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

Similar Structures

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

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Indication

For the treatment of ariboflavinosis (vitamin B2 deficiency).

Associated Conditions

Associated Therapies

Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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

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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
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Acyclovir	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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Food Interactions

No interactions found.

Products

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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
B-2 Caps 100mg	Capsule		Oral	Twin Laboratories Inc.	1995-12-31	1999-11-10
B2 Tab 100mg	Tablet		Oral	Vita Health Products Inc	1979-12-31	2002-07-31
Riboflavin 5 Phosphate Cap 50mg	Capsule		Oral	Thorne Research Inc.	1985-12-31	2001-07-13
Riboflavin Tab 10mg	Tablet		Oral	Swiss Herbal Remedies Ltd.	1971-12-31	1999-09-09
Riboflavin Tab 5mg	Tablet		Oral	Stanley Pharmaceuticals, A Division Of Vita Health Products Inc.	1957-12-31	2002-07-31
RIBOFLAVIN TABLETS 10 MG.	Tablet	10 mg	Oral	บริษัท อินแพคฟาร์มา จำกัด	1995-02-24	2020-09-29
Riboflavin-S Tab 25mg	Tablet		Oral	Nutri West Products Ltd.	1993-12-31	1997-08-05
Vit B2 Ctr Srt 200mg	Tablet, extended release		Oral	Bioenergy Inc.	1979-12-31	1998-06-03
Vita-flavine Cap 100mg	Capsule		Oral	Les Laboratoires Vachon Inc.	1991-12-31	2001-08-07
Vitamin B-2	Capsule		Oral	Sisu Inc.	2001-09-01	2006-07-31

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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
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
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
Adeks - Dps	Riboflavin (0.6 mg) + Ascorbic acid (45 mg) + Beta carotene (1 mg) + Biotin (15 mcg) + Cyanocobalamin (4 mcg) + Nicotinamide (6 mg) + Panthenol (3 mg) + Phylloquinone (0.1 mg) + Pyridoxine hydrochloride (0.6 mg) + Thiamine (0.5 mg) + Vitamin A palmitate (1500 unit) + Vitamin D (400 unit) + Vitamin E (40 unit) + Zinc (5 mg)	Solution / drops	Oral	Axcan Pharma	1995-12-31	2007-10-01
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
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
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
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
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
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

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
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
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
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
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
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
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
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
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
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
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

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. [PubMed:8604671]

