Riboflavin
Identification
- Summary
Riboflavin is a vitamin used to correct vitamin B2 deficiency.
- Brand Names
- Alertonic, Concept Ob, Irospan 24/6 Kit, Mvc-fluoride, Natafort, Pregvit, Tandem Plus, Vitafol-one
- Generic Name
- Riboflavin
- DrugBank Accession Number
- DB00140
- Background
Nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, and leafy vegetables. The richest natural source is yeast. It occurs in the free form only in the retina of the eye, in whey, and in urine; its principal forms in tissues and cells are as flavin mononucleotide and flavin-adenine dinucleotide.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Nutraceutical, Vet approved
- Structure
Structure for Riboflavin (DB00140)
- Weight
- Average: 376.3639
Monoisotopic: 376.138284392 - Chemical Formula
- C17H20N4O6
- Synonyms
- 1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitol
- 6,7-Dimethyl-9-D-ribitylisoalloxazine
- 7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine
- 7,8-Dimethyl-10-ribitylisoalloxazine
- Lactoflavin
- Lactoflavine
- Riboflavin
- Riboflavina
- Riboflavine
- Riboflavinum
- Vitamin B2
- Vitamin Bi
- Vitamin G
- External IDs
- E101
- INS NO. 101(I)
- NCI-0033298
- NSC-33298
Pharmacology
- Indication
For the treatment of ariboflavinosis (vitamin B2 deficiency).
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- Associated Therapies
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Riboflavin or vitamin B2 is an easily absorbed, water-soluble micronutrient with a key role in maintaining human health. Like the other B vitamins, it supports energy production by aiding in the metabolising of fats, carbohydrates, and proteins. Vitamin B2 is also required for red blood cell formation and respiration, antibody production, and for regulating human growth and reproduction. It is essential for healthy skin, nails, hair growth and general good health, including regulating thyroid activity. Riboflavin also helps in the prevention or treatment of many types of eye disorders, including some cases of cataracts.
- Mechanism of action
Binds to riboflavin hydrogenase, riboflavin kinase, and riboflavin synthase. Riboflavin is the precursor of flavin mononucleotide (FMN, riboflavin monophosphate) and flavin adenine dinucleotide (FAD). The antioxidant activity of riboflavin is principally derived from its role as a precursor of FAD and the role of this cofactor in the production of the antioxidant reduced glutathione. Reduced glutathione is the cofactor of the selenium-containing glutathione peroxidases among other things. The glutathione peroxidases are major antioxidant enzymes. Reduced glutathione is generated by the FAD-containing enzyme glutathione reductase.
Target Actions Organism ARiboflavin kinase ligandHumans ARiboflavin synthase otherEscherichia coli (strain K12) AFlavin reductase (NADPH) product ofHumans - Absorption
Vitamin B2 is readily absorbed from the upper gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
60%
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
66-84 minutes
- Clearance
Not Available
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
Not Available
- Pathways
Pathway Category Riboflavin 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 softwareAcyclovir The excretion of Acyclovir can be decreased when combined with Riboflavin. Adefovir dipivoxil The excretion of Adefovir dipivoxil can be decreased when combined with Riboflavin. Alprostadil The excretion of Alprostadil can be decreased when combined with Riboflavin. Aminohippuric acid The excretion of Aminohippuric acid can be decreased when combined with Riboflavin. Captopril The excretion of Captopril can be decreased when combined with Riboflavin. Cefazolin The excretion of Cefazolin can be decreased when combined with Riboflavin. Cefdinir The excretion of Cefdinir can be decreased when combined with Riboflavin. Cefotiam The excretion of Cefotiam can be decreased when combined with Riboflavin. Ceftibuten The excretion of Ceftibuten can be decreased when combined with Riboflavin. Ceftizoxime The excretion of Ceftizoxime can be decreased when combined with Riboflavin. 
