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

Details

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

SHOW SMILES / InChI
Structure of RIBOFLAVIN

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
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

2016
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

2016
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
Elevation of serum riboflavin carrier protein in breast cancer.
1999 Nov
Effects of vitamins on hepatic nuclear binding of L-tryptophan.
2001
Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human.
2001
Biosynthesis of riboflavin.
2001
Adverse effects of oral naltrexone: analysis of data from two clinical trials.
2001 Apr
Nutritional evaluation of ethanol-extracted lentil flours.
2001 Apr
Riboflavin synthase of Escherichia coli. Effect of single amino acid substitutions on reaction rate and ligand binding properties.
2001 Apr 13
Evaluation of the hydrogen bonding interactions and their effects on the oxidation-reduction potentials for the riboflavin complex of the Desulfovibrio vulgaris flavodoxin.
2001 Apr 2
Biosynthesis of riboflavin. The reaction catalyzed by 6,7-dimethyl-8-ribityllumazine synthase can proceed without enzymatic catalysis under physiological conditions.
2001 Apr 20
Domain structure of riboflavin synthase.
2001 Aug
Flavin specificity and subunit interaction of Vibrio fischeri general NAD(P)H-flavin oxidoreductase FRG/FRase I.
2001 Aug 1
Studies on reactions of oxidizing sulfur-sulfur three-electron-bond complexes and reducing alpha-amino radicals derived from OH reaction with methionine in aqueous solution.
2001 Feb 16
Characterization of the FAD-containing N-methyltryptophan oxidase from Escherichia coli.
2001 Feb 6
Certification of B-group vitamins (B1, B2, B6, and B12) in four food reference materials.
2001 Jan
Nutritional evaluation of some processed catering foods.
2001 Jan
Porcine Choroid plexus epithelial cells in culture: regulation of barrier properties and transport processes.
2001 Jan 1
Crystal structure of 3,4-dihydroxy-2-butanone 4-phosphate synthase of riboflavin biosynthesis.
2001 Jan 10
Novel pH-sensitive citrate cross-linked chitosan film for drug controlled release.
2001 Jan 5
Marginal vitamin and mineral intake of Costa Rican adolescents.
2001 Jan-Feb
Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae).
2001 Jan-Feb
Structures of coenzyme F(420) in Mycobacterium species.
2001 Jul
The effects of thyroxine isomers on free-radical oxidation processes in subcellular fractions of rat cerebral cortex.
2001 Jul-Aug
Considerations in planning vegan diets: children.
2001 Jun
Effect of UV irradiation on type I collagen fibril formation in neutral collagen solutions.
2001 Jun
The solution structure of the N-terminal domain of riboflavin synthase.
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
Stable histone deacetylase complexes distinguished by the presence of SANT domain proteins CoREST/kiaa0071 and Mta-L1.
2001 Mar 2
Stoichiometric growth model for riboflavin-producing Bacillus subtilis.
2001 Sep
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 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
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
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
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
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
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
LIVERTOX NBK548710
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WHO-ATC A11HA04
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JECFA EVALUATION INS-101(III)
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LOINC 6695-1
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DSLD 2543 (Number of products:6659)
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LOINC 27099-1
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WHO-ESSENTIAL MEDICINES LIST 27
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LOINC 49038-3
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NCI_THESAURUS C45812
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FDA ORPHAN DRUG 352511
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FDA ORPHAN DRUG 344911
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LOINC 18374-9
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LOINC 2924-9
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DSLD 203 (Number of products:536)
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CODEX ALIMENTARIUS (GSFA) INS-101(I)
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
FDA ORPHAN DRUG 468414
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WHO-ATC S01XA26
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CFR 21 CFR 184.1695
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CODEX ALIMENTARIUS (GSFA) INS-101(III)
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
LOINC 73723-9
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
Code System Code Type Description
HSDB
817
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
PUBCHEM
493570
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
CHEBI
17015
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
JECFA EVALUATION
INS-101(I)
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
RIBOFLAVIN
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
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.
SMS_ID
100000089010
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
EPA CompTox
DTXSID8021777
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PRIMARY
NSC
33298
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PRIMARY
CHEBI
176838
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
FDA UNII
TLM2976OFR
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
NCI_THESAURUS
C808
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
RS_ITEM_NUM
1603006
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
WIKIPEDIA
Riboflavin
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-507-1
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PRIMARY
MESH
D012256
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PRIMARY
ChEMBL
CHEMBL1534
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PRIMARY
EVMPD
SUB10298MIG
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PRIMARY
INN
419
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PRIMARY
WIKIPEDIA
RIBOFLAVIN
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
DAILYMED
TLM2976OFR
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY
MERCK INDEX
m9595
Created by admin on Fri Dec 15 15:06:49 GMT 2023 , Edited by admin on Fri Dec 15 15:06:49 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
2834
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PRIMARY
CAS
83-88-5
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PRIMARY
CHEBI
57986
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PRIMARY
RXCUI
9346
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PRIMARY RxNorm
DRUG BANK
DB00140
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PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
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