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Identification
NameRiboflavin
Accession NumberDB00140  (APRD00626, EXPT02760, NUTR00010)
TypeSmall Molecule
GroupsApproved, Nutraceutical
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)benzo[g]pteridine-2,4(3H,10H)-dione
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazine
7,8-Dimethyl-10-ribitylisoalloxazine
e101
Lactoflavin
Lactoflavine
Riboflavin
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 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vit B2 Ctr Srt 200mgtablet (extended-release)200 mgBioenergy Inc.1979-12-311998-06-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Acti-ribo/ribo 5-phosph Caplettablet100 mgoralActi Form Ltd.1991-12-312005-03-21Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
B-2 Caps 100mgcapsule100 mgoralTwin Laboratories Inc.1995-12-311999-11-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
B2 Tab 100mgtablet100 mgoralVita Health Products Inc1979-12-312002-07-31Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Riboflavin 5 Phosphate Cap 50mgcapsule50 mgoralThorne Research Canada Ltd.1985-12-312001-07-13Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Riboflavin Tab 10mgtablet10 mgoralSwiss Herbal Remedies Ltd.1971-12-311999-09-09Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Riboflavin Tab 5mgtablet5 mgoralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1957-12-312002-07-31Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Riboflavin-S Tab 25mgtablet25 mgoralNutri West Products Ltd.1993-12-311997-08-05Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vita-flavine Cap 100mgcapsule100 mgoralLes Laboratoires Vachon Inc.1991-12-312001-08-07Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B-2capsule100 mgoralSisu Inc.2001-09-012006-07-31Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B-2 50 Mg Tabletstablet50 mgoralGeneral Nutrition Canada Inc.1997-04-182006-08-03Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B-2 Riboflavin 100mg Capsulescapsule100 mgoralAlbi Naturals1999-04-302009-07-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B2 100 mgcapsule100 mgoralFlora Manufacturing And Distributing Ltd.2002-03-152004-08-04Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B2 100mgtablet100 mgoralGreat Earth Companies, Inc.1998-08-252002-10-02Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B2 Tab 100mgtablet100 mgoralQuest Vitamins A Div Of Purity Life Health Products1978-12-312001-07-06Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B2 Tab 4mg USP Chewabletablet4 mgoralLab Gernetic Int Ltee1985-12-311997-02-21Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Vitamin B2 Tablets 100mgtablet100 mgoralNu Life Nutrition Ltd.1987-12-312005-03-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
International Brands
NameCompany
BisulaseNot Available
Brand mixtures
NameLabellerIngredients
AntlervironClassical Remedia Ltd
Avon Nutrivance Stress FormulaAvon Canada Ulc
B 6 PlusAnabolic Laboratories Inc.
B Complex TabletsGolden Neo Life Diamite International, Limited
B Complex W Vit C W Non-med Yeast&liver TabPharmavite Llc
B Complex With C 300mg TabPharmavite Llc
B Plus C 300mg Timed ReleaseVita Health Products Inc
B Stress C + Iron & ViteStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
B With C 500 CapPharmetics (2011) Inc
B-2 100mg With C 20mgGahler Enterprises Ltd.
B-50 Complex TabVita Health Products Inc
B-complex TabletsShaklee Canada Inc
B-plexLand Art Inc.
B50 B Complex TabNutristar Health Products (1987) Inc.
B6 Plus TabVita Health Products Inc
Balanced B-100 B-complex Vitamins TabPharmavite Llc
Balanced B-100 Timed ReleasePharmavite Llc
Balanced B-50 ComplexLeiner Health Products Inc.
Balanced B-complex Vit + Vit C&e TabPharmavite Llc
Beminal 500 TabsWyeth Canada
Beminal With C Fortis PwsWyeth Ayerst Canada Inc.
Bio-fenLisa & Gerry Freundl
BiovitaIldong Pharmaceutical Co., Ltd.
C-B ComplexAvacare, Division Of Jeunique International Inc.
C.R.T. X Multivitamin & Mineral Powder MixMetaform Ltd.
Carbassist TabletsWyeth Consumer Healthcare Inc.
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.
Centrum Junior (chewable)Whitehall Robins Inc.
Centrum Junior Regular (chewable Tablets)Whitehall Robins Inc.
Chela Potassium PlusNu Life Nutrition Ltd.
Chewable Children's Complete Multivitamins With Essential MineralsWn Pharmaceuticals Ltd.
Chewable MultivitaminsWn Pharmaceuticals Ltd.
Chewable Multivitamins Plus IronWn Pharmaceuticals Ltd.
Chewable Multivitamins With Extra CWn Pharmaceuticals Ltd.
Children Choice Multivit Chewable TabSwiss Herbal Remedies Ltd.
Children's Chewable Multi-vitaminWn Pharmaceuticals Ltd.
