Identification

Name
Riboflavin
Accession Number
DB00140  (NUTR00010, APRD00626, EXPT02760, DB09358)
Type
Small Molecule
Groups
Approved, Nutraceutical, Vet Approved
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. [PubChem]

Structure
Thumb
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
  • E101
  • Lactoflavin
  • Lactoflavine
  • Riboflavina
  • Riboflavine
  • Riboflavinum
  • Vitamin B2
  • Vitamin G
External IDs
INS NO. 101(I) / NCI-0033298 / NSC-33298
Product Ingredients
IngredientUNIICASInChI Key
Riboflavin 5'-phosphate sodium20RD1DZH996184-17-4LQVGUKOCMOKKJU-QPVGXXQTSA-M
Riboflavin 5'-phosphate sodium anhydrous957E53WV42130-40-5OHSHFZJLPYLRIP-BMZHGHOISA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PhotrexaSolution / drops1.46 mg/mLOphthalmicAvedro, Inc.2016-04-15Not applicableUs
Photrexa ViscousSolution / drops1.46 mg/mLOphthalmicAvedro, Inc.2016-04-15Not applicableUs
Riboflavin Inj 50mg/mlSolution50 mgIntramuscular; IntravenousKripps Pharmacy Ltd.1979-12-31Not applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
B-2 Caps 100mgCapsule100 mgOralTwin Laboratories Inc.1995-12-311999-11-10Canada
B2 Tab 100mgTablet100 mgOralVita Health Products Inc1979-12-312002-07-31Canada
Riboflavin 5 Phosphate Cap 50mgCapsule50 mgOralThorne Research Inc.1985-12-312001-07-13Canada
Riboflavin Tab 10mgTablet10 mgOralSwiss Herbal Remedies Ltd.1971-12-311999-09-09Canada
Riboflavin Tab 5mgTablet5 mgOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada
Riboflavin-S Tab 25mgTablet25 mgOralNutri West Products Ltd.1993-12-311997-08-05Canada
Vit B2 Ctr Srt 200mgTablet, extended release200 mgOralBioenergy Inc.1979-12-311998-06-03Canada
Vita-flavine Cap 100mgCapsule100 mgOralLes Laboratoires Vachon Inc.1991-12-312001-08-07Canada
Vitamin B-2Capsule100 mgOralSisu Inc.2001-09-012006-07-31Canada
Vitamin B-2 50 Mg TabletsTablet50 mgOralGeneral Nutrition Canada Inc.1997-04-182006-08-03Canada
International/Other Brands
Bisulase
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Active FERiboflavin (4 mg/1) + Beta carotene (2100 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (1 mg/1) + Cyanocobalamin (30 ug/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) + Vitamin C (160 mg/1) + Vitamin E (40 [iU]/1) + Zinc oxide (20 mg/1)TabletOralGm Pharmaceuticals2013-11-11Not applicableUs
Adult Infuvite Multiple VitaminsRiboflavin 5'-phosphate sodium (3.6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
Adult Infuvite Multiple VitaminsRiboflavin 5'-phosphate sodium (3.6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsRiboflavin 5'-phosphate sodium (3.6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsRiboflavin 5'-phosphate sodium (3.6 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Phylloquinone (150 ug/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
AlertonicRiboflavin (.111 mg) + Choline (2.222 mg) + Inositol nicotinate (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
AlertonicRiboflavin (0.111 mg) + Choline (2.222 mg) + Inositol nicotinate (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
Allbee With C 550 CapRiboflavin (10 mg) + Nicotinamide (50 mg) + Calcium pantothenate (10 mg) + Pyridoxine hydrochloride (5 mg) + Thiamine mononitrate (15 mg) + Vitamin C (550 mg)CapsuleOralWhitehall Robins Inc.1994-12-312003-08-01Canada
Allbee With Vitamin C CapRiboflavin (10 mg) + Nicotinamide (50 mg) + Calcium pantothenate (10 mg) + Pyridoxine hydrochloride (5 mg) + Thiamine mononitrate (15 mg) + Vitamin C (300 mg)CapsuleOralWhitehall Robins Inc.1994-12-312000-07-26Canada
Alsimine W Vitamins A DRiboflavin 5'-phosphate sodium (2 mg) + Calcium (13 mg) + Cyanocobalamin (10 mcg) + Dexpanthenol (5 mg) + Dexpanthenol (400 unit) + Ferrous gluconate (16 mg) + Nicotinamide (40 mg) + Pyridoxine hydrochloride (3 mg) + Thiamine Hydrochloride (4.5 mg) + Vitamin A (10000 unit)Capsule; LiquidOralAlsi Cie Ltee1978-12-312003-05-21Canada
Categories
UNII
TLM2976OFR
CAS number
83-88-5
Weight
Average: 376.3639
Monoisotopic: 376.138284392
Chemical Formula
C17H20N4O6
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

