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
Thumb
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.
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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.

TargetActionsOrganism
ARiboflavin kinase
ligand
Humans
ARiboflavin synthase
other
Escherichia coli (strain K12)
AFlavin reductase (NADPH)
product of
Humans
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
PathwayCategory
Riboflavin MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcyclovirThe excretion of Acyclovir can be decreased when combined with Riboflavin.
Adefovir dipivoxilThe excretion of Adefovir dipivoxil can be decreased when combined with Riboflavin.
AlprostadilThe excretion of Alprostadil can be decreased when combined with Riboflavin.
Aminohippuric acidThe excretion of Aminohippuric acid can be decreased when combined with Riboflavin.
CaptoprilThe excretion of Captopril can be decreased when combined with Riboflavin.
CefazolinThe excretion of Cefazolin can be decreased when combined with Riboflavin.
CefdinirThe excretion of Cefdinir can be decreased when combined with Riboflavin.
CefotiamThe excretion of Cefotiam can be decreased when combined with Riboflavin.
CeftibutenThe excretion of Ceftibuten can be decreased when combined with Riboflavin.
CeftizoximeThe excretion of Ceftizoxime can be decreased when combined with Riboflavin.
Additional Data Available
  • Extended Description
    Extended Description
    Available for Purchase

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity
    Available for Purchase

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level
    Available for Purchase

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action
    Available for Purchase

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Purchasing individual compounds or compound libraries for your research?
Learn More
Product Ingredients
IngredientUNIICASInChI Key
Riboflavin sodium04SRR95RP87681-29-0YXJHJCDOUFKMBG-BMZHGHOISA-M
Product Images
International/Other Brands
Bisulase
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
B-2 Caps 100mgCapsuleOralTwin Laboratories Inc.1995-12-311999-11-10Canada flag
B2 Tab 100mgTabletOralVita Health Products Inc1979-12-312002-07-31Canada flag
Riboflavin 5 Phosphate Cap 50mgCapsuleOralThorne Research Inc.1985-12-312001-07-13Canada flag
Riboflavin Tab 10mgTabletOralSwiss Herbal Remedies Ltd.1971-12-311999-09-09Canada flag
Riboflavin Tab 5mgTabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada flag
Riboflavin-S Tab 25mgTabletOralNutri West Products Ltd.1993-12-311997-08-05Canada flag
Vit B2 Ctr Srt 200mgTablet, extended releaseOralBioenergy Inc.1979-12-311998-06-03Canada flag
Vita-flavine Cap 100mgCapsuleOralLes Laboratoires Vachon Inc.1991-12-312001-08-07Canada flag
Vitamin B-2CapsuleOralSisu Inc.2001-09-012006-07-31Canada flag
Vitamin B-2 50 Mg TabletsTabletOralGeneral Nutrition Canada Inc.1997-04-182006-08-03Canada flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
24 Multivitamins + MineralsRiboflavin (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)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1997-04-302002-07-31Canada flag
50 PlusRiboflavin (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)TabletOralQuest Vitamins A Div Of Purity Life Health Products1998-08-042001-07-06Canada flag
50 Plus Multiple Vitamins & MineralsRiboflavin (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)TabletOralGfr Pharma Ltd.2002-10-202004-06-15Canada flag
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)TabletOralWn Pharmaceuticals Ltd.2002-04-252009-09-28Canada flag
Advanced B & T FormulaRiboflavin (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)CapsuleOralNutraceutical CorporationNot applicableNot applicableCanada flag
AlertonicRiboflavin (.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)LiquidOralMerrell Pharms Inc., Division Of Merrell Dow (Can)1967-12-311996-09-09Canada flag
AlertonicRiboflavin (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)ElixirOralOdan Laboratories Ltd1995-12-31Not applicableCanada flag
Alkadrenergy TabletsRiboflavin (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)TabletOralMorter HealthsystemNot applicableNot applicableCanada flag
Allbee C 800 TabRiboflavin (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)TabletOralWhitehall Robins Inc.1994-12-312003-08-01Canada flag
Allbee With C 550 CapRiboflavin (10 mg) + Ascorbic acid (550 mg) + Nicotinamide (50 mg) + Calcium pantothenate (10 mg) + Pyridoxine hydrochloride (5 mg) + Thiamine mononitrate (15 mg)CapsuleOralWhitehall Robins Inc.1994-12-312003-08-01Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Active FERiboflavin (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)TabletOralGm Pharmaceuticals2013-11-11Not applicableUS flag
Active OBRiboflavin (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 filledOralGm Pharmaceuticals2013-10-282017-03-31US flag
B-ComboRiboflavin (1 mg/1mL) + Dexpanthenol (1 mg/1mL) + Mecobalamin (1 mg/1mL) + Nicotinamide (1 mg/1mL) + Pyridoxine (1 mg/1mL) + Thiamine chloride (1 mg/1mL)InjectionIntramuscularPerdido Key Health And Wellness Inc2015-11-23Not applicableUS flag
BacminRiboflavin (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, coatedOralMarnel Pharmaceuticals, Llc2000-04-01Not applicableUS flag
Bal-Care DHARiboflavin (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)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUS flag
Bal-Care DHA EssentialRiboflavin (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)KitOralPru Gen Pharmaceuticals2012-05-01Not applicableUS flag
BiovitaRiboflavin (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)GranuleOralIldong Pharmaceutical Co., Ltd.2015-06-032019-09-13US flag
BiovitaRiboflavin (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)GranuleOralOASIS TRADING2018-12-25Not applicableUS flag
C-Nate DHARiboflavin (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 coatedOralCenturion Labs, LLC2013-01-01Not applicableUS flag
Cavan AlphaRiboflavin (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)KitOralSeton Pharmaceuticals2010-07-012013-09-30US flag

