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Identification
NameRiboflavin
Accession NumberDB00140  (NUTR00010, APRD00626, EXPT02760, DB09358)
TypeSmall Molecule
GroupsApproved, 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 Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Riboflavin Inj 50mg/mlsolution50 mgintramuscular; intravenousKripps Pharmacy Ltd.1979-12-31Not applicableCanada
Vit B2 Ctr Srt 200mgtablet (extended-release)200 mgBioenergy Inc.1979-12-311998-06-03Canada
Generic Prescription ProductsNot Available
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 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
Vita-flavine Cap 100mgcapsule100 mgoralLes Laboratoires Vachon Inc.1991-12-312001-08-07Canada
Vitamin B-2 50 Mg Tabletstablet50 mgoralGeneral Nutrition Canada Inc.1997-04-182006-08-03Canada
Vitamin B-2 Riboflavin 100mg Capsulescapsule100 mgoralAlbi Naturals1999-04-302009-07-15Canada
Vitamin B2 100 mgcapsule100 mgoralFlora Manufacturing And Distributing Ltd.2002-03-152004-08-04Canada
Vitamin B2 100mgtablet100 mgoralGreat Earth Companies, Inc.1998-08-252002-10-02Canada
Vitamin B2 Tab 100mgtablet100 mgoralQuest Vitamins A Div Of Purity Life Health Products1978-12-312001-07-06Canada
Vitamin B2 Tab 4mg USP Chewabletablet4 mgoralLab Gernetic Int Ltee1985-12-311997-02-21Canada
Vitamin B2 Tablets 100mgtablet100 mgoralNu Life Nutrition Ltd.1987-12-312005-03-15Canada
International Brands
NameCompany
BisulaseNot Available
Brand mixtures
NameLabellerIngredients
Allbee With C 550 CapWhitehall Robins Inc.
Allbee With Vitamin C CapWhitehall Robins Inc.
Am CapsNew Vision Nutritionals Company
AntlervironClassical Remedia Ltd
AppedrineChattem Canada
B 6 PlusAnabolic Laboratories Inc.
B C Antistress CapLes Laboratoires Bio SantÉ Inc.
B Complex 25mg Vitamin SupplementGarden State Nutritionals
B Complex 50 Vitamin CapBioforce Canada Inc.
B Complex 500 TabNobel Pharm Enr.
B Complex Plus C 300mg TabNutricorp International
B Complex TabletsGolden Neo Life Diamite International, Limited
B Complex W C and B12 InjE L Stickley And Co Ltd.
B Complex W C Forte CapEverest Pharmaceuticals Ltd.
B Complex W Vitamin C Fortis CapShoppers Drug Mart Inc.
B Complex With C 300mgVita Health Products Inc
B Complex With C 550mgVita Health Products Inc
B Compound 50mg TabGahler Enterprises Ltd.
B Totum 500Desbergers LtÉe, Division Of Technilab Inc.
B VirolRolmex International Inc.
B Vitamin Compound With B12 ThunasThuna Herbal Remedies Ltd.
B-100 Complex TabletsViva Pharmaceutical Inc.
B-100 Vitamin SupplementGarden State Nutritionals
B-2 100mg With C 20mgGahler Enterprises Ltd.
B-plex 100Merit Pharmaceutical
B-plus - TabChampion's Choice Advanced Nutrition Inc.
B50 B Complex TabNutristar Health Products (1987) Inc.
B6 Plus TabVita Health Products Inc
BacminMarnel Pharmaceuticals, Inc.
Balanced B 125 SrtAnabolic Laboratories Inc.
Beminal W C Fortis InjAyerst Laboratories
Bev 29 TabBeverly International Nutrition
Biovim TabLe Naturiste J.M.B. Inc.
BiovitaIldong Pharmaceutical Co., Ltd.
Bugs Bunny and Friends Multiple VitaminsBayer Inc Consumer Care
Bugs Bunny Chew Multi Vit Plus IronMiles Canada Inc. Consumer Health Care Division
C-B ComplexAvacare, Division Of Jeunique International Inc.
C.A.G. TabNutrition For Life International
Cc IIAdded Dimensions
Cda-21 Vitamins With Non-medicinal Probiotic ComplexRx Vitamins Inc.
Cedevita Plus Vitamin SupplementPliva, Pharmaceutical, Chemical, Food And Cosmetic Industry, Inc.
Cedevita Sugar-free Vitamin SupplementPliva, Pharmaceutical, Chemical, Food And Cosmetic Industry, Inc.