External Links

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 …

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MSDS

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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	Oral	0.2 mg
Capsule	Oral	300 mg
Elixir	Oral
Tablet, coated	Oral	2700 IU
Tablet	Oral	3 mg
Tablet	Oral	2 mcg
Tablet, chewable	Oral	5 mg
Tablet	Oral	1500 IU
Capsule	Oral	0.4 mg
Syrup	Oral	400 IU
Syrup	Oral	0.35 mg
Capsule, liquid filled	Oral	50 mg
Tablet	Oral	200 mcg
Tablet, sugar coated	Oral	2 mg
Tablet, sugar coated	Oral	50 mg
Tablet, coated	Oral	15 mg
Syrup	Oral	5 mg/5ml
Capsule		15 mg
Tablet, delayed release	Oral	15 mg
Solution		2.5 mg/ml
Tablet, film coated	Oral	25 mg
Injection, solution	Intramuscular; Intravenous	25 mg/2mL
Powder, for solution	Intramuscular; Intravenous
Tablet		250 mg
Tablet, effervescent	Oral	15 mg
Tablet	Oral	25 mg
Capsule	Oral	200 mg
Capsule	Oral	15 IU
Tablet, film coated	Oral	25 mcg
Tablet	Oral	4 mcg
Tablet, film coated	Oral	5 mcg
Granule	Oral
Tablet	Oral	8.5 mg
Tablet	Oral	7.5 mg
Tablet	Oral	582.5 IU
Tablet	Oral	10 mcg
Capsule	Oral	2 mcg
Capsule	Oral	400 mcg
Syrup	Oral	270 mg
Solution	Oral	50 mg
Tablet, chewable	Oral	2 mcg
Tablet, chewable	Oral	0.5 mg
Tablet, chewable	Oral	1500 IU
Tablet, chewable	Oral	0.25 mg
Tablet, chewable	Oral	50 mg
Tablet, coated	Oral	35 mg
Solution	Intramuscular	60 mg
Tablet, coated	Oral	20 mg
Elixir	Oral	200 mg
Granule	Oral	250 mg
Solution	Intramuscular	50 mg
Solution	Parenteral	300 mg
Syrup	Oral	175 mg
Tablet, coated	Oral	50 mg
Solution	Intramuscular	300 mg
Tablet, delayed release	Oral	50 mg
Capsule, liquid filled	Oral
Capsule	Oral
Syrup	Oral	130 mg
Tablet, film coated		8000 IU
Syrup	Oral	2000 IU/5ml
Capsule, coated	Oral
Tablet		4000 IU
Capsule		4000 IU
Tablet	Oral	10 mg
Tablet	Oral	1 mg
Tablet	Oral	0.1 mg
Tablet, effervescent	Oral
Tablet, film coated	Oral	125 mg
Tablet	Oral	4000 IU
Liquid	Oral
Capsule	Oral	10 mg
Tablet, film coated	Oral	500 mg
Tablet	Oral	50 mg
Powder, for solution	Intravenous	200 mg
Capsule	Oral	35 mg
Tablet	Oral	15 mg
Tablet, coated	Oral	180 mg
Syrup	Oral	0.18 g
Lozenge	Oral
Syrup	Oral
Tablet	Oral	6.5 mg
Capsule, delayed release	Oral	0.6 mg
Capsule, gelatin coated	Oral	40 mg
Tablet, delayed release	Oral
Tablet, extended release	Oral	400 mcg
Tablet	Oral	18 mcg
Tablet	Oral	2 mg
Syrup	Oral	1 g
Solution	Oral	444.4 mg
Capsule	Oral	5 mg
Capsule
Capsule	Oral	50 mg
Tablet, coated	Oral	150 mcg
Capsule	Oral	4 mg
Tablet, film coated	Oral	800 mcg
Tablet, coated	Oral
Tablet	Oral	14 mg
Syrup	Oral	133 mg
Capsule, liquid filled	Oral	750 mcg
Tablet, chewable	Oral	2500 IU
Tablet	Oral	300 mg
Injection	Intramuscular
Capsule	Oral	6 mg
Capsule	Oral	500 mg
Tablet, film coated	Oral	1200 mcg
Tablet	Oral	8.3 mg
Capsule	Oral	750 mcg
Syrup	Oral	0.37 g
Capsule	Oral	5000 IU
Solution	Intravenous
Tablet	Oral	500 mg
Liquid; tablet	Oral
Tablet, chewable	Oral
Liquid	Intravenous
Granule, effervescent	Oral
Solution	Oral
Tablet, sugar coated	Oral	1 mg
Syrup	Oral	2500 IU/5ml
Capsule	Oral	1828 µg
Capsule, liquid filled	Oral	160 mg
Tablet	Oral
Capsule, liquid filled	Oral	0.6 mg
Tablet	Oral	2.5 mg
Powder, for solution	Oral	20 mg
Tablet, orally disintegrating	Oral
Tablet, film coated	Oral	50 mg
Tablet, chewable	Oral	200 mcg
Tablet	Oral	1.2 mg
Liquid	Oral	2500 IU/5ml
Capsule	Oral	3000 IU
Tablet	Oral	150 mg
Tablet	Oral	5 mg
Capsule, delayed release	Oral	70 mg
Solution	Oral	100 mg
Capsule	Oral	2000 IU
Tablet	Oral	1.5 mg
Capsule	Oral	2667 IU
Capsule	Oral	50 mcg
Syrup	Oral	150 mg
Tablet, film coated	Oral	15 mg
Syrup	Oral	1500 IU
Suspension / drops	Oral
Solution / drops	Oral
Capsule, coated	Oral	400 cg
Capsule	Oral	4.2 mg
Capsule	Oral	4000 IU
Tablet, film coated	Oral
Pill	Oral
Tablet	Oral	0.5 mg
Syrup	Oral	370 mg
Capsule, gelatin coated	Oral
Capsule	Oral	0.1 mg
Tablet	Oral	5 mcg
Tablet	Oral
Syrup		1250 IU
Syrup		150 ml
Capsule, liquid filled	Oral	6 IU
Syrup	Oral	1.7 mg/10ml
Capsule	Oral	25 mg
Tablet, chewable	Oral	15 IU
Capsule	Oral	1 mg
Capsule	Oral	12 mg
Tablet, film coated	Oral	100 mcg
Powder, for solution	Oral	421 mcg
Injection, powder, lyophilized, for solution	Intravenous	400 mcg
Solution		2.5 mg
Tablet	Oral	40 mcg
Capsule, extended release	Oral
Tablet, extended release	Oral
Powder, for solution	Intramuscular; Intravenous	3500 IU
Capsule; liquid	Oral
Injection	Intravenous	1000 mg
Capsule, liquid filled	Oral	1 mg
Powder, for solution	Oral
Tablet		50 mg
Syrup	Oral	0.25 mg/5ml
Injection, powder, lyophilized, for solution	Intramuscular; Intravenous	3500 IU
Solution	Intravenous	5 g
Capsule	Oral	3.5 mg
Tablet, chewable	Oral	5000 IU
Syrup	Oral	100 mg
Capsule, liquid filled	Oral	25 mg
Capsule, liquid filled	Oral	200 mg
Tablet, extended release	Oral
Capsule, liquid filled	Oral	18.375 mg
Tablet, film coated	Oral	9.7 mg
Syrup	Oral	400 mg
Capsule	Oral
Syrup	Oral	1250 IU/5mL
Tablet, chewable	Oral	10 IU
Capsule, gelatin coated	Oral	0.5 mg
Syrup	Oral	320 mg
Kit	Oral
Tablet, chewable	Oral	7.33 mg
Tablet	Oral	100 mg
Tablet, chewable	Oral	1250 IU
Powder	Oral
Tablet	Oral	200 mg
Tablet, film coated	Oral	200 mg
Granule	Oral	70 mcg
Solution
Tablet
Tablet, sugar coated	Oral
Solution