Categories

ATC Codes
A11HA04 — Riboflavin (vit b2)S01XA26 — Riboflavin
Drug Categories
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
  1. 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]
Human Metabolome Database
HMDB0000244
KEGG Drug
D00050
KEGG Compound
C00255
PubChem Compound
493570
PubChem Substance
46507342
ChemSpider
431981
BindingDB
50362895
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedHealth Services ResearchAcquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Lactic Acidosis / Lipodystrophies1
4CompletedTreatmentDiabetic Macular Edema (DME)1
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain (DPN)1
4CompletedTreatmentFatigue1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentPain1
4CompletedTreatmentPregnancy1
4CompletedTreatmentProgressive Keratoconus / Thin Corneas1
4CompletedTreatmentSmoking Addiction1
4RecruitingTreatmentProgressive Keratoconus1

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
FormRouteStrength
CapsuleOral0.2 mg
CapsuleOral300 mg
ElixirOral
TabletOral3 mg
TabletOral2 mcg
Tablet, chewableOral5 mg
TabletOral1500 IU
CapsuleOral0.4 mg
SyrupOral400 IU
SyrupOral0.35 mg
Tablet, coatedOral6.4 mg
Tablet, coatedOral300 mg
Capsule10 mcg
Capsule, liquid filledOral50 mg
Tablet, coatedOral10 mcg
TabletOral200 mcg
Tablet, coatedOral50 mcg
Tablet, sugar coatedOral2 mg
Injection, solution1 mg/1mL
Tablet, coatedOral10 mg
Injection, solutionIntravenous300 mcg/100mL
Tablet, sugar coatedOral50 mg
Tablet, coatedOral15 mg
SyrupOral5 mg/5ml
Solution2.5 mg/ml
Tablet, film coatedOral25 mg
Injection, solutionIntramuscular; Intravenous25 mg/2mL
Powder, for solutionIntramuscular; Intravenous
Tablet250 mg
Tablet, effervescentOral15 mg
CapsuleOral200 mg
CapsuleOral15 IU
Tablet, film coatedOral25 mcg
TabletOral4 mcg
Tablet, film coatedOral5 mcg
TabletOral50 mg
GranuleOral
TabletOral8.5 mg
TabletOral7.5 mg
TabletOral582.5 IU
TabletOral10 mcg
CapsuleOral2 mcg
CapsuleOral400 mcg
TabletOral100 mg
Capsule15 mg
SolutionOral50 mg
Tablet, chewableOral2 mcg
Tablet, chewableOral0.5 mg
Tablet, chewableOral1500 IU
Tablet, chewableOral0.25 mg
Tablet, chewableOral50 mg
Tablet, coatedOral3 mg
Tablet, coatedOral20 mg
SolutionIntramuscular50 mg
Tablet, coatedOral50 mg
SolutionIntramuscular300 mg
Tablet, coatedOral500 mcg
Capsule, liquid filledOral
CapsuleOral
SyrupOral200 iu/5mL
Tablet, film coated8000 IU
SyrupOral2000 IU/5ml
Capsule, coatedOral
Tablet4000 IU
Capsule4000 IU
TabletOral1 mg
TabletOral0.1 mg
Tablet, effervescentOral
Tablet, film coatedOral125 mg
TabletOral4000 IU
LiquidOral
CapsuleOral10 mg
Tablet, film coatedOral500 mg
CapsuleOral35 mg
TabletOral15 mg
Tablet, coatedOral60 mg
Tablet, coatedOral180 mg
Tablet, coatedOral37.75 mg
Capsule50 mg
LozengeOral
Syrup1.25 mg/1mL
SyrupOral
TabletOral6.5 mg
Capsule60 mg
Capsule, delayed releaseOral0.6 mg
Capsule, gelatin coatedOral40 mg
Tablet, delayed releaseOral
Tablet, extended releaseOral400 mcg
TabletOral18 mcg
Tablet, coatedOral100 mg
TabletOral2 mg
Injection, solution10 mg/2mL
SyrupOral1 g
Syrup12.5 mg/15mL
CapsuleOral5 mg
CapsuleOral50 mg
Tablet, coatedOral150 mcg
CapsuleOral4 mg
Tablet, film coatedOral800 mcg
Tablet, coatedOral
Capsule, liquid filledOral750 mcg
Tablet, chewableOral2500 IU
TabletOral300 mg
Capsule330 mg
InjectionIntramuscular
CapsuleOral6 mg
CapsuleOral500 mg