Pharmacology

Indication

For the treatment of ariboflavinosis (vitamin B2 deficiency).

Structured Indications
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
Human
ARiboflavin synthase
other
Escherichia coli (strain K12)
AFlavin reductase (NADPH)
product of
Human
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Riboflavin MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Porfimer sodiumRiboflavin may increase the photosensitizing activities of Porfimer sodium.Approved, Investigational
VerteporfinRiboflavin may increase the photosensitizing activities of Verteporfin.Approved, Investigational
Food Interactions
Not Available

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]
External Links
Human Metabolome Database
HMDB00244
KEGG Drug
D00050
KEGG Compound
C00255
PubChem Compound
493570
PubChem Substance
46507342
ChemSpider
431981
BindingDB
50362895
ChEBI
17015
ChEMBL
CHEMBL1534
PharmGKB
PA451242
HET
RBF
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Riboflavin
ATC Codes
A11HA04 — Riboflavin (vit b2)
AHFS Codes
  • 88:08.00 — Vitamin B Complex
PDB Entries
1bu5 / 1hze / 1i18 / 1kyv / 1l5r / 1mog / 1nb9 / 1pkv / 1t6z / 2a58
show 26 more
MSDS
Download (39.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections / Infection, Human Immunodeficiency Virus I / Mycobacterium avium complex infection1
1CompletedDiagnosticHealthy Volunteers1
1CompletedPreventionHIV-infection/Aids1
1CompletedTreatmentCancers / Metastases1
1CompletedTreatmentUlcerative keratitis1
1Not Yet RecruitingBasic ScienceAging / Mineral deficiency / Vitamin Deficiency1
1, 2RecruitingOtherHypercholesterolemia, Familial / Hypertriglyceridemias1
1, 2RecruitingPreventionKeratolysis1
1, 2RecruitingTreatmentAutoimmune Diseases / Chemical Injuries / Lupus Erythematosus, Systemic / Ocular Cicatricial Pemphigoid / Other Autoimmune Diseases / Rheumatoid Arthritis / Stevens Johnson Syndrome / Unspecified Complication of Corneal Transplant1
1, 2SuspendedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
2Active Not RecruitingTreatmentKeratoconus1
2Active Not RecruitingTreatmentKeratoconus / Post-Refractive Ectasia1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentCancer, Breast1
2CompletedTreatmentCentral Serous Chorioretinopathy (CSC)1
2RecruitingBasic ScienceAlcohol Drinking / Controlled1
2RecruitingPreventionAmnestic / Cognitive Disorders / Delayed Emergence From Anesthesia / Delirium / Delirium, Dementia / Delirium, Dementia, Amnestic, Cognitive Disorders1
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kidney Diseases1
2RecruitingTreatmentPsoriasis1
2RecruitingTreatmentSports-related Concussion1
2Unknown StatusTreatmentCorneal Ectasia / Ectasia / Keratoconus1
2Unknown StatusTreatmentMyocardial Infarction (MI)1
2WithdrawnOtherCompliance / Pain, Chronic1
2, 3CompletedTreatmentAcidosis, Respiratory1
2, 3CompletedTreatmentCardiovascular Disease (CVD) / Chronic Kidney Disease (CKD) / Mortality1
2, 3Unknown StatusTreatmentEctasia / Keratoconus1
2, 3WithdrawnTreatmentCorneal Ectasia / Progressive Keratoconus1
3Active Not RecruitingTreatmentCorneal Ectasia / Keratoconus3
3CompletedPreventionComplications, Pregnancy / Human Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionCoronary Artery Bypass Grafting (CABG) Surgery / Left Ventricular Dysfonction1
3CompletedTreatmentAnemias1
3CompletedTreatmentDiarrheal Illnesses / Growth Faltering / Respiratory Illness1
3CompletedTreatmentEctasia1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Tuberculosis, Pulmonary1
3CompletedTreatmentHydatidiform Mole1
3CompletedTreatmentKeratoconus3
3CompletedTreatmentProgressive Keratoconus1