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- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Riboflavin sodium 04SRR95RP8 7681-29-0 YXJHJCDOUFKMBG-BMZHGHOISA-M - Product Images
- International/Other Brands
- Bisulase
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image B-2 Caps 100mg Capsule 100 mg / cap Oral Twin Laboratories Inc. 1995-12-31 1999-11-10 Canada 
B2 Tab 100mg Tablet 100 mg Oral Vita Health Products Inc 1979-12-31 2002-07-31 Canada PHARMANIAGA RIBOFLAVIN TABLET 3MG Tablet Oral PHARMANIAGA MANUFACTURING BERHAD 2020-09-08 Not applicable Malaysia 
Riboflavin 5 Phosphate Cap 50mg Capsule 50 mg / cap Oral Thorne Research Inc. 1985-12-31 2001-07-13 Canada Riboflavin Tab 10mg Tablet 10 mg / tab Oral Swiss Herbal Remedies Ltd. 1971-12-31 1999-09-09 Canada Riboflavin Tab 5mg Tablet 5 mg Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1957-12-31 2002-07-31 Canada RIBOFLAVIN TABLETS 10 MG. Tablet 10 mg Oral บริษัท อินแพคฟาร์มา จำกัด 1995-02-24 2020-09-29 Thailand 
Riboflavin-S Tab 25mg Tablet 25 mg / tab Oral Nutri West Products Ltd. 1993-12-31 1997-08-05 Canada RIBOFLAVINE TABLET 5MG Tablet Oral ROYCE PHARMA MANUFACTURING SDN. BHD. 2020-09-08 2020-12-18 Malaysia Vit B2 Ctr Srt 200mg Tablet, extended release 200 mg / tab Oral Bioenergy Inc. 1979-12-31 1998-06-03 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 24 Multivitamins + Minerals Riboflavin (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 (2 mg) + Molybdenum (20 mcg) + Niacin (25 mg) + Calcium pantothenate (25 mg) + Potassium (15 mg) + Potassium Iodide (.1 mg) + Pyridoxine hydrochloride (25 mg) + Racemethionine (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 50 Plus Riboflavin (20 mg) + Ascorbic acid (200 mg) + Biotin (20 mcg) + Choline bitartrate (20 mg) + Cyanocobalamin (20 mcg) + Folic acid (.2 mg) + Inositol (20 mg) + Niacin (20 mg) + Calcium pantothenate (20 mg) + Pyridoxine hydrochloride (20 mg) + Racemethionine (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 50 Plus Multiple Vitamins & Minerals Riboflavin (3.2 mg) + Ascorbic acid (90 mg) + Biotin (45 mcg) + Calcium (200 mg) + Cholecalciferol (400 unit) + Chromium (10 mcg) + Copper (2 mg) + Cyanocobalamin (25 mcg) + Folic acid (0.4 mg) + Magnesium (100 mg) + Manganese (5 mg) + Molybdenum (25 mcg) + Nicotinamide (40 mg) + Pantothenic acid (10 mg) + Potassium Iodide (0.15 mg) + Pyridoxine hydrochloride (3 mg) + Selenium (25 mcg) + Thiamine mononitrate (2.25 mg) + Vanadium (10 mcg) + Vitamin A palmitate (6000 unit) + Zinc (15 mg) Tablet Oral Gfr Pharma Ltd. 2002-10-20 2004-06-15 Canada Adeks - Dps Riboflavin (0.6 mg / mL) + Ascorbic acid (45 mg / mL) + Beta carotene (1 mg / mL) + Biotin (15 mcg / mL) + Cyanocobalamin (4 mcg / mL) + Nicotinamide (6 mg / mL) + Panthenol (3 mg / mL) + Phylloquinone (0.1 mg / mL) + Pyridoxine hydrochloride (0.6 mg / mL) + Thiamine (0.5 mg / mL) + Vitamin A palmitate (1500 unit / mL) + Vitamin D (400 unit / mL) + Vitamin E (40 unit / mL) + Zinc (5 mg / mL) Solution / drops Oral Axcan Pharma 1995-12-31 2007-10-01 Canada Adeks Tablets Riboflavin (1.3 mg) + Ascorbic acid (60 mg) + Beta carotene (3 mg) + Biotin (50 mcg) + Cholecalciferol (400 unit) + Cyanocobalamin (12 mcg) + Folic acid (0.2 mg) + Niacin (10 mg) + Calcium pantothenate (10 mg) + Phylloquinone (0.15 mg) + Pyridoxine (1.5 mg) + Thiamine (1.2 mg) + Vitamin A palmitate (4000 unit) + Vitamin E (150 unit) + Zinc (7.5 mg) Tablet Oral Axcan Pharma 1998-01-20 2011-04-20 Canada Adult Formula 50+ Riboflavin (3.4 mg) + Ascorbic acid (120 mg) + Beta carotene (3000 unit) + Biotin (30 mcg) + Calcium (220 mg) + Cholecalciferol (400 unit) + Chromium (10 mcg) + Copper (2 mg) + Cyanocobalamin (25 mcg) + Folic acid (0.4 mg) + Iodine (0.15 mg) + Magnesium (100 mg) + Manganese (2.5 mg) + Molybdenum (10 mcg) + Nicotinamide (20 mg) + Calcium pantothenate (20 mg) + Potassium (37.5 mg) + Pyridoxine hydrochloride (6 mg) + Selenium (10 mcg) + Thiamine hydrochloride (4.5 mg) + Vitamin A palmitate (3000 unit) + Zinc (15 mg) + alpha-Tocopherol acetate (60 unit) Tablet Oral Wn Pharmaceuticals Ltd. 2002-04-25 2009-09-28 Canada Advanced B & T Formula Riboflavin (2.67 mg) + Ascorbic acid (33.3 mg) + Calcium (200 mg) + Chromium (33.33 mcg) + Copper (0.5 mg) + Cyanocobalamin (6.67 mcg) + Folic acid (0.133 mg) + Iron (1.67 mg) + Magnesium (83.3 mg) + Manganese (3.33 mg) + Nicotinamide (6.67 mg) + Calcium pantothenate (5 mg) + Phosphorus (100 mg) + Potassium (16.67 mg) + Pyridoxine hydrochloride (6.67 mg) + Selenium (33.33 mcg) + Silicon (0.333 mg) + Sodium molybdate (16.67 mcg) + Thiamine (2.67 mg) + Vanadium (8.33 mg) + Vitamin D (66.67 unit) + Zinc (5 mg) Capsule Oral Nutraceutical Corporation Not applicable Not applicable Canada Alertonic Riboflavin (.111 mg / mL) + Choline (2.222 mg / mL) + Inositol (2.222 mg / mL) + Nicotinamide (1.111 mg / mL) + Pipradrol hydrochloride (.044 mg / mL) + Pyridoxine hydrochloride (.042 mg / mL) + Thiamine hydrochloride (.222 mg / mL) Liquid Oral Merrell Pharms Inc., Division Of Merrell Dow (Can) 1967-12-31 1996-09-09 Canada Alertonic Riboflavin (0.111 mg / mL) + Choline (2.222 mg / mL) + Inositol (2.222 mg / mL) + Nicotinamide (1.111 mg / mL) + Pipradrol hydrochloride (0.044 mg / mL) + Pyridoxine hydrochloride (0.042 mg / mL) + Thiamine hydrochloride (0.222 mg / mL) Elixir Oral Odan Laboratories Ltd 1995-12-31 Not applicable Canada Alkadrenergy Tablets Riboflavin (6.25 mg) + Ascorbic acid (60 mg) + Beta carotene (2500 unit) + Biotin (150 mcg) + Calcium (50 mg) + Choline (100 mg) + Chromic chloride (5 mcg) + Cyanocobalamin (45 mcg) + Folic acid (0.2 mg) + Inositol (25 mg) + Iodine (0.1 mg) + Magnesium (50 mg) + Manganese (0.5 mg) + Molybdenum (3 mcg) + Nicotinamide (40 mg) + Pantothenic acid (15 mg) + Pyridoxine hydrochloride (6.25 mg) + Sodium selenite (37.5 mcg) + Thiamine (6.25 mg) + Zinc (9 mg) + alpha-Tocopherol acetate (15 unit) Tablet Oral Morter Healthsystem Not applicable Not applicable Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Active FE Riboflavin (4 mg/1) + Ascorbic acid (160 mg/1) + Beta carotene (2100 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (30 ug/1) + DL-alpha tocopheryl acetate (40 [iU]/1) + Folic acid (1250 ug/1) + Iron (75 mg/1) + Magnesium oxide (30 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Thiamine hydrochloride (4 mg/1) + Zinc oxide (20 mg/1) Tablet Oral Gm Pharmaceuticals 2013-11-11 Not applicable US 
