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
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
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22406738
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
Condition | Modality | Targets | Highest Phase | Product |
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Primary | PHOTREXA Approved UsePHOTREXA® 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 Date2016 |
|||
Primary | PHOTREXA Approved UsePHOTREXA® 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 Date2016 |
Cmax
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Title | Date | PubMed |
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In vivo expression of the collagen-related heat shock protein HSP47, following hyperthermia or photodynamic therapy. | 2001 |
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[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis]. | 2001 |
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Influence of a probiotic yoghurt on the status of vitamins B(1), B(2) and B(6) in the healthy adult human. | 2001 |
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The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid. | 2001 Apr |
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Natural therapies for ocular disorders, part two: cataracts and glaucoma. | 2001 Apr |
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Riboflavin synthase of Escherichia coli. Effect of single amino acid substitutions on reaction rate and ligand binding properties. | 2001 Apr 13 |
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Reagentless chemiluminescence flow sensor for the determination of riboflavin in pharmaceutical preparations and human urine. | 2001 Aug |
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Effect of photosensitizer riboflavin on the fate of 2,4,6-trinitrotoluene in a freshwater environment. | 2001 Aug |
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Photosensitizer initiated attacks on DNA under dry conditions and their inhibition: a DNA archiving issue. | 2001 Aug 15 |
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An unusual photohaemolytic property of riboflavin. | 2001 Jan |
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Longitudinal vitamin and homocysteine levels in normal pregnancy. | 2001 Jan |
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Nutritional evaluation of some processed catering foods. | 2001 Jan |
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Porcine Choroid plexus epithelial cells in culture: regulation of barrier properties and transport processes. | 2001 Jan 1 |
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Crystal structure of 3,4-dihydroxy-2-butanone 4-phosphate synthase of riboflavin biosynthesis. | 2001 Jan 10 |
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Protein-based chiral stationary phases for high-performance liquid chromatography enantioseparations. | 2001 Jan 12 |
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Mut-Test to detect substances suppressing spontaneous mutation due to oxidative damage. | 2001 Jan 25 |
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Marginal vitamin and mineral intake of Costa Rican adolescents. | 2001 Jan-Feb |
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Alternative therapies in headache. Is there a role? | 2001 Jul |
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Structures of coenzyme F(420) in Mycobacterium species. | 2001 Jul |
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Effect of UV irradiation on type I collagen fibril formation in neutral collagen solutions. | 2001 Jun |
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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 |
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The solution structure of the N-terminal domain of riboflavin synthase. | 2001 Jun 15 |
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Riboflavin synthesis genes ribE, ribB, ribH, ribA reside in the lux operon of Photobacterium leiognathi. | 2001 Jun 15 |
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Light-dependent generation of reactive oxygen species in cell culture media. | 2001 Jun 15 |
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Biosynthesis of riboflavin: studies on the mechanism of GTP cyclohydrolase II. | 2001 Jun 22 |
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Relationships between dietary intake and cognitive function level in Korean elderly people. | 2001 Mar |
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Limiting light-induced lipid peroxidation and vitamin loss in infant parenteral nutrition by adding multivitamin preparations to Intralipid. | 2001 Mar |
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Children's nutrient intake at preschool and at home. | 2001 May |
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[Dietary and biochemical riboflavin status in a cohort of young people in the community of Madrid]. | 2001 May-Jun |
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Mechanism of the fluorescent light induced suppression of Curly phenotype in Drosophila melanogaster. | 2001 Sep |
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Validity and reproducibility of a food frequency questionnaire for pregnant Finnish women. | 2001 Sep 1 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27463630
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
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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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2543 (Number of products:6659)
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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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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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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. | ||
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100000089010
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Riboflavin
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RIBOFLAVIN
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TLM2976OFR
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m9595
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2834
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DB00140
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
SALT/SOLVATE (PARENT)