Chela Potassium PlusNu Life Nutrition Ltd.
Chela-chromium 200Nu Life Nutrition Ltd.
Chew.multiple Vits.with Extra C for ChildrenRandle Pharmaceutical Inc.
Chewable Multiple Vit Plus Iron for ChildrenRandle Pharmaceutical Inc.
Chewable Multiple Vitamins for ChildrenRandle Pharmaceutical Inc.
Chewable Multiple Vitamins Plus Extra CRandle Pharmaceutical Inc.
Chewable Multiple Vitamins Plus Iron TabRandle Pharmaceutical Inc.
Chewable Multiple Vitamins TabRandle Pharmaceutical Inc.
Chewable MultivitaminsWn Pharmaceuticals Ltd.
Chewable Multivitamins Plus IronWn Pharmaceuticals Ltd.
Children's Chewable Multiple Vit.plus IronStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Children's Chewable Multiple Vitamins - TabStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Children's Chewable Multiple Vitamins (chewable Tablets)Pharmetics (2011) Inc
Children's Chewable Multiple Vitamins With Extra Vitamin C (chewable Tablets)Pharmetics (2011) Inc
Children's Chewable Multiple Vitamins With Iron Tablets (chewable Tablets)Pharmetics (2011) Inc
Childrens Chew Multi Vitamin TabNutristar Health Products (1987) Inc.
Childrens Chewable MultivitaminsRandle Labs Inc.
Childrens Chewable Multivitamins W IronRandle Labs Inc.
Childrens Chewable VitaminsD.C. Labs Limited
Childrens Multiple Vit and Min Chew TabCountry Health Laboratories Ltd.
Citranatal DHAMission Pharmacal Company
Citranatal RxMission Pharmacal Company
Complete Mega BGahler Enterprises Ltd.
Complexe B 75mgPharmalab Inc.
Complexe B Compose 75Les Laboratoires Bio SantÉ Inc.
Concept DHAUs Pharmaceutical Corporation
Concept ObUs Pharmaceutical Corporation
Croq-vit Pour EnfantsNutrivac Ltee
Dexatrim TabletsChattem Canada
Dia-viteR & D Laboratories Inc.
Dynam Ampoule Et TabletCardinaux Enrg Les Produits Naturels
EscaviteGm Pharmaceuticals, Inc.
Everyday Multiple VitaminsD.C. Labs Limited
Everyday Multiple Vitamins With IronD.C. Labs Limited
Ez-flexMetagenics, Inc.
Ferra Naka Plus VitaminsNaka Sales Ltd.
Flinstones Multiple Plus IronMiles Canada Inc. Consumer Health Care Division
Flintstones Multiple VitaminsBayer Inc Consumer Care
Flintstones Multiple Vitamins Plus IronBayer Inc Consumer Care
Flintstones Multiple Vitamins TabMiles Canada Inc. Consumer Health Care Division
Flintstones W Extra C TabMiles Canada Inc. Consumer Health Care Division
Floradix Formula LiqFlora Manufacturing And Distributing Ltd.
Floravit - SyrFlora Manufacturing And Distributing Ltd.
FlorivaBon Geo Pharmaceuticals, Inc.
Floriva PlusBon Geo Pharmaceuticals, Inc.
Folcaps Care OneMidlothian Laboratories
For Kids Only Chewable Multivit. Plus IronKsl Pharmaceuticals
For Kids Only Chewable Multivitamins - TabKsl Pharmaceuticals
Formula Adr-vitamin B2,b6 W Calpan TabMetagenics, Inc.
Formula CnBalance Plus, Inc.
Formula Fm Vitamins & Minerals TabMetagenics, Inc.
Formula Pro-BBalance Plus, Inc.
Fortaplex InjKripps Pharmacy Ltd.
Gemvites Jr Tab ChewablePharmavite Laboratories (1987) Inc.
Globucel - MethodeLes Laboratoires Swisse Inc.
Harvest Of Values All B Complex TabHillestad Pharmaceuticals Usa
Hemarexin AmpLab Bio Chimique Inc.,Division Of Technilab Pharma Inc.
Hemenatal ObWh Nutritionals, Llc
Hi Potency B Complex W Chelated MineralsKlaire Labs Inc.
Hi Potency B52 B Complex TabCountry Health Laboratories Ltd.