Active OB Riboflavin (4 mg/1) + Ascorbic acid (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (2 mg/1) + Cyanocobalamin (30 ug/1) + D-alpha-Tocopherol acetate (30 [iU]/1) + Doconexent (320 mg/1) + Folic acid (1 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc oxide (30 mg/1) Capsule, liquid filled Oral Gm Pharmaceuticals 2013-10-28 2017-03-31 US B-Combo Riboflavin (1 mg/1mL) + Dexpanthenol (1 mg/1mL) + Mecobalamin (1 mg/1mL) + Nicotinamide (1 mg/1mL) + Pyridoxine (1 mg/1mL) + Thiamine chloride (1 mg/1mL) Injection Intramuscular Perdido Key Health And Wellness Inc 2015-11-23 Not applicable US Bacmin Riboflavin (20 mg/1) + Ascorbic acid (500 mg/1) + Biotin (150 ug/1) + Chromium Cr-51 chloride (0.1 mg/1) + Cupric oxide (3 mg/1) + Cyanocobalamin (50 ug/1) + Ferrous fumarate (27 mg/1) + Flavone (50 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (50 mg/1) + Manganese gluconate (5 mg/1) + Nicotinamide (100 mg/1) + Calcium pantothenate (25 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Selenomethionine (50 ug/1) + Thiamine mononitrate (20 mg/1) + Vitamin A acetate (2000 [iU]/1) + Zinc oxide (22.5 mg/1) + alpha-Tocopherol acetate (30 [iU]/1) Tablet, coated Oral Marnel Pharmaceuticals, Llc 2000-04-01 Not applicable US Bal-Care DHA Riboflavin (4 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cholecalciferol (840 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (.012 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (430 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1) Kit Oral Pru Gen Pharmaceuticals 2012-05-01 Not applicable US Bal-Care DHA Essential Riboflavin (4 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2850 [iU]/1) + Calcium carbonate (219 mg/1) + Cholecalciferol (840 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (.012 mg/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (.223 mg/1) + Iron sucrose (1.35 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (374 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Sodium feredetate (25.65 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1) Kit Oral Pru Gen Pharmaceuticals 2012-05-01 Not applicable US Biovita Riboflavin (0.2 mg/1g) + Ascorbic acid (5 mg/1g) + Bacillus subtilis (3 mg/1g) + Calcium phosphate dihydrate (20 mg/1g) + Nicotinamide (0.1 mg/1g) + Thiamine mononitrate (0.3 mg/1g) Granule Oral Ildong Pharmaceutical Co., Ltd. 2015-06-03 2019-09-13 US Biovita Riboflavin (0.2 mg/1g) + Ascorbic acid (5 mg/1g) + Bacillus subtilis (3 mg/1g) + Calcium phosphate dihydrate (20 mg/1g) + Nicotinamide (0.1 mg/1g) + Thiamine mononitrate (0.3 mg/1g) Granule