U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H20N4O6
Molecular Weight 376.3646
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIBOFLAVIN

SMILES

Cc1cc2c(cc1C)n(C[C@@]([H])([C@@]([H])([C@@]([H])(CO)O)O)O)c3-c(c(nc(=O)n3)O)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 376.3646
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Sources: Journal of Biological Chemistry (1928), 79, 733-8.iez8K9UZvDozY4ZRMmHj4&hl=ru&sa=X&ved=0ahUKEwiJ1reL0b_PAhWJVBQKHbdGBvEQ6AEIQjAF#v=onepage&q=Vitamin%20B2%20was%20discovered%20in%201920s&f=false
Curator's Comment:: https://books.google.ru/books?id=b9ahvNjPFO8C&pg=PA63&lpg=PA63&dq=Vitamin+B2+was+discovered+in+1920s&source=bl&ots=KeZDSvz8CS&sig=gvCH_-

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.46854078E12
Primary
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

1.4684544E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
217.72 nM
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

AUC

ValueDoseCo-administeredAnalytePopulation
674.2 nM × h
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
66 min
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
PubMed

PubMed

TitleDatePubMed
In vivo expression of the collagen-related heat shock protein HSP47, following hyperthermia or photodynamic therapy.
2001
An improved photochemical method for the rapid spectrophotometric detection of superoxide dismutase.
2001
Effect of saturated fatty acid consumption on energy and nutrient intake and blood lipid levels in preschool children.
2001
Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.
2001
Reagentless chemiluminescence flow sensor for the determination of riboflavin in pharmaceutical preparations and human urine.
2001 Aug
Domain structure of riboflavin synthase.
2001 Aug
Effect of photosensitizer riboflavin on the fate of 2,4,6-trinitrotoluene in a freshwater environment.
2001 Aug
Flavin specificity and subunit interaction of Vibrio fischeri general NAD(P)H-flavin oxidoreductase FRG/FRase I.
2001 Aug 1
Photosensitizer initiated attacks on DNA under dry conditions and their inhibition: a DNA archiving issue.
2001 Aug 15
Riboflavin treatment of antiretroviral induced lactic acidosis and hepatic steatosis.
2001 Jul
Spatially focused deposition of capillary electrophoresis effluent onto surface-enhanced Raman-active substrates for off-column spectroscopy.
2001 Jul
Alternative therapies in headache. Is there a role?
2001 Jul
Structures of coenzyme F(420) in Mycobacterium species.
2001 Jul
Thiamine, riboflavin, pyridoxine, and vitamin C status in premature infants receiving parenteral and enteral nutrition.
2001 Jul
Nutritional composition of uncommon foods and their role in meeting micronutrient needs.
2001 Jul
Long-term nutrient intake and early age-related nuclear lens opacities.
2001 Jul
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.
2001 Jul
Riboflavin uptake in human trophoblast-derived BeWo cell monolayers: cellular translocation and regulatory mechanisms.
2001 Jul
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
The effects of thyroxine isomers on free-radical oxidation processes in subcellular fractions of rat cerebral cortex.
2001 Jul-Aug
Efficient pyruvate production by a multi-vitamin auxotroph of Torulopsis glabrata: key role and optimization of vitamin levels.
2001 Jun
Vitamin B intake and status in healthy Havanan men, 2 years after the Cuban neuropathy epidemic.
2001 Jun
Considerations in planning vegan diets: children.
2001 Jun
Effect of UV irradiation on type I collagen fibril formation in neutral collagen solutions.
2001 Jun
[Energy and nutrient intake in compulsory high school students].
2001 Jun
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
Frontal gel chromatographic analysis of the interaction of a protein with self-associating ligands: aberrant saturation in the binding of flavins to bovine serum albumin.
2001 Jun
B vitamins induce an antinociceptive effect in the acetic acid and formaldehyde models of nociception in mice.
2001 Jun 15
The solution structure of the N-terminal domain of riboflavin synthase.
2001 Jun 15
Riboflavin synthesis genes ribE, ribB, ribH, ribA reside in the lux operon of Photobacterium leiognathi.
2001 Jun 15
Light-dependent generation of reactive oxygen species in cell culture media.
2001 Jun 15
Relationships between dietary intake and cognitive function level in Korean elderly people.
2001 Mar
Allergic sensitization and diet: ecological analysis in selected European cities.
2001 Mar
Selenium status in an iodine deficient population of the West Ivory Coast.
2001 Mar
Antioxidant activity of brahma rasayana.
2001 May
Children's nutrient intake at preschool and at home.
2001 May
[Effect of coenzyme Q10 in patients with kidney diseases].
2001 May 24
[Dietary and biochemical riboflavin status in a cohort of young people in the community of Madrid].
2001 May-Jun
Mechanism of the fluorescent light induced suppression of Curly phenotype in Drosophila melanogaster.
2001 Sep
Nutritional assessment in various stages of liver cirrhosis.
2001 Sep
Crystallization and preliminary crystallographic analysis of the recombinant N-terminal domain of riboflavin synthase.
2001 Sep
Nutritional status and dietary intakes of children aged 2-5 years and their caregivers in a rural South African community.
2001 Sep
Metabolic flux analysis with a comprehensive isotopomer model in Bacillus subtilis.
2001 Sep
Stoichiometric growth model for riboflavin-producing Bacillus subtilis.
2001 Sep
A Plackett-Burnam screening design directs the efficient formulation of multicomponent DRV liposomes.
2001 Sep
Validity and reproducibility of a food frequency questionnaire for pregnant Finnish women.
2001 Sep 1
Biosynthesis of the phosphodiester bond in coenzyme F(420) in the methanoarchaea.
2001 Sep 11
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
Riboflavin carrier protein: a serum and tissue marker for breast carcinoma.
2001 Sep 20
The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine.
2001 Sep 6
Patents