Hi Potency Stress B Tension With CLee Adams Laboratories
High Potency Vitamin B Complex + C TabVita Health Products Inc
Iberet 500Abbott Laboratories, Limited
Infantol DropsChurch & Dwight Canada Corp
Integra PlusUs Pharmaceutical Corporation
Iron Polysaccharides Folic Acid DHAVirtus Pharmaceuticals LLC
Isotonix Advanced B-complex Vitamins With Potassium and MagnesiumMarket America, Inc.
Isotonix Calcium Plus FormulaMarket America, Inc.
Isotonix Vitamin B-folic Acid-mineral SuppleMarket America, Inc.
Kimchi Vitamin Chewable MultivitaminTobico
KindervitesHerbalife International Of America, Inc.
Lipo-B-C TabMetagenics, Inc.
Liqui B ComplexTwin Laboratories Inc.
Liqui B Complex PlusTwin Laboratories Inc.
Liqui Infant VitaminsTwin Laboratories Inc.
Liqui VitaTwin Laboratories Inc.
Liquid B Complex 50Jamieson Laboratories Ltd
Livron Plus AmpouleMedic Laboratory LtÉe
Livron Plus TabMedic Laboratory LtÉe
Lysamine Diet Supp Amp-tabWelcker Lyster Ltd., Division Of Technilab Inc.
M.V.I. PaediatricAventis Pharma Inc
M.V.I. PediatricHospira Worldwide, Inc.
Maltlevol 12 LiqCarter Horner Corp.
Maltlevol LiqCarter Horner Corp.
Megavites TabIcn Canada Ltd.
Meplex T 750Medic Laboratory LtÉe
Mini-B TabTwin Laboratories Inc.
Multi BSeroyal International Inc.
Multi Enfants TabVitalab
Multi RolRolmex International Inc.
Multi Vitamin and FluorideLibertas Pharma, Inc.
Multi Vitamin Drops With FluorideSeton Pharmaceuticals
Multi Vitamin Drops With Fluoride and IronSeton Pharmaceuticals
Multi Vitamin Drops With Fluoride With IronStratus Pharmaceuticals
Multi Vitamin With FluorideQualitest Pharmaceuticals
Multi Vitamin, Iron and FluorideLibertas Pharma, Inc.
Multi Vite Liq AdultPharmetics (2011) Inc
Multi Vite Liq JuniorPharmetics (2011) Inc
Multi-min Electro C Pow Plus B2Quest Vitamins A Div Of Purity Life Health Products
Multi-vit With FluorideQualitest Pharmaceuticals
Multi-vit With Fluoride and IronQualitest Pharmaceuticals
Multi-vitaminLLC Federal Solutions
Multi-vitamin FluorideStratus Pharmaceuticals
Multi-vitamin Fluoride and Iron DropsBoca Pharmacal, LLC
Multi-vitamin Fluoride DropsH.J. Harkins Company, Inc.
Multi-vitamin With FluorideGolden State Medical Supply, Inc.
Multiple Vitamin TabAdams Labs Ltd.
Multiple Vitamins and Minerals TabRandle Labs Inc.
Multiple Vitamins TabRandle Labs Inc.
MultisolLes Laboratoires Vachon Inc.
Multivit-liqPharmalab Inc.
MultivitaminLaboratoires Confab Inc
Multivitamin With FluorideSancilio & Company Inc
MultivitaminesRolmex International Inc.
Multivitamines Et MinerauxLe Groupe M. Vachon Inc.
Multivitamines Plus Fer Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamines Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamins W IronRandle Labs Inc.
MvcSancilio & Company Inc
Mvc-fluorideSancilio & Company Inc.
Mynephrocaps Dialysis/stress Vitamin SupplementMartin Ekwealor Pharmaceuticals, Inc.
Nata KompleteWh Nutritionals, Llc
NatafortMission Pharmacal Company
Neo Vites TabNeolab Inc
Neo-bexNeolab Inc
Neo-bex InjectableBrostel Inc.
NephrocapsCardinal Health
O-cal Fa MultivitaminPharmics, Inc.
O-cal Prenatal VitaminPharmics, Inc.
Orange Flavored Crystal Chews TabJeunique International Inc.
Orifer FSanofi Aventis Canada Inc
Orti BSeroyal International Inc.
Permathene-12 - CapletCCA Industries, Inc.
Phosthenine Vitamines Et Fer (ampoules Buvable)Laboratoires Cortunon Inc.
Phytofortis + Calcium A-DProduits Phyto Inc.
Phytoplex B LiqProduits Phyto Inc.
