RIBOFLAVIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H20N4O6
Molecular Weight	376.3639
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)NC(=O)C3=N2

InChI

InChIKey=AUNGANRZJHBGPY-SCRDCRAPSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/203324s000lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22406738

Riboflavin (vitamin B2) is part of the vitamin B group. Riboflavin 5’-phosphate is the precursor of two coenzymes, flavin adenine dinucleotide and flavin mononucleotide, which catalyze oxidation/reduction reactions involved in a number of metabolic pathways. FAD and riboflavin phosphate in foods are hydrolyzed in the intestinal lumen by nucleotide diphosphatase and a variety of nonspecific phosphatases to yield free riboflavin, which is absorbed in the upper small intestines by a sodium-dependent saturable mechanism. Riboflavin has been used in several clinical and therapeutic situations. For over 30 years, riboflavin supplements have been used as part of the phototherapy treatment of neonatal jaundice. Corneal ectasia is a progressive thinning of the cornea; the most common form of this condition is keratoconus. Collagen cross-linking is a non-surgical treatment intended to slow progression of corneal ectasia by strengthening corneal tissue. The standard protocol calls for application directly to the eye of a 0.1% riboflavin solution for 30 minutes followed by 30 minutes of ultraviolet-A irradiation with a wavelength of 370 nm and power of 3 mW/cm2. Under the conditions used for corneal collagen cross-linking, riboflavin 5‘-phosphate functions as a photo enhancer and generates singlet oxygen which is responsible for the cross-linking.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Progressive keratoconus 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/203324s000lbl.pdf	Primary		Approved 8429	PHOTREXA Approved Use PHOTREXA® VISCOUS and PHOTREXA® are indicated for use in corneal collagen cross-linking in combination with the KXL™ System for the treatment of 1.1 Progressive keratoconus 1.2 Corneal ectasia following refractive surgery. Launch Date 2016
Corneal ectasia 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/203324s000lbl.pdf	Primary		Approved 8429	PHOTREXA Approved Use PHOTREXA® VISCOUS and PHOTREXA® are indicated for use in corneal collagen cross-linking in combination with the KXL™ System for the treatment of 1.1 Progressive keratoconus 1.2 Corneal ectasia following refractive surgery. Launch Date 2016

C_max

Value	Dose	Co-administered	Analyte	Population
217.72 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8604671	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		RIBOFLAVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
674.2 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/8604671	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		RIBOFLAVIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
66 min OTHER GOV https://www.glowm.com/resources/glowm/cd/pages/drugs/qr016.html	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		RIBOFLAVIN unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17015	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17015
ChemicalBook	CB4383318	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4383318
MolPort	MolPort-003-934-329	https://www.molport.com/shop/molecule-link/MolPort-003-934-329
Selleck Chemicals	Riboflavin-Vitamin-B2	http://www.selleckchem.com/products/Riboflavin-Vitamin-B2.html
ZINC	ZINC000002036848	http://zinc15.docking.org/substances/ZINC000002036848
eMolecules	711592	https://www.emolecules.com/cgi-bin/more?vid=711592