Oral OASIS TRADING 2018-12-25 Not applicable US C-Nate DHA Riboflavin (3 mg/1) + Ascorbic acid (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (1 mg/1) + Cyanocobalamin (15 ug/1) + Ferrous fumarate (28 mg/1) + Folic acid (1 mg/1) + Magnesium (30 mg/1) + Omega-3 fatty acids (200 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Thiamine mononitrate (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc oxide (20 mg/1) Capsule, gelatin coated Oral Centurion Labs, LLC 2013-01-01 Not applicable US Cavan Alpha Riboflavin (4 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (3000 [iU]/1) + Calcium carbonate (230 mg/1) + Cholecalciferol (800 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (3 mg/1) + Folic acid (1 mg/1) + Iodine (220 ug/1) + Iron (27 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (300 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1) Kit Oral Seton Pharmaceuticals 2010-07-01 2013-09-30 US
Categories
- ATC Codes
- A11HA04 — Riboflavin (vit b2)
- A11HA — Other plain vitamin preparations
- A11H — OTHER PLAIN VITAMIN PREPARATIONS
- A11 — VITAMINS
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- Alimentary Tract and Metabolism
- Biological Factors
- Coenzymes
- Dermatologicals
- Diet, Food, and Nutrition
- Enzymes and Coenzymes
- Flavins
- Food
- Growth Substances
- Heterocyclic Compounds, Fused-Ring
- Micronutrients
- OAT1/SLC22A6 inhibitors
- Ophthalmologicals
- Photosensitizing Agents
- Physiological Phenomena
- Pigments, Biological
- Pteridines
- Radiation-Sensitizing Agents
- Sensory Organs
- Vitamin B Complex
- Vitamins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, with a structure characterized by an isoalloaxzine tricyclic ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pteridines and derivatives
- Sub Class
- Alloxazines and isoalloxazines
- Direct Parent
- Flavins
- Alternative Parents
- Quinoxalines / Pyrimidones / Pyrazines / Benzenoids / Vinylogous amides / Heteroaromatic compounds / Secondary alcohols / Lactams / Polyols / Azacyclic compounds show 5 more
- Substituents
- Alcohol / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Diazanaphthalene / Flavin / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Organic nitrogen compound show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- flavin (CHEBI:17015) / Water-soluble vitamins (C00255)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- TLM2976OFR
- CAS number
- 83-88-5
- InChI Key
- AUNGANRZJHBGPY-SCRDCRAPSA-N
- InChI
- InChI=1S/C17H20N4O6/c1-7-3-9-10(4-8(7)2)21(5-11(23)14(25)12(24)6-22)15-13(18-9)16(26)20-17(27)19-15/h3-4,11-12,14,22-25H,5-6H2,1-2H3,(H,20,26,27)/t11-,12+,14-/m0/s1
- IUPAC Name
- 7,8-dimethyl-10-[(2S,3S,4R)-2,3,4,5-tetrahydroxypentyl]-2H,3H,4H,10H-benzo[g]pteridine-2,4-dione
- SMILES
- CC1=C(C)C=C2N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=NC2=C1
References
- Synthesis Reference
Hansgeorg Ernst, Wolfram Schmidt, Joachim Paust, "Preparation of riboflavin." U.S. Patent US4567261, issued August, 1958.
