120.5824436 predictedDarkChem Lite v0.1.0 [M-H]- 121.40254 predictedDeepCCS 1.0 (2019) [M+H]+ 121.4199436 predictedDarkChem Lite v0.1.0 [M+H]+ 128.3529137 predictedDarkChem Standard v0.1.0 [M+H]+ 121.4649436 predictedDarkChem Lite v0.1.0 [M+H]+ 121.4078436 predictedDarkChem Lite v0.1.0 [M+H]+ 124.65425 predictedDeepCCS 1.0 (2019) [M+Na]+ 120.7980436 predictedDarkChem Lite v0.1.0 [M+Na]+ 120.9003436 predictedDarkChem Lite v0.1.0 [M+Na]+ 120.8548436 predictedDarkChem Lite v0.1.0 [M+Na]+ 120.8875436 predictedDarkChem Lite v0.1.0 [M+Na]+ 133.4807 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor for 3-OH-octanoid acid mediates a negative feedback regulation of adipocyte lipolysis to counteract prolipolytic influences under conditions of physiological or pathological increases in beta-oxidation rates. Acts as a low affinity receptor for nicotinic acid. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet
- Specific Function
- G protein-coupled receptor activity
- Gene Name
- HCAR3
- Uniprot ID
- P49019
- Uniprot Name
- Hydroxycarboxylic acid receptor 3
- Molecular Weight
- 44477.93 Da
References
- Tunaru S, Kero J, Schaub A, Wufka C, Blaukat A, Pfeffer K, Offermanns S: PUMA-G and HM74 are receptors for nicotinic acid and mediate its anti-lipolytic effect. Nat Med. 2003 Mar;9(3):352-5. Epub 2003 Feb 3. [Article]
- Taggart AK, Kero J, Gan X, Cai TQ, Cheng K, Ippolito M, Ren N, Kaplan R, Wu K, Wu TJ, Jin L, Liaw C, Chen R, Richman J, Connolly D, Offermanns S, Wright SD, Waters MG: (D)-beta-Hydroxybutyrate inhibits adipocyte lipolysis via the nicotinic acid receptor PUMA-G. J Biol Chem. 2005 Jul 22;280(29):26649-52. Epub 2005 Jun 1. [Article]
- Zhang Y, Schmidt RJ, Foxworthy P, Emkey R, Oler JK, Large TH, Wang H, Su EW, Mosior MK, Eacho PI, Cao G: Niacin mediates lipolysis in adipose tissue through its G-protein coupled receptor HM74A. Biochem Biophys Res Commun. 2005 Aug 26;334(2):729-32. [Article]
- Tunaru S, Lattig J, Kero J, Krause G, Offermanns S: Characterization of determinants of ligand binding to the nicotinic acid receptor GPR109A (HM74A/PUMA-G). Mol Pharmacol. 2005 Nov;68(5):1271-80. Epub 2005 Aug 11. [Article]
- Benyo Z, Gille A, Kero J, Csiky M, Suchankova MC, Nusing RM, Moers A, Pfeffer K, Offermanns S: GPR109A (PUMA-G/HM74A) mediates nicotinic acid-induced flushing. J Clin Invest. 2005 Dec;115(12):3634-40. [Article]
- Wise A, Foord SM, Fraser NJ, Barnes AA, Elshourbagy N, Eilert M, Ignar DM, Murdock PR, Steplewski K, Green A, Brown AJ, Dowell SJ, Szekeres PG, Hassall DG, Marshall FH, Wilson S, Pike NB: Molecular identification of high and low affinity receptors for nicotinic acid. J Biol Chem. 2003 Mar 14;278(11):9869-74. Epub 2003 Jan 9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Essential acyltransferase that catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for synthesis and storage of intracellular triglycerides (PubMed:27184406). Probably plays a central role in cytosolic lipid accumulation. In liver, is primarily responsible for incorporating endogenously synthesized fatty acids into triglycerides (By similarity). Functions also as an acyl-CoA retinol acyltransferase (ARAT) (By similarity). Also able to use 1-monoalkylglycerol (1-MAkG) as an acyl acceptor for the synthesis of monoalkyl-monoacylglycerol (MAMAG) (PubMed:28420705)
- Specific Function
- 2-acylglycerol o-acyltransferase activity
- Gene Name
- DGAT2
- Uniprot ID
- Q96PD7
- Uniprot Name
- Diacylglycerol O-acyltransferase 2
- Molecular Weight