3RecruitingTreatmentCrohn's Disease (CD) / Oral Ulcers1
3RecruitingTreatmentKeratoconus1
3TerminatedNot AvailableKeratoconus and Ectasia1
3TerminatedTreatmentCorneal Ectasia / Keratoconus1
3TerminatedTreatmentEctasia1
3TerminatedTreatmentKeratoconus2
3TerminatedTreatmentMultiple System Atrophy (MSA)1
3Unknown StatusNot AvailableAnemias / Low Birth Weight / Neonatal Mortality1
3Unknown StatusTreatmentAlzheimer's Disease (AD) / Down Syndrome (DS)1
3Unknown StatusTreatmentUnstable Corneas1
4CompletedHealth Services ResearchAcidosis, Respiratory / Acquired Immune Deficiency Syndrome (AIDS) / Human Immunodeficiency Virus (HIV) Infections / Lipodystrophies1
4CompletedTreatmentDiabetic Peripheral Neuropathic Pain1
4CompletedTreatmentHyperemesis Gravidarum / Morning Sickness / Nausea / Pregnancy / Vomiting1
4CompletedTreatmentPregnancy1
4CompletedTreatmentProgressive Keratoconus / Thin Corneas1
4CompletedTreatmentSmoking Addiction1
4Enrolling by InvitationTreatmentKeratoconus / Keratoconus, Unstable1
4RecruitingTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4WithdrawnTreatmentNephritis / Proteinuria / Systemic Lupus Erythematosus (SLE)1
Not AvailableCompletedNot AvailableFruste Keratoconus / Risk of Ectasia1
Not AvailableCompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedPreventionNeural Tube Defects (NTDs)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentSports Related Concussion1
Not AvailableRecruitingTreatmentEctasia / Keratoconus1
Not AvailableRecruitingTreatmentTemporomandibular Joint Disorders1
Not AvailableTerminatedTreatmentInfectious Keratitis1
Not AvailableUnknown StatusPreventionBrittle Cornea Syndrome / Ehlers-Danlos Syndrome Type 61
Not AvailableWithdrawnPreventionHuman Immunodeficiency Virus (HIV) Infections1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
ElixirOral
Tablet, extended releaseOral
InjectionIntramuscular
Injection, solutionIntramuscular; Intravenous
Powder, for solutionIntramuscular; Intravenous
Powder, for solutionIntravenous
GranuleOral
Capsule, liquid filledOral
CapsuleOral
Tablet, effervescentOral
SyrupOral
Capsule, gelatin coatedOral
LiquidIntramuscular; Intravenous
PowderOral
Tablet, chewableOral
LiquidIntravenous
Injection, powder, lyophilized, for solutionIntravenous
Liquid; tabletOral
Solution / dropsOral
Injection, solution, concentrateIntravenous
SolutionIntravenous
Granule, effervescentOral
LiquidOral
SolutionOral
SolutionIntramuscular; Intravenous
Injection, solutionIntravenous
Solution / dropsOphthalmic1.46 mg/mL
TabletOral
Kit
Tablet, coatedOral
CapsuleOral50 mg
SolutionIntramuscular; Intravenous50 mg
TabletOral10 mg
TabletOral5 mg
TabletOral25 mg
KitOral
Capsule, extended releaseOral
Capsule; liquidOral
LozengeOral
Tablet, extended releaseOral200 mg
CapsuleOral100 mg
InjectionIntramuscular; Intravenous
InjectionIntravenous
TabletOral50 mg
TabletOral100 mg
TabletOral4 mg
Tablet, film coatedOral
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

Taxonomy

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
Flavin / Diazanaphthalene / Quinoxaline / Pyrimidone / Pyrazine / Pyrimidine / Benzenoid / Heteroaromatic compound / Vinylogous amide / Secondary alcohol
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
flavin (CHEBI:17015) / Water-soluble vitamins (C00255)

Targets

Kind
Protein
Organism
Human
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
Human
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
Human
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
Human
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
Human
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 December 10, 2017 17:18