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

Molecular Formula	C17H20N4O6
Molecular Weight	376.3639
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis].	2001	11355481
Effects of vitamins on hepatic nuclear binding of L-tryptophan.	2001	11332447
Determination of riboflavin, flavin mononucletide and flavin adenine dinucleotide in biological tissues by capillary zone electrophoresis and laser-induced fluorescence detection.	2001 Apr	11358143
Adverse effects of oral naltrexone: analysis of data from two clinical trials.	2001 Apr	11349393
Possible cause of G-C-->C-G transversion mutation by guanine oxidation product, imidazolone.	2001 Apr	11325592
Natural therapies for ocular disorders, part two: cataracts and glaucoma.	2001 Apr	11302779
Biosynthesis of riboflavin. The reaction catalyzed by 6,7-dimethyl-8-ribityllumazine synthase can proceed without enzymatic catalysis under physiological conditions.	2001 Apr 20	11304170
Reagentless chemiluminescence flow sensor for the determination of riboflavin in pharmaceutical preparations and human urine.	2001 Aug	11534612
Flavin specificity and subunit interaction of Vibrio fischeri general NAD(P)H-flavin oxidoreductase FRG/FRase I.	2001 Aug 1	11469801
Certification of B-group vitamins (B1, B2, B6, and B12) in four food reference materials.	2001 Jan	11305253
Riboflavin treatment of antiretroviral induced lactic acidosis and hepatic steatosis.	2001 Jul	11508132
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
Synergistic interactions of multiple mutations on catalysis during the hydroxylation reaction of p-hydroxybenzoate hydroxylase: studies of the Lys297Met, Asn300Asp, and Tyr385Phe mutants reconstituted with 8-Cl-flavin.	2001 Jul 31	11467930
The effects of thyroxine isomers on free-radical oxidation processes in subcellular fractions of rat cerebral cortex.	2001 Jul-Aug	11508500
Efficient pyruvate production by a multi-vitamin auxotroph of Torulopsis glabrata: key role and optimization of vitamin levels.	2001 Jun	11525614
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
Biosynthesis of riboflavin: studies on the mechanism of GTP cyclohydrolase II.	2001 Jun 22	11301327
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
Hexavalent chromium stimulation of riboflavin synthesis in flavinogenic yeast.	2001 Mar	11368272
Steady-state and time-resolved spectroscopy of F420 extracted from methanogen cells and its utility as a marker for fecal contamination.	2001 Mar	11312822
Antioxidant activity of brahma rasayana.	2001 May	11510128
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
Crystal structure of riboflavin synthase.	2001 May 9	11377200
Mechanism of the fluorescent light induced suppression of Curly phenotype in Drosophila melanogaster.	2001 Sep	11536279
Nutritional assessment in various stages of liver cirrhosis.	2001 Sep	11527674
Crystallization and preliminary crystallographic analysis of the recombinant N-terminal domain of riboflavin synthase.	2001 Sep	11526324
Nutritional status and dietary intakes of children aged 2-5 years and their caregivers in a rural South African community.	2001 Sep	11517732
Metabolic flux analysis with a comprehensive isotopomer model in Bacillus subtilis.	2001 Sep	11505384
A Plackett-Burnam screening design directs the efficient formulation of multicomponent DRV liposomes.	2001 Sep	11470202
Validity and reproducibility of a food frequency questionnaire for pregnant Finnish women.	2001 Sep 1	11532789
Biosynthesis of the phosphodiester bond in coenzyme F(420) in the methanoarchaea.	2001 Sep 11	11535063
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
The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine.	2001 Sep 6	11529760

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:49 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:49 GMT 2023`
Record UNII	TLM2976OFR
Record Status	`Validated (UNII)`
Record Version

Download

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