Pnv Ferrous Fumarate Docusate Folic AcidVirtus Pharmaceuticals LLC
Pnv Prenatal Plus MultivitaminSancilio & Company Inc
Pnv Prenatal VitaminSancilio & Company Inc
Pnv Prenatal Vitamin Plus Vitamin ASancilio & Company Inc
Pnv-firstAcella Pharmaceuticals, LLC
Pnv-selectAcella Pharmaceuticals, LLC
Prefera Ob Plus DHAAlaven Pharmaceutical LLC
PreferaobMEDA Pharmaceuticals
Preferaob Plus DHAAlaven Pharmaceutical LLC
Prenatal 19Nationwide Laboratories, LLC
Prenatal Mega AntioxidantUsana Health Services, Inc.
Prenatal PlusBlenheim Pharmacal, Inc.
Prenatal Vitamins Plusbryant ranch prepack
Prenatal Vitamins Plus Low IronPatrin Pharma, Inc.
Prenate EliteAvion Pharmaceuticals, Llc
Prenate StarAvion Pharmaceuticals, Llc
PreplusVirtus Pharmaceuticals LLC
PretabVirtus Pharmaceuticals LLC
Prevital TabBio Vita
Purevit Dualfe PlusPure Tek Corporation
Reaphirm Plant Source DHAEverett Laboratories, Inc.
Reno CapsNnodum Pharmaceuticals
Revit TabIcn Canada Ltd.
Se-natal 19Seton Pharmaceuticals
Se-natal 19 ChewableSeton Pharmaceuticals
Se-natal OneSeton Pharmaceuticals
Se-tan PlusSeton Pharmaceuticals
Sopalamine/3b Plus CTechnilab Pharma Inc.
Stress B&c TabBioforce Canada Inc.
Stress TabVita Health Products Inc
Stress TabletsD.C. Labs Limited
StressmatesTwin Laboratories Inc.
Strovite Forte CapletEverett Laboratories, Inc.
Strovite One CapletsEverett Laboratories, Inc.
Super B Compound W 500mg Vit CGahler Enterprises Ltd.
Super PantoplexNu Life Nutrition Ltd.
Supravite Pour EnfantsPharmalab Inc.
Surbex 500 FilmtabAbbott Laboratories, Limited
Surbex-500 With IronAbbott Laboratories, Limited
Swical-energy-2Les Laboratoires Swisse Inc.
Tandem ObUs Pharmaceutical Corporation
Tandem PlusUs Pharmaceutical Corporation
Time Release B 100 Compound - TabletHealth Wise Nutrition Inc.
Tini-cal AmpoulesPharmetics (2011) Inc
Toni Com LiqVitalab
Tonimol Cap LiqHerbes Universelles Inc.
TriadvanceTrigen Laboratories, Inc.
Tricare PrenatalMedecor Pharma, Llc
Trinatal GtTrigen Laboratories, Inc.
Twin Ultra Liquid Fruit Punch FlavorTwin Laboratories Inc.
Twin Ultra Liquid Grape FlavorTwin Laboratories Inc.
Twin Ultra Liquid Lemon-lime FlavorTwin Laboratories Inc.
Twin Ultra Liquid Orange FlavorTwin Laboratories Inc.
Ultimatecare One NfTrigen Laboratories, Inc.
Ultra EnerforceNutribon (1986) Inc.
Ultra HrNatural Organics Inc.
V-natalVirtus Pharmaceuticals
Vasodyn TabNutri Dyn Products Ltd.
Viamon Ampoules Et ComprimesLab Nadeau LtÉe, Division Of Technilab Inc.
Virt-bal DHA PlusVirtus Pharmaceuticals
Virt-capsVirtus Pharmaceuticals LLC
Virt-PNVirtus Pharmaceuticals
Virt-vite PlusVirtus Pharmaceuticals LLC
Vit B Complex Plus Vit C 550mgHall Laboratories, Ltd.
Vita B Complex TabNutrimetics International (Canada) Inc.
Vita-BNutri Dyn Products Ltd.
Vitabanks Vitamin TabVitabank Inc.
Vitachrom GcNikken Usa, Incorporated
Vitaday TabPharmetics (2011) Inc
VitafantLes Laboratoires Vachon Inc.
Vitaflex Dietary SuplementHome Shopping Network Direct
Vitafol CapletEverett Laboratories, Inc.
Vitafol Ob CapletEverett Laboratories, Inc.
