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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19N4O6.Na
Molecular Weight 398.3457
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIBOFLAVIN SODIUM

SMILES

[Na+].CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO)C3=NC(=O)[N-]C(=O)C3=N2

InChI

InChIKey=YXJHJCDOUFKMBG-BMZHGHOISA-M
InChI=1S/C17H20N4O6.Na/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);/q;+1/p-1/t11-,12+,14-;/m0./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C17H19N4O6
Molecular Weight 375.356
Charge -1
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
An improved photochemical method for the rapid spectrophotometric detection of superoxide dismutase.
2001
Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.
2001
[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis].
2001
[Effects of biologically active supplements on the antioxidant and vitamin status of patients with hypertension and ischemic heart disease].
2001
The stressed synovium.
2001
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
Effect of photosensitizer riboflavin on the fate of 2,4,6-trinitrotoluene in a freshwater environment.
2001 Aug
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
An unusual photohaemolytic property of riboflavin.
2001 Jan
Carrier-mediated transport of riboflavin in Ashbya gossypii.
2001 Jan
Thermostable alpha-amylase production by an extreme thermophile Bacillus thermooleovorans.
2001 Jan
Porcine Choroid plexus epithelial cells in culture: regulation of barrier properties and transport processes.
2001 Jan 1
Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae).
2001 Jan-Feb
Riboflavin treatment of antiretroviral induced lactic acidosis and hepatic steatosis.
2001 Jul
Structures of coenzyme F(420) in Mycobacterium species.
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
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
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
B vitamins induce an antinociceptive effect in the acetic acid and formaldehyde models of nociception in mice.
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
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
Hexavalent chromium stimulation of riboflavin synthesis in flavinogenic yeast.
2001 Mar
Simultaneous determination of thiamin and riboflavin in mushrooms by liquid chromatography.
2001 Mar
Steady-state and time-resolved spectroscopy of F420 extracted from methanogen cells and its utility as a marker for fecal contamination.
2001 Mar
Recurrent cleft lip and palate in siblings of a patient with malabsorption syndrome, probably caused by hypovitaminosis a associated with folic acid and vitamin B(2) deficiencies.
2001 Mar
Assessment of gastric acidity of Japanese subjects over the last 15 years.
2001 Mar
Characterization of chicken riboflavin carrier protein gene structure and promoter regulation by estrogen.
2001 Mar
Direct voltammetry for vitamin B(2) determination in aqueous solution by using glassy carbon electrode.
2001 Mar
Stable histone deacetylase complexes distinguished by the presence of SANT domain proteins CoREST/kiaa0071 and Mta-L1.
2001 Mar 2
Antioxidant activity of brahma rasayana.
2001 May
Potential for creatine and other therapies targeting cellular energy dysfunction in neurological disorders.
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
Nutritional assessment in various stages of liver cirrhosis.
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
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 15:22:53 GMT 2023
Edited
by admin
on Fri Dec 15 15:22:53 GMT 2023
Record UNII
04SRR95RP8
Record Status Validated (UNII)
Record Version
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Name Type Language
RIBOFLAVIN SODIUM
WHO-DD  
Common Name English
Riboflavin sodium [WHO-DD]
Common Name English
RIBOFLAVIN MONOSODIUM
Common Name English
SODIUM RIBOFLAVIN
Common Name English
RIBOFLAVINE, SODIUM SALT
Common Name English
Code System Code Type Description
DRUG BANK
DBSALT002842
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
SMS_ID
100000176159
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
RXCUI
2109051
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
CHEBI
176853
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
CAS
7681-29-0
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
04SRR95RP8
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
DAILYMED
04SRR95RP8
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID00998130
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
PUBCHEM
76964699
Created by admin on Fri Dec 15 15:22:54 GMT 2023 , Edited by admin on Fri Dec 15 15:22:54 GMT 2023
PRIMARY
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