Children's Chewable Multi-vitamin Complete With MineralsWn Pharmaceuticals Ltd.
Children's Chewable Multiple VitaminsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Children's Chewable Multivitamins With MineralsWn Pharmaceuticals Ltd.
Children's Vitamins ChewableVita Health Products Inc
Childrens Chewable Multiple Vitamins TabPharmavite Llc
Citranatal DHAMission Pharmacal Company
Citranatal RxMission Pharmacal Company
Complex 5 - PwrAst Research
Complex-75Frega Inc.
Complexe B-75Frega Inc.
Concept DHAUs Pharmaceutical Corporation
Concept ObUs Pharmaceutical Corporation
D'pantothenic Acid-B1-B2 TabHealth Thru Herbs Inc.
Daily Energy Brand B-complexEnzymatic Therapy (Canada) Inc.
Dia-viteR & D Laboratories Inc.
DiaplexNephro Tech, Inc.
Ez-flexMetagenics, Inc.
Feminique W Iron and Calcium TabStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Ferra Naka Plus VitaminsNaka Sales Ltd.
Floradix Formula LiqFlora Manufacturing And Distributing Ltd.
Floravit - SyrFlora Manufacturing And Distributing Ltd.
Folcaps Care OneMidlothian Laboratories
For Kids Only Chewable MultivitaminsStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Formula CnBalance Plus, Inc.
Formula D.S.Golden Pride International
Formula Fm Vitamins & Minerals TabMetagenics, Inc.
Formula Sf-710Thorne Research Inc.
Geritol LiquidGlaxosmithkline Consumer Healthcare Inc.
Hemarexin AmpLab Bio Chimique Inc.,Division Of Technilab Pharma Inc.
Hemenatal ObWh Nutritionals, Llc
Hi Potency Balanced B-100 Complex - TabLeiner Health Products Inc.
Hill.viteHillestad Pharmaceuticals Usa
Homosistrol CapsulesMacromed Pharmicia Inc.
Homosistrox CapsulesS.A.F. Nutritional Products Inc.
Integra PlusUs Pharmaceutical Corporation
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.
Junior Multi Vitamins - RegularVita Health Products Inc
Kanga Sport Vitamins B & C Plus MineralsLacombe Drugs (1992) Ltd
Kanga-B Vitamin B Group + CLacombe Drugs (1992) Ltd
Kanga-kid Multi-vitamin & MineralLacombe Drugs (1992) Ltd
Kid's Choice Children's Chewable Vitamins - TabVita Health Products Inc
Kids Stuff TabletsVita Health Products Inc
Kids Stuff With Iron TabletsVita Health Products Inc
Kimchi Vitamin Chewable MultivitaminTobico
Leritone JuniorInstitut De Recherche Biologique Yves Ponroy Canada Inc.
Livron Plus AmpouleMedic Laboratory LtÉe
Maxi 6 LiqDesbergers LtÉe, Division Of Technilab Inc.
Megavites TabIcn Canada Ltd.
Multi #2W 7 Clay Inc.
Multi Vitamin & MineralsWn Pharmaceuticals Ltd.
Multi Vitamin Plus IronWn Pharmaceuticals Ltd.
Multi-min Electro C Pow Plus B2Quest Vitamins A Div Of Purity Life Health Products
Multi-vitaminLLC Federal Solutions
Multi-vitamin Fluoride and Iron DropsBoca Pharmacal, LLC
Multi-vitamin Fluoride DropsH.J. Harkins Company, Inc.
Multi-vitamin With FluorideGolden State Medical Supply, Inc.
Multi-vitaminsWn Pharmaceuticals Ltd.
Multi-vitamins for Infusion LiqDavid Bull Laboratories (Pty) Ltd.
Multiple VitaminsGfr Pharma Ltd.
Multivit-liqPharmalab Inc.
MultivitaminLaboratoires Confab Inc
Multivitamines Plus C Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamines Plus Fer Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamines Pour Enfants (chewable Tablets)Laboratoire Lalco Inc.
Multivitamins for ChildrenQuest Vitamins A Div Of Purity Life Health Products
MvcSancilio & Company Inc
Mvc-fluorideSancilio & Company Inc.
Mynephrocaps Dialysis/stress Vitamin SupplementMartin Ekwealor Pharmaceuticals, Inc.
Nata KompleteWh Nutritionals, Llc
Neo Bex ElixirNeolab Inc
Neo-bexNeolab Inc
Neo-vites & Minerals TabNeolab Inc
NephrocapsCardinal Health
Nutrol-B-complexRolmex International Inc.
O-cal Prenatal VitaminPharmics, Inc.
Phosthenine Vitamines Et Fer (ampoules Buvable)Laboratoires Cortunon Inc.
Polymine Avec Zinc Et CuivreLes Laboratoires Vachon Inc.
Prefera Ob Plus DHAAlaven Pharmaceutical LLC
PreferaobMEDA Pharmaceuticals
Preferaob Plus DHAAlaven Pharmaceutical LLC
Prenatal Mega AntioxidantUsana Health Services, Inc.
Prenatal Vitamins Plusbryant ranch prepack
Prenate StarAvion Pharmaceuticals, Llc
Prevital TabBio Vita
Purevit Dualfe PlusPure Tek Corporation
Reaphirm Plant Source DHAEverett Laboratories, Inc.
Reno CapsNnodum Pharmaceuticals
ReplaviteStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Se-tan PlusSeton Pharmaceuticals
Somarexin and C 1000Laboratoire Lalco Inc.
Stress B Complex With C, E & IronPharmavite Llc
Stress Complex 600 Avec Vit E Cuivre ZincFrega Inc.
Stress FormulaVita Health Products Inc
Stress Formula + IronVita Health Products Inc
Stress Formula Multivitamin Tablets USPLeiner Health Products Inc.
Stress Formula TabNature's Sunshine Products Of Canada Ltd.
Stress Tab With Iron and Vitamin EVita Health Products Inc
Stress Tab With Zinc, Copper and Vitamin EVita Health Products Inc