- 43830.475 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Acts as a high affinity receptor for both nicotinic acid (also known as niacin) and (D)-beta-hydroxybutyrate and mediates increased adiponectin secretion and decreased lipolysis through G(i)-protein-mediated inhibition of adenylyl cyclase. This pharmacological effect requires nicotinic acid doses that are much higher than those provided by a normal diet. Mediates nicotinic acid-induced apoptosis in mature neutrophils. Receptor activation by nicotinic acid results in reduced cAMP levels which may affect activity of cAMP-dependent protein kinase A and phosphorylation of target proteins, leading to neutrophil apoptosis. The rank order of potency for the displacement of nicotinic acid binding is 5-methyl pyrazole-3-carboxylic acid = pyridine-3-acetic acid > acifran > 5-methyl nicotinic acid = acipimox >> nicotinuric acid = nicotinamide
- Specific Function
- Nicotinic acid receptor activity
- Gene Name
- HCAR2
- Uniprot ID
- Q8TDS4
- Uniprot Name
- Hydroxycarboxylic acid receptor 2
- Molecular Weight
- 41849.08 Da
References
- Wise A, Foord SM, Fraser NJ, Barnes AA, Elshourbagy N, Eilert M, Ignar DM, Murdock PR, Steplewski K, Green A, Brown AJ, Dowell SJ, Szekeres PG, Hassall DG, Marshall FH, Wilson S, Pike NB: Molecular identification of high and low affinity receptors for nicotinic acid. J Biol Chem. 2003 Mar 14;278(11):9869-74. Epub 2003 Jan 9. [Article]
- Soga T, Kamohara M, Takasaki J, Matsumoto S, Saito T, Ohishi T, Hiyama H, Matsuo A, Matsushime H, Furuichi K: Molecular identification of nicotinic acid receptor. Biochem Biophys Res Commun. 2003 Mar 28;303(1):364-9. [Article]
- Zellner C, Pullinger CR, Aouizerat BE, Frost PH, Kwok PY, Malloy MJ, Kane JP: Variations in human HM74 (GPR109B) and HM74A (GPR109A) niacin receptors. Hum Mutat. 2005 Jan;25(1):18-21. [Article]
- Zhang Y, Schmidt RJ, Foxworthy P, Emkey R, Oler JK, Large TH, Wang H, Su EW, Mosior MK, Eacho PI, Cao G: Niacin mediates lipolysis in adipose tissue through its G-protein coupled receptor HM74A. Biochem Biophys Res Commun. 2005 Aug 26;334(2):729-32. [Article]
- Tunaru S, Lattig J, Kero J, Krause G, Offermanns S: Characterization of determinants of ligand binding to the nicotinic acid receptor GPR109A (HM74A/PUMA-G). Mol Pharmacol. 2005 Nov;68(5):1271-80. Epub 2005 Aug 11. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Involved in the catabolism of quinolinic acid (QA)
- Specific Function
- Identical protein binding
- Gene Name
- QPRT
- Uniprot ID
- Q15274
- Uniprot Name
- Nicotinate-nucleotide pyrophosphorylase [carboxylating]
- Molecular Weight
- 30845.31 Da
References
- Fukuwatari T, Morikawa Y, Hayakawa F, Sugimoto E, Shibata K: Influence of adenine-induced renal failure on tryptophan-niacin metabolism in rats. Biosci Biotechnol Biochem. 2001 Oct;65(10):2154-61. [Article]
- Shin DH, Oganesyan N, Jancarik J, Yokota H, Kim R, Kim SH: Crystal structure of a nicotinate phosphoribosyltransferase from Thermoplasma acidophilum. J Biol Chem. 2005 May 6;280(18):18326-35. Epub 2005 Mar 6. [Article]
- Zheng XQ, Hayashibe E, Ashihara H: Changes in trigonelline (N-methylnicotinic acid) content and nicotinic acid metabolism during germination of mungbean (Phaseolus aureus) seeds. J Exp Bot. 2005 Jun;56(416):1615-23. Epub 2005 Apr 18. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Catalyzes the N-methylation of nicotinamide using the universal methyl donor S-adenosyl-L-methionine to form N1-methylnicotinamide and S-adenosyl-L-homocysteine, a predominant nicotinamide/vitamin B3 clearance pathway (PubMed:21823666, PubMed:23455543, PubMed:8182091). Plays a central role in regulating cellular methylation potential, by consuming S-adenosyl-L-methionine and limiting its availability for other methyltransferases. Actively mediates genome-wide epigenetic and transcriptional changes through hypomethylation of repressive chromatin marks, such as H3K27me3 (PubMed:23455543, PubMed:26571212, PubMed:31043742). In a developmental context, contributes to low levels of the repressive histone marks that characterize pluripotent embryonic stem cell pre-implantation state (PubMed:26571212). Acts as a metabolic regulator primarily on white adipose tissue energy expenditure as well as hepatic gluconeogenesis and cholesterol biosynthesis. In white adipocytes, regulates polyamine flux by consuming S-adenosyl-L-methionine which provides for propylamine group in polyamine biosynthesis, whereas by consuming nicotinamide controls NAD(+) levels through the salvage pathway (By similarity). Via its product N1-methylnicotinamide regulates protein acetylation in hepatocytes, by repressing the ubiquitination and increasing the stability of SIRT1 deacetylase (By similarity). Can also N-methylate other pyridines structurally related to nicotinamide and play a role in xenobiotic detoxification (PubMed:30044909)