Sample Use Guides

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
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 Jun 25 21:11:50 UTC 2021
Edited
by admin
on Fri Jun 25 21:11:50 UTC 2021
Record UNII
TLM2976OFR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIBOFLAVIN
DASH   EP   FCC   HSDB   II   INCI   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INCI   INN  
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
INCI  
INCI  
Official Name English
RIBOFLAVIN [WHO-IP]
Common Name English
RIBOFLAVIN [EP MONOGRAPH]
Common Name English
C.I. FOOD YELLOW 15
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
RIBOFLAVIN [WHO-DD]
Common Name English
E-101(III)
Common Name English
RIBOFLAVIN [USP-RS]
Common Name English
RIBOFLAVIN [INCI]
Common Name English
VITAMIN B2
GREEN BOOK   VANDF  
Common Name English
RIBOFLAVIN [HSDB]
Common Name English
RIBOFLAVIN [FCC]
Common Name English
RIBOFLAVINUM
HPUS   WHO-IP LATIN  
Common Name English
INS NO. 101(I)
Code English
RUSSUPTERIDINE YELLOW III
Common Name English
RIBOFLAVIN [VANDF]
Common Name English
NSC-33298
Code English
RIBOFLAVIN SODIUM PHOSPHATE IMPURITY D [EP]
Common Name English
INS-101(III)
Common Name English
RIBOFLAVIN [USP]
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
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
LIVERTOX 843
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
WHO-ATC A11HA04
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
JECFA EVALUATION INS-101(III)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
LOINC 6695-1
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
DSLD 2543 (Number of products:6659)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
LOINC 27099-1
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 27
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
LOINC 49038-3
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
NCI_THESAURUS C45812
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
FDA ORPHAN DRUG 352511
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
FDA ORPHAN DRUG 344911
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
LOINC 18374-9
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
LOINC 2924-9
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
DSLD 203 (Number of products:536)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-101(I)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
FDA ORPHAN DRUG 468414
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
WHO-ATC S01XA26
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
CFR 21 CFR 184.1695
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-101(III)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
LOINC 73723-9
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
Code System Code Type Description
HSDB
817
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
PUBCHEM
493570
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
JECFA EVALUATION
INS-101(I)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
RIBOFLAVIN
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY Description: A yellow to orange-yellow, crystalline powder; odourless or almost odourless. Solubility: Very slightly soluble in water; practically insoluble in ethanol (~750 g/l) TS, ether R, and acetone R. Category: Vitamin. Storage: Riboflavin should be kept in a tightly closed container, protected from light. Additional information: Riboflavin has a bitter taste. Solutions of Riboflavin, especially in dilute solutions of alkalis, deterioraterapidly when exposed to light. Definition: Riboflavin contains not less than 98.0% and not more than 102.0% of C17H20N4O6, calculated with reference to the dried substance.
EPA CompTox
83-88-5
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
FDA UNII
TLM2976OFR
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
NCI_THESAURUS
C808
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-507-1
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
MESH
D012256
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL1534
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
EVMPD
SUB10298MIG
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-101(I)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
INN
419
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
WIKIPEDIA
RIBOFLAVIN
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
MERCK INDEX
M9595
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
2834
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
CAS
83-88-5
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
USP_CATALOG
1603006
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY USP-RS
RXCUI
9346
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB00140
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
JECFA MONOGRAPH
INS-101(III)
Created by admin on Fri Jun 25 21:11:50 UTC 2021 , Edited by admin on Fri Jun 25 21:11:50 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurity by the corresponding correction factor: impurity C = 2.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurity by the corresponding correction factor: impurity B = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurity by the corresponding correction factor: impurity A = 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
IMPURITY -> PARENT
correction factors: for the calculation of content, multiply the peak areas of the following impurity by the corresponding correction factor: impurity D = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Related Record Type Details
ACTIVE MOIETY