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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
SynonymLanguageCode
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)pentitolNot AvailableNot Available
6,7-Dimethyl-9-D-ribitylisoalloxazineNot AvailableNot Available
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)benzo[g]pteridine-2,4(3H,10H)-dioneNot AvailableNot Available
7,8-Dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)isoalloxazineNot AvailableNot Available
7,8-Dimethyl-10-ribitylisoalloxazineNot AvailableNot Available
e101Not AvailableNot Available
LactoflavinNot AvailableNot Available
LactoflavineNot AvailableNot Available
RiboflavinNot AvailableNot Available
RiboflavinaSpanishINN
RiboflavineFrenchINN
RiboflavinumLatinINN
Vitamin B2Not AvailableNot Available
Vitamin GNot AvailableNot Available
Salts
Name/CAS Structure Properties
Riboflavin phosphate sodium dihydrate
Thumb Not applicable DBSALT000877
Brand names
NameCompany
BisulaseNot Available
Brand mixturesNot Available
Categories
CAS number83-88-5
WeightAverage: 376.3639
Monoisotopic: 376.138284392
Chemical FormulaC17H20N4O6
InChI KeyAUNGANRZJHBGPY-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
Mass Specshow(11.3 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPteridines and Derivatives
SubclassAlloxazines and Isoalloxazines
Direct parentFlavins
Alternative parentsPentoses; Quinoxalines; Toluenes; Pyrimidones; Pyrazines; 1,2-Diols; Secondary Alcohols; Polyamines; Primary Alcohols
Substituentsquinoxaline; pentose monosaccharide; pyrimidone; toluene; benzene; pyrazine; monosaccharide; pyrimidine; saccharide; secondary alcohol; polyol; 1,2-diol; primary alcohol; polyamine; alcohol; amine; organonitrogen compound
Classification descriptionThis compound belongs to the flavins. These are compounds containing a flavin (7,8-dimethyl-benzo[g]pteridine-2,4-dione) moiety, whose structure is characterized by an isoalloaxzine tricyclic ring.
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
Pathways
PathwayCategorySMPDB ID
Riboflavin MetabolismMetabolicSMP00070
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9516
CYP450 2C19 substrate Inhibitor 0.7302
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Riboflavin powder0.44USDg
Riboflavin 100 mg tablet0.09USDtablet
Riboflavin 50 mg tablet0.08USDtablet
Vitamin b-2 50 mg tablet0.08USDtablet
Ribo 100 mg tablet0.04USDtablet
Vitamin b-2 25 mg tablet0.02USDtablet
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 solubility6.57e-01 g/lALOGPS
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 area155.05ChemAxon
rotatable bond count5ChemAxon
refractivity96.27ChemAxon
polarizability37.5ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Hansgeorg Ernst, Wolfram Schmidt, Joachim Paust, “Preparation of riboflavin.” U.S. Patent US4567261, issued August, 1958.

US4567261
General Reference
  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
ResourceLink
KEGG DrugD00050
KEGG CompoundC00255
PubChem Compound493570
PubChem Substance46507342
ChemSpider6501
ChEBI17015
ChEMBLCHEMBL1534
PharmGKBPA451242
Drug Product Database2239929
Drugs.comhttp://www.drugs.com/mtm/riboflavin.html
PDRhealthhttp://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/rib_0263.shtml
WikipediaRiboflavin
ATC CodesA11HA04
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(39.4 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
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