Vitafol OneEverett Laboratories, Inc.
Vitafol PlusEverett Laboratories, Inc.
Vitafol UltraEverett Laboratories, Inc.
Vitamin B ComplexMylan Institutional LLC
Vitamin B Complex + C 300mg CapRandle Labs Inc.
Vitamin B Complex + C 600mg TabRandle Labs Inc.
Vitamin B Complex SupplAvacare, Division Of Jeunique International Inc.
Vitamin B Complex TabNutristar Health Products (1987) Inc.
Vitamin B Complex W C 300mg TabLee Adams Laboratories
Vitamin B Compound TabNutrilite, A Division Of Access Business Group, Llc
Vitamin B Compound W C Tab 500mgAdams Labs Ltd.
Vitamin B Compound With Vitamin C Fortis Capsule DtcD.C. Labs Limited
Vitamine 110 LiqFrega Inc.
Vitamines Pour Bebes Et EnfantsHerbes Universelles Inc.
Vp-heme ObVirtus Pharmaceuticals LLC
Salts
Name/CASStructureProperties
Riboflavin 5'-phosphate sodium
6184-17-4
ThumbNot applicableDBSALT000877
Riboflavin 5'-phosphate sodium anhydrous
130-40-5
ThumbNot applicableDBSALT001766
Categories
UNIITLM2976OFR
CAS number83-88-5
WeightAverage: 376.3639
Monoisotopic: 376.138284392
Chemical FormulaC17H20N4O6
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassAlloxazines and isoalloxazines
Direct ParentFlavins
Alternative Parents
Substituents
  • Flavin
  • Quinoxaline
  • Hydroxypyrimidine
  • Pyrimidone
  • Benzenoid
  • Pyrimidine
  • Pyrazine
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Azacycle
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of ariboflavinosis (vitamin B2 deficiency).
PharmacodynamicsRiboflavin 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 actionBinds 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.
Related Articles
AbsorptionVitamin B2 is readily absorbed from the upper gastrointestinal tract.
Volume of distributionNot Available
Protein binding60%
Metabolism

Hepatic.

Route of eliminationNot Available
Half life66-84 minutes
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Riboflavin MetabolismMetabolicSMP00070
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Elixiroral
Tablet (extended-release)oral
Injection, solutionintramuscular; intravenous
Powder for solutionintramuscular; intravenous
Granuleoral
Tabletoral
Syruporal
Liquidintramuscular; intravenous
Powderoral
Dropsoral
Liquidintravenous
Injection, powder, lyophilized, for solutionintravenous
Liquid; tabletoral
Solution/ dropsoral
Powder (effervescent)oral
Liquidoral
Solutionoral
Tablet, chewableoral
Solutionintramuscular; intravenous
Tablet, coatedoral
Solutionintramuscular; intravenous50 mg
Tabletoral10 mg
Tabletoral5 mg
Tabletoral25 mg
Liquid; capsuleoral
Kit
Tablet (extended-release)200 mg
Capsuleoral100 mg
Tablet
Capsuleoral
Capsule, gelatin coatedoral
Capsule, liquid filledoral
Injectionintravenous
Capsule
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point280 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-1.1ALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (11.3 KB)
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-007z000000-86365dedafa031aa7787View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-gcz1000000-ac1b59ab7cc2209f4241View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-hz30000000-72d33eb27b9bd6a13d9eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0mpz000000-874b71fdc78d04853bf0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-00z4000000-a82c54d3153103fcdb1fView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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
ATC CodesA11HA04
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (39.4 KB)
Interactions
Drug Interactions
Drug
PorfimerRiboflavin may increase the photosensitizing activities of Porfimer.
VerteporfinRiboflavin may increase the photosensitizing activities of Verteporfin.
Food InteractionsNot Available

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 (ROS) production. Through its interaction with both TNFRSF1A and CYBA, physically and functionally couples TNFRSF1A to NADPH oxidase. TNF-activation of RFK may enhance the incorporation of FAD in NADPH...
Gene Name:
RFK
Uniprot ID:
Q969G6
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
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). Contributes to heme catabolism and metabolizes linear tetrapyrroles. Can also reduce the complexed Fe(3+) iron to Fe(2+) in the presence of FMN and NADPH. In the liver, converts biliverdin to bilirubin.
Gene Name:
BLVRB
Uniprot ID:
P30043
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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
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
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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 ]
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Drug created on June 13, 2005 07:24 / Updated on April 27, 2016 14:04