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (11.3 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-006x-4980000000-dd278a577316361d270a
MS/MS Spectrum - Quattro_QQQ 10V, Positive	LC-MS/MS	splash10-004i-0019000000-86365dedafa031aa7787
MS/MS Spectrum - Quattro_QQQ 25V, Positive	LC-MS/MS	splash10-0006-4390000000-ac1b59ab7cc2209f4241
MS/MS Spectrum - Quattro_QQQ 40V, Positive	LC-MS/MS	splash10-00dj-4900000000-72d33eb27b9bd6a13d9e
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	LC-MS/MS	splash10-004l-0569000000-874b71fdc78d04853bf0
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	LC-MS/MS	splash10-0a4i-0091000000-a82c54d3153103fcdb1f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negative	LC-MS/MS	splash10-0a4i-0091000000-a82c54d3153103fcdb1f
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-0a4i-0090000000-2aff124ee1fc62c13844
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-0a4i-0090000000-f8b29c3e2c601a944a6c
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-0a4i-0090000000-4e8c9bd38ea0f5ae9a94
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-004l-0569000000-874b71fdc78d04853bf0
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0006-0092000000-1f1be5508c1d50d8dff7
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0006-0092000000-74bf0b86efe72fe37198
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-057i-0069000000-bb0522be4472e049dbc5
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-057i-0069000000-208440cf501d0b9050d7
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-006x-0029000000-8c3d72bf2a06d79bbd31
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-006x-0039000000-7d8dc991995cfc262ad1
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0006-0092000000-4f524f1e6c8131751c92
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0560-0069000000-edc332be3fcbf6d0c14b
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0006-0009000000-2e6bf027d624900baabd
MS/MS Spectrum - , positive	LC-MS/MS	splash10-004i-0239000000-659ca9fae9643f3ce73d
1H NMR Spectrum	1D NMR	Not Applicable
[1H,13C] 2D NMR Spectrum	2D NMR	Not Applicable

Targets

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Details1. Riboflavin kinase

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]

Details2. Riboflavin synthase

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]

Details3. Flavin reductase (NADPH)

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

Details1. Amine oxidase [flavin-containing] A

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]

Details2. Methylenetetrahydrofolate reductase

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

Details1. Solute carrier family 22 member 6

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 13:24 / Updated on March 04, 2021 11:02

Riboflavin

Identification

Structure for Riboflavin (DB00140)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Targets

References

References

References

Enzymes

References

References

Transporters

References