PubMed

Title	Date	PubMed
In vivo expression of the collagen-related heat shock protein HSP47, following hyperthermia or photodynamic therapy.	2001	11482817
An improved photochemical method for the rapid spectrophotometric detection of superoxide dismutase.	2001	11450983
Effect of saturated fatty acid consumption on energy and nutrient intake and blood lipid levels in preschool children.	2001	11423704
Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.	2001	11423008
[Effects of biologically active supplements on the antioxidant and vitamin status of patients with hypertension and ischemic heart disease].	2001	11338339
Effects of vitamins on hepatic nuclear binding of L-tryptophan.	2001	11332447
Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human.	2001	11244182
The stressed synovium.	2001	11178114
Biosynthesis of the methanogenic cofactors.	2001	11153270
Adverse effects of oral naltrexone: analysis of data from two clinical trials.	2001 Apr	11349393
The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid.	2001 Apr	11345651
Serum levels assessment of vitamin A, E, C, B2 and carotenoids in malnourished and non-malnourished hospitalized elderly patients.	2001 Apr	11327745
Riboflavin synthase of Escherichia coli. Effect of single amino acid substitutions on reaction rate and ligand binding properties.	2001 Apr 13	11278450
Effect of photosensitizer riboflavin on the fate of 2,4,6-trinitrotoluene in a freshwater environment.	2001 Aug	11482649
Flavin specificity and subunit interaction of Vibrio fischeri general NAD(P)H-flavin oxidoreductase FRG/FRase I.	2001 Aug 1	11469801
Photosensitizer initiated attacks on DNA under dry conditions and their inhibition: a DNA archiving issue.	2001 Aug 15	11485843
Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli.	2001 Feb 6	11170472
An unusual photohaemolytic property of riboflavin.	2001 Jan	11259847
Nutritional evaluation of some processed catering foods.	2001 Jan	11225180
Manothermosonication of foods and food-resembling systems: effect on nutrient content and nonenzymatic browning.	2001 Jan	11170615
Crystal structure of 3,4-dihydroxy-2-butanone 4-phosphate synthase of riboflavin biosynthesis.	2001 Jan 10	11342130
Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage.	2001 Jan 25	11152968
Thiamine, riboflavin, pyridoxine, and vitamin C status in premature infants receiving parenteral and enteral nutrition.	2001 Jul	11479410
Nutritional composition of uncommon foods and their role in meeting micronutrient needs.	2001 Jul	11474897
Long-term nutrient intake and early age-related nuclear lens opacities.	2001 Jul	11448323
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
Riboflavin uptake in human trophoblast-derived BeWo cell monolayers: cellular translocation and regulatory mechanisms.	2001 Jul	11408551
Vitamin B intake and status in healthy Havanan men, 2 years after the Cuban neuropathy epidemic.	2001 Jun	11430779
Considerations in planning vegan diets: children.	2001 Jun	11424545
Effect of UV irradiation on type I collagen fibril formation in neutral collagen solutions.	2001 Jun	11419538
[Energy and nutrient intake in compulsory high school students].	2001 Jun	11412401
Diet quality, nutrient intake, weight status, and feeding environments of girls meeting or exceeding recommendations for total dietary fat of the American Academy of Pediatrics.	2001 Jun	11389293
19F NMR ligand perturbation studies on 6,7-bis(trifluoromethyl)-8-ribityllumazine-7-hydrates and the lumazine synthase complex of Bacillus subtilis. Site-directed mutagenesis changes the mechanism and the stereoselectivity of the catalyzed haloform-type reaction.	2001 Jun 1	11375002
The solution structure of the N-terminal domain of riboflavin synthase.	2001 Jun 15	11399071
Riboflavin synthesis genes ribE, ribB, ribH, ribA reside in the lux operon of Photobacterium leiognathi.	2001 Jun 15	11396941
Light-dependent generation of reactive oxygen species in cell culture media.	2001 Jun 15	11390187
Relationships between dietary intake and cognitive function level in Korean elderly people.	2001 Mar	11406779
Allergic sensitization and diet: ecological analysis in selected European cities.	2001 Mar	11405517
Selenium status in an iodine deficient population of the West Ivory Coast.	2001 Mar	11385942
Hexavalent chromium stimulation of riboflavin synthesis in flavinogenic yeast.	2001 Mar	11368272
Limiting light-induced lipid peroxidation and vitamin loss in infant parenteral nutrition by adding multivitamin preparations to Intralipid.	2001 Mar	11332161
Assessment of gastric acidity of Japanese subjects over the last 15 years.	2001 Mar	11256493
Characterization of chicken riboflavin carrier protein gene structure and promoter regulation by estrogen.	2001 Mar	11255512
Direct voltammetry for vitamin B(2) determination in aqueous solution by using glassy carbon electrode.	2001 Mar	11248517
Children's nutrient intake at preschool and at home.	2001 May	11430705
Potential for creatine and other therapies targeting cellular energy dysfunction in neurological disorders.	2001 May	11357946
[Effect of coenzyme Q10 in patients with kidney diseases].	2001 May 24	11411060
Mechanism of the fluorescent light induced suppression of Curly phenotype in Drosophila melanogaster.	2001 Sep	11536279
Stoichiometric growth model for riboflavin-producing Bacillus subtilis.	2001 Sep	11505383
Helix stabilization in the C-terminal peptide of chicken riboflavin carrier protein enhances immunogenicity and prolongs contraceptive potential as an epitope-based vaccine in female rats.	2001 Sep 14	11549280