Tablet, coatedOral3.75 mg
Syrup400 iu/5mL
Tablet, coatedOral30 mg
Tablet, film coatedOral1200 mcg
TabletOral8.3 mg
CapsuleOral750 mcg
Injection, solutionIntramuscular; Intravenous50 mg/1mL
CapsuleOral5000 IU
SolutionIntravenous
TabletOral500 mg
Liquid; tabletOral
Tablet, chewableOral
LiquidIntravenous
Granule, effervescentOral
SolutionOral
Tablet, sugar coatedOral1 mg
SyrupOral2500 IU/5ml
CapsuleOral1828 µg
Capsule, liquid filledOral0.25 mg
TabletOral
CapsuleOral50 mcg
Tablet, coatedOral75 mg
Capsule, liquid filledOral0.6 mg
TabletOral2.5 mg
Tablet, orally disintegratingOral
Tablet, coatedOral250 mcg
Tablet, film coatedOral50 mg
Tablet, chewableOral200 mcg
TabletOral1.2 mg
LiquidOral2500 IU/5ml
CapsuleOral3000 IU
TabletOral150 mg
TabletOral5 mg
Capsule, delayed releaseOral150 mg
Tablet, coatedOral5 mg
SolutionOral100 mg
CapsuleOral2000 IU
Syrup5 mg/5mL
Syrup5 mg/100mL
TabletOral1.5 mg
CapsuleOral2667 IU
Tablet, effervescent0.15 mg
SyrupOral150 mg
Tablet, film coatedOral15 mg
SyrupOral1500 IU
Suspension / dropsOral
Solution / dropsOral
CapsuleOral4.2 mg
CapsuleOral4000 IU
Tablet, film coatedOral
Capsule, liquid filledOral0.1 mg
PillOral
TabletOral0.5 mg
Capsule, gelatin coatedOral
CapsuleOral0.1 mg
TabletOral5 mcg
TabletOral10 mg
TabletOral
Syrup1250 IU
Syrup150 ml
Capsule, liquid filledOral6 IU
SyrupOral1.7 mg/10ml
CapsuleOral25 mg
Tablet, chewableOral15 IU
CapsuleOral1 mg
CapsuleOral12 mg
Tablet, film coatedOral100 mcg
Injection, powder, lyophilized, for solutionIntravenous400 mcg
Solution2.5 mg
TabletOral40 mcg
Injection, solution5 g/100mL
Capsule, liquid filledOral1 mg
Injection, solutionIntravenous100 mg/100mL
Syrup100 iu/5mL
Capsule, extended releaseOral
Tablet, extended releaseOral
Powder, for solutionIntramuscular; Intravenous3500 IU
Capsule; liquidOral
Tablet, coatedOral25 mg
InjectionIntravenous1000 mg
Injection, solution50 mg/1mL
Tablet50 mg
SyrupOral0.25 mg/5ml
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous3500 IU
SolutionIntravenous5 g
CapsuleOral3.5 mg
Tablet, chewableOral5000 IU
Capsule, liquid filledOral25 mg
Syrup50 mg/5mL
Capsule, liquid filledOral200 mg
Tablet, extended releaseOral
Tablet, film coatedOral9.7 mg
CapsuleOral
SyrupOral1250 IU/5mL
Capsule75 mg
Tablet, chewableOral10 IU
Capsule, gelatin coatedOral0.5 mg
Injection, solution100 mg/1mL
Tablet, coatedOral2 mg
Tablet, coatedOral1 mg
Injection, solution14 mg/2mL
TabletOral25 mg
SyrupOral320 mg
KitOral
Tablet, chewableOral7.33 mg
Tablet, chewableOral1250 IU
Syrup20 mg/5mL
PowderOral
TabletOral200 mg
Tablet, film coatedOral200 mg
GranuleOral70 mcg
Prices
Unit descriptionCostUnit
Riboflavin powder0.44USD g
Riboflavin 100 mg tablet0.09USD tablet
Riboflavin 50 mg tablet0.08USD tablet
Vitamin b-2 50 mg tablet0.08USD tablet
Ribo 100 mg tablet0.04USD tablet
Vitamin b-2 25 mg tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)280 dec °CPhysProp
water solubility84.7 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-1.46HANSCH,C ET AL. (1995)
logS-3.68ADME Research, USCD
pKa10.2BUDAVARI,S ET AL. (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.657 mg/mLALOGPS
logP-1ALOGPS
logP-0.92ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)6.97ChemAxon
pKa (Strongest Basic)0.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.05 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.27 m3·mol-1ChemAxon