- Specific Function
- Nicotinamide n-methyltransferase activity
- Gene Name
- NNMT
- Uniprot ID
- P40261
- Uniprot Name
- Nicotinamide N-methyltransferase
- Molecular Weight
- 29573.705 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Riederer M, Erwa W, Zimmermann R, Frank S, Zechner R: Adipose tissue as a source of nicotinamide N-methyltransferase and homocysteine. Atherosclerosis. 2009 Jun;204(2):412-7. doi: 10.1016/j.atherosclerosis.2008.09.015. Epub 2008 Sep 27. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data supporting this enzyme action are limited to the results of one in vitro study. Clinical correlation is unknown.
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
- Specific Function
- Anandamide 11,12 epoxidase activity
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Gaudineau C, Auclair K: Inhibition of human P450 enzymes by nicotinic acid and nicotinamide. Biochem Biophys Res Commun. 2004 May 7;317(3):950-6. doi: 10.1016/j.bbrc.2004.03.137. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Gaudineau C, Auclair K: Inhibition of human P450 enzymes by nicotinic acid and nicotinamide. Biochem Biophys Res Commun. 2004 May 7;317(3):950-6. doi: 10.1016/j.bbrc.2004.03.137. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of fatty acids (PubMed:10553002, PubMed:18577768). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10553002, PubMed:18577768). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids (PubMed:10553002, PubMed:18577768). May be involved in the oxidative metabolism of xenobiotics (Probable)
- Specific Function
- 4-nitrophenol 2-monooxygenase activity
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Gaudineau C, Auclair K: Inhibition of human P450 enzymes by nicotinic acid and nicotinamide. Biochem Biophys Res Commun. 2004 May 7;317(3):950-6. doi: 10.1016/j.bbrc.2004.03.137. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Major thyroid hormone transport protein in serum
- Specific Function
- Serine-type endopeptidase inhibitor activity
- Gene Name
- SERPINA7
- Uniprot ID
- P05543
- Uniprot Name
- Thyroxine-binding globulin
- Molecular Weight
- 46324.12 Da
References
- Shakir KM, Kroll S, Aprill BS, Drake AJ 3rd, Eisold JF: Nicotinic acid decreases serum thyroid hormone levels while maintaining a euthyroid state. Mayo Clin Proc. 1995 Jun;70(6):556-8. doi: 10.4065/70.6.556. [Article]
- O'Brien T, Silverberg JD, Nguyen TT: Nicotinic acid-induced toxicity associated with cytopenia and decreased levels of thyroxine-binding globulin. Mayo Clin Proc. 1992 May;67(5):465-8. doi: 10.1016/s0025-6196(12)60393-0. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine (PubMed:10454528, PubMed:10525100, PubMed:10966938, PubMed:17509700, PubMed:20722056, PubMed:33124720). Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 11.3 (PubMed:10454528, PubMed:10525100, PubMed:10966938). In intestinal epithelia, transports the quorum-sensing pentapeptide CSF (competence and sporulation factor) from Bacillus Subtilis wich induces cytoprotective heat shock proteins contributing to intestinal homeostasis (PubMed:18005709). May also contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable)
- Specific Function
- (r)-carnitine transmembrane transporter activity
- Gene Name
- SLC22A5
- Uniprot ID
- O76082
- Uniprot Name
- Organic cation/carnitine transporter 2
