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Riboflavin
Identification
- Name
- Riboflavin
- Accession Number
- DB00140
- Description
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).
- Associated Conditions
- Associated Therapies
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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 Unlock Additional DataAcyclovir 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. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- 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 Unlock Additional DataB-2 Caps 100mg Capsule Oral Twin Laboratories Inc. 1995-12-31 1999-11-10 Canada 
B2 Tab 100mg Tablet Oral Vita Health Products Inc 1979-12-31 2002-07-31 Canada Riboflavin 5 Phosphate Cap 50mg Capsule Oral Thorne Research Inc. 1985-12-31 2001-07-13 Canada Riboflavin Tab 10mg Tablet Oral Swiss Herbal Remedies Ltd. 1971-12-31 1999-09-09 Canada Riboflavin Tab 5mg Tablet Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. 1957-12-31 2002-07-31 Canada Riboflavin-S Tab 25mg Tablet Oral Nutri West Products Ltd. 1993-12-31 1997-08-05 Canada Vit B2 Ctr Srt 200mg Tablet, extended release Oral Bioenergy Inc. 1979-12-31 1998-06-03 Canada Vita-flavine Cap 100mg Capsule Oral Les Laboratoires Vachon Inc. 1991-12-31 2001-08-07 Canada Vitamin B-2 Capsule Oral Sisu Inc. 2001-09-01 2006-07-31 Canada Vitamin B-2 50 Mg Tablets Tablet Oral General Nutrition Canada Inc. 1997-04-18 2006-08-03 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- 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 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) + Choline (2.222 mg) + Inositol (2.222 mg) + Nicotinamide (1.111 mg) + Pipradrol hydrochloride (.044 mg) + Pyridoxine hydrochloride (.042 mg) + Thiamine hydrochloride (.222 mg) Liquid Oral Merrell Pharms Inc., Division Of Merrell Dow (Can) 1967-12-31 1996-09-09 Canada Alertonic Riboflavin (0.111 mg) + Choline (2.222 mg) + Inositol (2.222 mg) + Nicotinamide (1.111 mg) + Pipradrol hydrochloride (0.044 mg) + Pyridoxine hydrochloride (0.042 mg) + Thiamine hydrochloride (0.222 mg) 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 Allbee C 800 Tab Riboflavin (17 mg) + Ascorbic acid (800 mg) + Cyanocobalamin (17 mcg) + D-alpha-Tocopherol acetate (45 unit) + Nicotinamide (100 mg) + Calcium pantothenate (33 mg) + Pyridoxine hydrochloride (30 mg) + Thiamine mononitrate (15 mg) Tablet Oral Whitehall Robins Inc. 1994-12-31 2003-08-01 Canada Allbee With C 550 Cap Riboflavin (10 mg) + Ascorbic acid (550 mg) + Nicotinamide (50 mg) + Calcium pantothenate (10 mg) + Pyridoxine hydrochloride (5 mg) + Thiamine mononitrate (15 mg) Capsule Oral Whitehall Robins Inc. 1994-12-31 2003-08-01 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
- Food and Beverages
- 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)
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[[email protected]](O)[[email protected]](O)[[email protected]](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. [PubMed:8604671]
- 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
- AHFS Codes
- 88:08.00 — Vitamin B Complex
- 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 / Pregnancy / Vomiting 1 4 Completed Treatment Pregnancy 1 4 Completed Treatment Progressive Keratoconus / Thin Corneas 1 4 Completed Treatment Smoking Addiction 1 4 Not Yet Recruiting Treatment Keratitis bacterial 1 4 Recruiting Treatment Hyperuricemia 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 Elixir Oral Capsule, liquid filled Oral 50 mg Tablet, coated 15 mg Syrup Oral 5 mg/5ml Solution 2.5 mg/ml Tablet, film coated Oral 25 mg Powder, for solution Intramuscular; Intravenous Tablet 250 mg Granule Oral Solution Oral 50 mg Tablet, coated Oral 20 mg Solution Intramuscular 50 mg Tablet, coated Oral 50 mg Solution Intramuscular 300 mg Capsule, liquid filled Oral Capsule Oral Tablet, film coated 8000 IU Capsule, coated Oral Tablet 4000 IU Capsule 4000 IU Tablet, effervescent Oral Tablet Oral 4000 IU Liquid Oral Tablet 15 mg Lozenge Oral Syrup Oral Capsule, delayed release Oral 0.6 mg Tablet, delayed release Oral Syrup Oral 1 g Tablet, coated Oral 150 mcg Tablet, coated Oral Tablet, coated Oral 15 mg Injection Intramuscular Tablet Oral 8.3 mg Solution Intravenous Liquid; tablet Oral Tablet, chewable Oral Liquid Intravenous Granule, effervescent Oral Solution Oral Syrup Oral 2500 IU/5ml Capsule, liquid filled Oral 0.25 mg Tablet Oral Capsule, liquid filled Oral 0.6 mg Tablet Oral 2.5 mg Tablet, orally disintegrating Oral Capsule, delayed release Oral 150 mg Solution Oral 100 mg Tablet, film coated Oral 15 mg Syrup Oral 1500 IU Suspension / drops Oral Solution / drops Oral Tablet, film coated Oral Capsule, liquid filled Oral 0.1 mg Pill Oral Capsule, gelatin coated Oral Tablet Oral Tablet Syrup 1250 IU Syrup 150 ml Solution 2.5 mg Capsule, liquid filled Oral 1 mg Capsule, extended release Oral Tablet, extended release Oral Powder, for solution 3500 IU Capsule; liquid Oral Tablet 50 mg Injection, powder, lyophilized, for solution Intramuscular; Intravenous 3500 IU Solution Intravenous 5 g Capsule Oral 3.5 mg Tablet, chewable Oral 5000 IU Capsule, liquid filled Oral 25 mg Capsule, liquid filled Oral 200 mg Tablet, extended release Oral Capsule Oral Tablet Oral 15 mg Syrup Oral 1250 IU/5mL Syrup Oral 320 mg Kit Oral Powder Oral Tablet Oral 200 mg Tablet, film coated Oral 200 mg Granule Oral 70 mcg - 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)
- Download (11.3 KB)
- Spectra
Targets
- 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. [PubMed:16081269]
- 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. [PubMed:15668000]
- 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. [PubMed:17290783]
- 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. [PubMed:16183635]
- 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. [PubMed:16962092]
- 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. [PubMed:21308351]
- 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. [PubMed:20143812]
- 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. [PubMed:20148904]
- 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. [PubMed:14769034]
- 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. [PubMed:16544142]
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. [PubMed:17868200]
- 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. [PubMed:3676170]
- 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. [PubMed:15454103]
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. [PubMed:9880528]
Drug created on June 13, 2005 07:24 / Updated on September 22, 2020 02:11
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