Polarizability37.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier-0.8495
Caco-2 permeable-0.7122
P-glycoprotein substrateSubstrate0.7414
P-glycoprotein inhibitor INon-inhibitor0.8708
P-glycoprotein inhibitor IINon-inhibitor0.9466
Renal organic cation transporterNon-inhibitor0.9279
CYP450 2C9 substrateNon-substrate0.7819
CYP450 2D6 substrateNon-substrate0.8435
CYP450 3A4 substrateNon-substrate0.522
CYP450 1A2 substrateInhibitor0.8531
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9516
CYP450 2C19 inhibitorInhibitor0.7302
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9203
Ames testNon AMES toxic0.804
CarcinogenicityNon-carcinogens0.7954
BiodegradationNot ready biodegradable0.9641
Rat acute toxicity1.6067 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9395
hERG inhibition (predictor II)Non-inhibitor0.5362
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.3 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-006x-4980000000-dd278a577316361d270a
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-004i-0019000000-86365dedafa031aa7787
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0006-4390000000-ac1b59ab7cc2209f4241
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-00dj-4900000000-72d33eb27b9bd6a13d9e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-004l-0569000000-874b71fdc78d04853bf0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0a4i-0091000000-a82c54d3153103fcdb1f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0a4i-0091000000-a82c54d3153103fcdb1f
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0090000000-2aff124ee1fc62c13844
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0090000000-f8b29c3e2c601a944a6c
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004l-0569000000-874b71fdc78d04853bf0
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0092000000-1f1be5508c1d50d8dff7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0092000000-74bf0b86efe72fe37198
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-057i-0069000000-bb0522be4472e049dbc5
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-057i-0069000000-208440cf501d0b9050d7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-006x-0029000000-8c3d72bf2a06d79bbd31
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-006x-0039000000-7d8dc991995cfc262ad1
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0092000000-4f524f1e6c8131751c92
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0560-0069000000-edc332be3fcbf6d0c14b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0009000000-2e6bf027d624900baabd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0239000000-659ca9fae9643f3ce73d
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. 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
  1. 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]
  2. 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
  1. 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]
  2. 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
  1. 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
  1. 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]
  2. 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
  1. 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 November 25, 2020 15:48

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