- Molecular Weight
- 62751.08 Da
References
- Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent transport of steroid sulfate conjugates and other specific organic anions (PubMed:10873595, PubMed:11159893, PubMed:11932330, PubMed:12724351, PubMed:14610227, PubMed:16908597, PubMed:18501590, PubMed:20507927, PubMed:22201122, PubMed:23531488, PubMed:25132355, PubMed:26383540, PubMed:27576593, PubMed:28408210, PubMed:29871943, PubMed:34628357). Responsible for the transport of estrone 3-sulfate (E1S) through the basal membrane of syncytiotrophoblast, highlighting a potential role in the placental absorption of fetal-derived sulfated steroids including the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S) (PubMed:11932330, PubMed:12409283). Also facilitates the uptake of sulfated steroids at the basal/sinusoidal membrane of hepatocytes, therefore accounting for the major part of organic anions clearance of liver (PubMed:11159893). Mediates the intestinal uptake of sulfated steroids (PubMed:12724351, PubMed:28408210). Mediates the uptake of the neurosteroids DHEA-S and pregnenolone sulfate (PregS) into the endothelial cells of the blood-brain barrier as the first step to enter the brain (PubMed:16908597, PubMed:25132355). Also plays a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May act as a heme transporter that promotes cellular iron availability via heme oxygenase/HMOX2 and independently of TFRC (PubMed:35714613). Also transports heme by-product coproporphyrin III (CPIII), and may be involved in their hepatic disposition (PubMed:26383540). Mediates the uptake of other substrates such as prostaglandins D2 (PGD2), E1 (PGE1) and E2 (PGE2), taurocholate, L-thyroxine, leukotriene C4 and thromboxane B2 (PubMed:10873595, PubMed:14610227, PubMed:19129463, PubMed:29871943, Ref.25). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:14610227, PubMed:19129463, PubMed:22201122). The exact transport mechanism has not been yet deciphered but most likely involves an anion exchange, coupling the cellular uptake of organic substrate with the efflux of an anionic compound (PubMed:19129463, PubMed:20507927, PubMed:26277985). Hydrogencarbonate/HCO3(-) acts as a probable counteranion that exchanges for organic anions (PubMed:19129463). Cytoplasmic glutamate may also act as counteranion in the placenta (PubMed:26277985). An inwardly directed proton gradient has also been proposed as the driving force of E1S uptake with a (H(+):E1S) stoichiometry of (1:1) (PubMed:20507927)
- Specific Function
- Bile acid transmembrane transporter activity
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76697.93 Da
References
- Kobayashi D, Nozawa T, Imai K, Nezu J, Tsuji A, Tamai I: Involvement of human organic anion transporting polypeptide OATP-B (SLC21A9) in pH-dependent transport across intestinal apical membrane. J Pharmacol Exp Ther. 2003 Aug;306(2):703-8. Epub 2003 Apr 30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Bidirectional proton-coupled monocarboxylate transporter (PubMed:12946269, PubMed:32946811, PubMed:33333023). Catalyzes the rapid transport across the plasma membrane of many monocarboxylates such as lactate, pyruvate, acetate and the ketone bodies acetoacetate and beta-hydroxybutyrate, and thus contributes to the maintenance of intracellular pH (PubMed:12946269, PubMed:33333023). The transport direction is determined by the proton motive force and the concentration gradient of the substrate monocarboxylate. MCT1 is a major lactate exporter (By similarity). Plays a role in cellular responses to a high-fat diet by modulating the cellular levels of lactate and pyruvate that contribute to the regulation of central metabolic pathways and insulin secretion, with concomitant effects on plasma insulin levels and blood glucose homeostasis (By similarity). Facilitates the protonated monocarboxylate form of succinate export, that its transient protonation upon muscle cell acidification in exercising muscle and ischemic heart (PubMed:32946811). Functions via alternate outward- and inward-open conformation states. Protonation and deprotonation of 309-Asp is essential for the conformational transition (PubMed:33333023)