US4567261- General References
- Zempleni J, Galloway JR, McCormick DB: Pharmacokinetics of orally and intravenously administered riboflavin in healthy humans. Am J Clin Nutr. 1996 Jan;63(1):54-66. [Article]
- External Links
- Human Metabolome Database
- HMDB0000244
- KEGG Drug
- D00050
- KEGG Compound
- C00255
- PubChem Compound
- 493570
- PubChem Substance
- 46507342
- ChemSpider
- 431981
- BindingDB
- 50362895
- 9346
- ChEBI
- 17015
- ChEMBL
- CHEMBL1534
- ZINC
- ZINC000002036848
- PharmGKB
- PA451242
- PDBe Ligand
- RBF
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Riboflavin
- PDB Entries
- 1bu5 / 1hze / 1i18 / 1kyv / 1l5r / 1mog / 1nb9 / 1pkv / 1t6z / 2a58 … show 30 more
- MSDS
- Download (39.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Health Services Research Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Lactic Acidosis / Lipodystrophies 1 4 Completed Treatment Diabetic Macular Edema (DME) 1 4 Completed Treatment Diabetic Peripheral Neuropathic Pain (DPN) 1 4 Completed Treatment Fatigue 1 4 Completed Treatment Hyperemesis Gravidarum / Morning Sickness / Nausea / Pregnant State / Vomiting 1 4 Completed Treatment Pain 1 4 Completed Treatment Pregnant State 1 4 Completed Treatment Progressive Keratoconus / Thin Corneas 1 4 Completed Treatment Smoking Addiction 1 4 Recruiting Treatment Progressive Keratoconus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amend
- C.O. Truxton Inc.
- Carlisle Laboratories Inc.
- Freeda Vitamins
- Gonberetica
- Key Co.
- Magno-Humphries Laboratories
- Martica Enterprises Inc.
- Martin Surgical Supply
- Mason Distributors
- Merit Pharmaceuticals
- Nexgen Pharma Inc.
- Pamlab LLC
- Particle Dynamics Co.
- Pharmetics Inc.
- Red River Pharma Manufacturing
- Sciele Pharma Inc.
- Dosage Forms
Form Route Strength Capsule Tablet, delayed release Oral Solution Injection, solution Intramuscular; Intravenous Granule Oral Elixir Oral Solution Intramuscular Solution Parenteral Tablet, coated Oral 20 mg Tablet, coated Oral 50 mg Capsule, liquid filled Oral Capsule Oral Tablet, film coated Capsule, coated Oral Tablet Tablet, effervescent Oral Liquid Oral Powder, for solution Intravenous Lozenge Oral Gel Oral Capsule, delayed release Oral Tablet, extended release Oral Tablet, coated Oral 150 mcg Tablet, coated Oral Injection Intramuscular Liquid; tablet Oral Tablet, chewable Oral Liquid Intravenous Granule, effervescent Oral Solution Oral Tablet, sugar coated Oral Tablet Oral Powder, for solution Oral Tablet, orally disintegrating Oral Suspension / drops Oral Solution / drops Oral Tablet, film coated Oral Pill Oral Capsule, gelatin coated Oral Capsule Oral 50 mg / cap Tablet Oral 10 mg / tab Tablet Oral 5 mg Tablet Oral 25 mg / tab Tablet Oral Syrup Injection, powder, lyophilized, for solution Intravenous Solution Intravenous Capsule, extended release Oral Powder, for solution Intramuscular; Intravenous Capsule; liquid Oral Injection Intravenous Syrup Oral Injection, powder, lyophilized, for solution Intramuscular; Intravenous Tablet, extended release Oral 200 mg / tab Capsule Oral 100 mg / cap Capsule Oral 100 mg Tablet Oral 100 mg / tab Tablet Oral 4 mg / tab Kit Oral Powder Oral Solution 7 mg/1ml Solution 5 mg/1ml Tablet Oral 10 mg Tablet Oral 100 mg Tablet Oral 50 mg Tablet Oral 25 mg - Prices
Unit description Cost Unit Riboflavin powder 0.44USD g Riboflavin 100 mg tablet 0.09USD tablet Riboflavin 50 mg tablet 0.08USD tablet Vitamin b-2 50 mg tablet 0.08USD tablet Ribo 100 mg tablet 0.04USD tablet Vitamin b-2 25 mg tablet 0.02USD tablet 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) 280 dec °C PhysProp water solubility 84.7 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP -1.46 HANSCH,C ET AL. (1995) logS -3.68 ADME Research, USCD pKa 10.2 BUDAVARI,S ET AL. (1996) - Predicted Properties