Stressease Plus Vitamins and MineralsJamieson Laboratories Ltd
Strovite Forte CapletEverett Laboratories, Inc.
Strovite One CapletsEverett Laboratories, Inc.
Super PantoplexNu Life Nutrition Ltd.
Super Vitalex Ampoule BuvableCarmaran LtÉe
Supravite 10ml AmpouleNobel Pharm Enr.
Supravite Bouteille 250mlNobel Pharm Enr.
Supravite C 1000Nobel Pharm Enr.
Supravite Stress Avec Vit EPharmalab Inc.
Supravite Stress Avec Vit E Cuivre Et ZincPharmalab Inc.
Supravite Stress Avec Vit E Et FerPharmalab Inc.
Swical-energy-2Les Laboratoires Swisse Inc.
T.R.I. B-plex SrcAnabolic Laboratories Inc.
Tandem ObUs Pharmaceutical Corporation
Tandem PlusUs Pharmaceutical Corporation
Tender Age Multi VitaminsJamieson Laboratories Ltd
Toni Com LiqVitalab
Ultra EnerforceNutribon (1986) Inc.
V-natalVirtus Pharmaceuticals
Vigo Multivitamins Drops/lozengeAshbury Research Corporation
Virt-bal DHA PlusVirtus Pharmaceuticals
Virt-capsVirtus Pharmaceuticals LLC
Virt-PNVirtus Pharmaceuticals
Virt-vite PlusVirtus Pharmaceuticals LLC
Vita-B-75 CapLes Laboratoires Vachon Inc.
Vitabanks Vitamin TabVitabank Inc.
Vitafer - LiqFrega Inc.
Vitafol CapletEverett Laboratories, Inc.
Vitafol Ob CapletEverett Laboratories, Inc.
Vitafol OneEverett Laboratories, Inc.
Vitafol PlusEverett Laboratories, Inc.
Vitamin B Complex Plus C 300mg Timed ReleaseVita Health Products Inc
Vitamin B Complex TabNutristar Health Products (1987) Inc.
Vitamin B Compound TabNutrilite, A Division Of Access Business Group, Llc
Vitamine Du Groupe B Plus Fer - LiqPharmalab Inc.
Vitamines Pour Bebes Et EnfantsHerbes Universelles Inc.
Vitogen B Compound W C Fortis CapsulesStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Vitogen B Stress C Vit E Zinc & CopStanley Pharmaceuticals, A Division Of Vita Health Products Inc.
Vp-heme ObVirtus Pharmaceuticals LLC
Salts
Name/CASStructureProperties
Riboflavin phosphate sodium dihydrate
ThumbNot applicableDBSALT000877
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[C@H](O)[C@H](O)[C@H](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.
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
PathwaysNot Available
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
Tabletoral100 mg
Tablet (extended-release)oral
Powder for solutionintravenous
Granuleoral
Tabletoral
Powderoral
Syruporal
Tablet (effervescent)oral
Powder (effervescent)oral
Liquidoral
Solutionoral
Liquidintravenous
Tablet, chewableoral
Elixiroral
Tablet, coatedoral
Capsuleoral50 mg
Solutionintramuscular; intravenous50 mg
Tabletoral10 mg
Tabletoral5 mg
Tabletoral25 mg
Liquid; tabletoral
Capsule (sustained-release)oral
Lozengeoral
Kit
Tablet (extended-release)200 mg
Capsuleoral100 mg
Tablet
Capsuleoral
Capsule, gelatin coatedoral
Capsule, liquid filledoral
Tabletoral50 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
External Links
ATC CodesNot Available
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

1. Riboflavin kinase

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: ligand

Components

Name UniProt ID Details
Riboflavin kinase Q969G6 Details

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
  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
  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. 2006 Sep-Oct;78(5):63-9. Pubmed
  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
  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
  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. Pubmed

2. Riboflavin synthase

Kind: Protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: other

Components

Name UniProt ID Details
Riboflavin synthase P0AFU8 Details

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. Pubmed
  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. Epub 2010 Feb 8. Pubmed

3. Flavin reductase (NADPH)

Kind: Protein

Organism: Human

Pharmacological action: yes

Actions: product of

Components

Name UniProt ID Details
Flavin reductase (NADPH) P30043 Details

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
  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

Enzymes

1. Amine oxidase [flavin-containing] A

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: cofactor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

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

2. Methylenetetrahydrofolate reductase

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: cofactor

Components

Name UniProt ID Details
Methylenetetrahydrofolate reductase P42898 Details

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
  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

Transporters

1. Solute carrier family 22 member 6

Kind: Protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08