- Specific Function
- Carboxylic acid transmembrane transporter activity
- Gene Name
- SLC16A1
- Uniprot ID
- P53985
- Uniprot Name
- Monocarboxylate transporter 1
- Molecular Weight
- 53943.685 Da
References
- Tamai I, Sai Y, Ono A, Kido Y, Yabuuchi H, Takanaga H, Satoh E, Ogihara T, Amano O, Izeki S, Tsuji A: Immunohistochemical and functional characterization of pH-dependent intestinal absorption of weak organic acids by the monocarboxylic acid transporter MCT1. J Pharm Pharmacol. 1999 Oct;51(10):1113-21. [Article]
- Tachikawa M, Murakami K, Martin PM, Hosoya K, Ganapathy V: Retinal transfer of nicotinate by H+ -monocarboxylate transporter at the inner blood-retinal barrier. Microvasc Res. 2011 Nov;82(3):385-90. doi: 10.1016/j.mvr.2011.06.009. Epub 2011 Jun 29. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Acts as an electrogenic sodium (Na(+)) and chloride (Cl-)-dependent sodium-coupled solute transporter, including transport of monocarboxylates (short-chain fatty acids including L-lactate, D-lactate, pyruvate, acetate, propionate, valerate and butyrate), mocarboxylate drugs (nicotinate, benzoate, salicylate and 5-aminosalicylate) and ketone bodies (beta-D-hydroxybutyrate, acetoacetate and alpha-ketoisocaproate), with a Na(+):substrate stoichiometry of between 4:1 and 2:1 (PubMed:14966140, PubMed:15090606, PubMed:16729224, PubMed:16805814, PubMed:17178845, PubMed:17245649, PubMed:17526579, PubMed:20211600, PubMed:30604288). Catalyzes passive carrier mediated diffusion of iodide (PubMed:12107270). Mediates iodide transport from the thyrocyte into the colloid lumen through the apical membrane (PubMed:12107270). May be responsible for the absorption of D-lactate and monocarboxylate drugs from the intestinal tract (PubMed:17245649). Acts as a tumor suppressor, suppressing colony formation in colon cancer, prostate cancer and glioma cell lines (PubMed:12829793, PubMed:15867356, PubMed:18037591). May play a critical role in the entry of L-lactate and ketone bodies into neurons by a process driven by an electrochemical Na(+) gradient and hence contribute to the maintenance of the energy status and function of neurons (PubMed:16805814). Mediates sodium-coupled electrogenic transport of pyroglutamate (5-oxo-L-proline) (PubMed:20211600). Can mediate the transport of chloride, bromide, iodide and nitrate ions when the external concentration of sodium ions is reduced (PubMed:19864324)
- Specific Function
- Lactate transmembrane transporter activity
- Gene Name
- SLC5A8
- Uniprot ID
- Q8N695
- Uniprot Name
- Sodium-coupled monocarboxylate transporter 1
- Molecular Weight
- 66577.005 Da
References
- Gopal E, Fei YJ, Miyauchi S, Zhuang L, Prasad PD, Ganapathy V: Sodium-coupled and electrogenic transport of B-complex vitamin nicotinic acid by slc5a8, a member of the Na/glucose co-transporter gene family. Biochem J. 2005 May 15;388(Pt 1):309-16. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Proton-dependent transporter of monocarboxylates such as L-lactate and pyruvate (PubMed:11101640, PubMed:23935841, PubMed:31719150). Plays a predominant role in L-lactate efflux from highly glycolytic cells (By similarity)
- Specific Function
- Lactate
- Gene Name
- SLC16A3
- Uniprot ID
- O15427
- Uniprot Name
- Monocarboxylate transporter 4
- Molecular Weight
- 49468.9 Da
References
- Shimada A, Nakagawa Y, Morishige H, Yamamoto A, Fujita T: Functional characteristics of H+ -dependent nicotinate transport in primary cultures of astrocytes from rat cerebral cortex. Neurosci Lett. 2006 Jan 16;392(3):207-12. Epub 2005 Oct 5. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 15, 2024 21:55