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

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
In vivo expression of the collagen-related heat shock protein HSP47, following hyperthermia or photodynamic therapy.
2001
[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis].
2001
Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human.
2001
The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid.
2001 Apr
Natural therapies for ocular disorders, part two: cataracts and glaucoma.
2001 Apr
Riboflavin synthase of Escherichia coli. Effect of single amino acid substitutions on reaction rate and ligand binding properties.
2001 Apr 13
Reagentless chemiluminescence flow sensor for the determination of riboflavin in pharmaceutical preparations and human urine.
2001 Aug
Effect of photosensitizer riboflavin on the fate of 2,4,6-trinitrotoluene in a freshwater environment.
2001 Aug
Photosensitizer initiated attacks on DNA under dry conditions and their inhibition: a DNA archiving issue.
2001 Aug 15
An unusual photohaemolytic property of riboflavin.
2001 Jan
Longitudinal vitamin and homocysteine levels in normal pregnancy.
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
Protein-based chiral stationary phases for high-performance liquid chromatography enantioseparations.
2001 Jan 12
Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage.
2001 Jan 25
Marginal vitamin and mineral intake of Costa Rican adolescents.
2001 Jan-Feb
Alternative therapies in headache. Is there a role?
2001 Jul
Structures of coenzyme F(420) in Mycobacterium species.
2001 Jul
Effect of UV irradiation on type I collagen fibril formation in neutral collagen solutions.
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
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
Biosynthesis of riboflavin: studies on the mechanism of GTP cyclohydrolase II.
2001 Jun 22
Relationships between dietary intake and cognitive function level in Korean elderly people.
2001 Mar
Limiting light-induced lipid peroxidation and vitamin loss in infant parenteral nutrition by adding multivitamin preparations to Intralipid.
2001 Mar
Children's nutrient intake at preschool and at home.
2001 May
[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
Validity and reproducibility of a food frequency questionnaire for pregnant Finnish women.
2001 Sep 1
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
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
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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)
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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)
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LOINC 73723-9
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Code System Code Type Description
HSDB
817
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PRIMARY
PUBCHEM
493570
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PRIMARY
CHEBI
17015
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PRIMARY
JECFA EVALUATION
INS-101(I)
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PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
RIBOFLAVIN
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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
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PRIMARY
EPA CompTox
DTXSID8021777
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PRIMARY
NSC
33298
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PRIMARY
CHEBI
176838
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PRIMARY
FDA UNII
TLM2976OFR
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PRIMARY
NCI_THESAURUS
C808
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PRIMARY
RS_ITEM_NUM
1603006
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PRIMARY
WIKIPEDIA
Riboflavin
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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
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PRIMARY
DAILYMED
TLM2976OFR
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PRIMARY
MERCK INDEX
m9595
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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