Property Value Source Water Solubility 0.657 mg/mL ALOGPS logP -1 ALOGPS logP -0.92 ChemAxon logS -2.8 ALOGPS pKa (Strongest Acidic) 6.97 ChemAxon pKa (Strongest Basic) 0.76 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 155.05 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 96.27 m3·mol-1 ChemAxon Polarizability 37.5 Å3 ChemAxon Number of Rings 3 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 + 0.9156 Blood Brain Barrier - 0.8495 Caco-2 permeable - 0.7122 P-glycoprotein substrate Substrate 0.7414 P-glycoprotein inhibitor I Non-inhibitor 0.8708 P-glycoprotein inhibitor II Non-inhibitor 0.9466 Renal organic cation transporter Non-inhibitor 0.9279 CYP450 2C9 substrate Non-substrate 0.7819 CYP450 2D6 substrate Non-substrate 0.8435 CYP450 3A4 substrate Non-substrate 0.522 CYP450 1A2 substrate Inhibitor 0.8531 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9516 CYP450 2C19 inhibitor Inhibitor 0.7302 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9203 Ames test Non AMES toxic 0.804 Carcinogenicity Non-carcinogens 0.7954 Biodegradation Not ready biodegradable 0.9641 Rat acute toxicity 1.6067 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9395 hERG inhibition (predictor II) Non-inhibitor 0.5362
Spectra
- Mass Spec (NIST)
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- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- General Function
- Riboflavin kinase activity
- Specific Function
- Catalyzes the phosphorylation of riboflavin (vitamin B2) to form flavin-mononucleotide (FMN), hence rate-limiting enzyme in the synthesis of FAD. Essential for TNF-induced reactive oxygen species (...
- Gene Name
- RFK
- Uniprot ID
- Q969G6
- Uniprot Name
- Riboflavin kinase
- Molecular Weight
- 17623.08 Da
References
- Werner R, Manthey KC, Griffin JB, Zempleni J: HepG2 cells develop signs of riboflavin deficiency within 4 days of culture in riboflavin-deficient medium. J Nutr Biochem. 2005 Oct;16(10):617-24. [Article]
- Solovieva IM, Kreneva RA, Errais Lopes L, Perumov DA: The riboflavin kinase encoding gene ribR of Bacillus subtilis is a part of a 10 kb operon, which is negatively regulated by the yrzC gene product. FEMS Microbiol Lett. 2005 Feb 1;243(1):51-8. [Article]
- Ishchuk OP, Iatsyshyn VIu, Dmytruk KV, Voronovs'kyi AIa, Fedorovych DV, Sybirnyi AA: [Construction of the flavinogenic yeast Candida famata strains with high riboflavin kinase activity using gene engineering]. Ukr Biokhim Zh (1999). 2006 Sep-Oct;78(5):63-9. [Article]
- Sandoval FJ, Roje S: An FMN hydrolase is fused to a riboflavin kinase homolog in plants. J Biol Chem. 2005 Nov 18;280(46):38337-45. Epub 2005 Sep 23. [Article]
- Bertollo CM, Oliveira AC, Rocha LT, Costa KA, Nascimento EB Jr, Coelho MM: Characterization of the antinociceptive and anti-inflammatory activities of riboflavin in different experimental models. Eur J Pharmacol. 2006 Oct 10;547(1-3):184-91. Epub 2006 Jul 26. [Article]
- Hirano G, Izumi H, Yasuniwa Y, Shimajiri S, Ke-Yong W, Sasagiri Y, Kusaba H, Matsumoto K, Hasegawa T, Akimoto M, Akashi K, Kohno K: Involvement of riboflavin kinase expression in cellular sensitivity against cisplatin. Int J Oncol. 2011 Apr;38(4):893-902. doi: 10.3892/ijo.2011.938. Epub 2011 Feb 9. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Other
- General Function
- Riboflavin synthase activity
- Specific Function
- Catalyzes the dismutation of two molecules of 6,7-dimethyl-8-ribityllumazine, resulting in the formation of riboflavin and 5-amino-6-(D-ribitylamino)uracil.