Patents

Sample Use Guides

In Vivo Use Guide

instill 1 drop topically on the eye every 2 minutes for 30 minutes. After 30 minutes, examine the eye under slit lamp for presence of a yellow flare in the anterior chamber. If flare is not detected, instill 1 drop every 2 minutes for an additional 2 to 3 drops and recheck for yellow flare. Once flare is observed, perform ultrasound pachymetry. If corneal thickness is less than 400 microns, instill 2 drops every 5 to 10 seconds until the corneal thickness increases to at least 400 microns.

Route of Administration: Other

In Vitro Use Guide

Corneal stromal cells were covered with collagen (200 µL or 500 µL) and 0.1% riboflavin, and then exposed to ultraviolet light at 370 nm for 30 minutes

Name

Type

Language

RIBOFLAVIN

Official Name

English

LACTO-FLAVIN

Common Name

English

Riboflavine

Common Name

English

RIBOFLAVIN [ORANGE BOOK]

Common Name

English

RIBOFLAVIN [II]

Common Name

English

RIBOFLAVIN [MART.]

Common Name

English

LACTOFLAVIN

Official Name

English

RIBOFLAVIN [WHO-IP]

Common Name

English

RIBOFLAVIN [EP MONOGRAPH]

Common Name

English

C.I. FOOD YELLOW 15

Common Name

English

RIBOFLAVIN SODIUM PHOSPHATE IMPURITY D [EP IMPURITY]

Common Name

English

NCI-0033298

Code

English

RIBOFLAVIN [JAN]

Common Name

English

VITAMIN B2 [GREEN BOOK]

Common Name

English

7,8-DIMETHYL-10-(1'-D-RIBITYL)ISOALLOXAZINE

Common Name

English

RIBOFLAVIN [MI]

Common Name

English

VITAMIN B-2

Common Name

English

INS NO.101(III)

Common Name

English

VITAMIN B2 [VANDF]

Common Name

English

LACTOFLAVIN [INCI]

Common Name

English

VITAMIN B2 (AS RIBOFLAVIN)

Common Name

English

BISULASE

Brand Name

English

RIBOFLAVINUM [WHO-IP LATIN]

Common Name

English

VITAMIN-B2

Common Name

English

E-101(III)

Common Name

English

RIBOFLAVIN [USP-RS]

Common Name

English

RIBOFLAVIN [INCI]

Common Name

English

VITAMIN B2

Common Name

English

RIBOFLAVIN [HSDB]

Common Name

English

RIBOFLAVIN [FCC]

Common Name

English

RIBOFLAVINUM

Common Name

English

INS NO. 101(I)

Code

English

RUSSUPTERIDINE YELLOW III

Common Name

English

RIBOFLAVIN [VANDF]

Common Name

English

RIBOFLAVIN [USP MONOGRAPH]

Common Name

English

NSC-33298

Code

English

INS-101(III)

Common Name

English

Riboflavin [WHO-DD]

Common Name

English

riboflavin [INN]

Common Name

English

RIBOFLAVINUM [HPUS]

Common Name

English

C.I. 50900

Common Name

English

Classification Tree Code System Code

WHO-VATC

QA11HA04