- Gene Name
- ribC
- Uniprot ID
- P0AFU8
- Uniprot Name
- Riboflavin synthase
- Molecular Weight
- 23444.77 Da
References
- Kim RR, Illarionov B, Joshi M, Cushman M, Lee CY, Eisenreich W, Fischer M, Bacher A: Mechanistic insights on riboflavin synthase inspired by selective binding of the 6,7-dimethyl-8-ribityllumazine exomethylene anion. J Am Chem Soc. 2010 Mar 10;132(9):2983-90. doi: 10.1021/ja908395r. [Article]
- Long Q, Ji L, Wang H, Xie J: Riboflavin biosynthetic and regulatory factors as potential novel anti-infective drug targets. Chem Biol Drug Des. 2010 Apr;75(4):339-47. doi: 10.1111/j.1747-0285.2010.00946.x. Epub 2010 Feb 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Product of
- General Function
- Riboflavin reductase (nadph) activity
- Specific Function
- Broad specificity oxidoreductase that catalyzes the NADPH-dependent reduction of a variety of flavins, such as riboflavin, FAD or FMN, biliverdins, methemoglobin and PQQ (pyrroloquinoline quinone)....
- Gene Name
- BLVRB
- Uniprot ID
- P30043
- Uniprot Name
- Flavin reductase (NADPH)
- Molecular Weight
- 22119.215 Da
References
- Russell TR, Demeler B, Tu SC: Kinetic mechanism and quaternary structure of Aminobacter aminovorans NADH:flavin oxidoreductase: an unusual flavin reductase with bound flavin. Biochemistry. 2004 Feb 17;43(6):1580-90. [Article]
- van Pee KH, Patallo EP: Flavin-dependent halogenases involved in secondary metabolism in bacteria. Appl Microbiol Biotechnol. 2006 May;70(6):631-41. Epub 2006 Mar 17. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Cofactor
- General Function
- Serotonin binding
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Strolin Benedetti M, Tipton KF, Whomsley R: Amine oxidases and monooxygenases in the in vivo metabolism of xenobiotic amines in humans: has the involvement of amine oxidases been neglected? Fundam Clin Pharmacol. 2007 Oct;21(5):467-80. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Cofactor
- General Function
- Protein complex binding
- Specific Function
- Catalyzes the conversion of 5,10-methylenetetrahydrofolate to 5-methyltetrahydrofolate, a co-substrate for homocysteine remethylation to methionine.
- Gene Name
- MTHFR
- Uniprot ID
- P42898
- Uniprot Name
- Methylenetetrahydrofolate reductase
- Molecular Weight
- 74595.895 Da
References
- Bates CJ, Fuller NJ: The effect of riboflavin deficiency on methylenetetrahydrofolate reductase (NADPH) (EC 1.5.1.20) and folate metabolism in the rat. Br J Nutr. 1986 Mar;55(2):455-64. [Article]
- Macdonald HM, McGuigan FE, Fraser WD, New SA, Ralston SH, Reid DM: Methylenetetrahydrofolate reductase polymorphism interacts with riboflavin intake to influence bone mineral density. Bone. 2004 Oct;35(4):957-64. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Kuze K, Graves P, Leahy A, Wilson P, Stuhlmann H, You G: Heterologous expression and functional characterization of a mouse renal organic anion transporter in mammalian cells. J Biol Chem. 1999 Jan 15;274(3):1519-24. [Article]
Drug created on June 13, 2005 13:24 / Updated on August 05, 2021 19:41