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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

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
Elevation of serum riboflavin carrier protein in breast cancer.
1999 Nov
[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
Determination of riboflavin, flavin mononucletide and flavin adenine dinucleotide in biological tissues by capillary zone electrophoresis and laser-induced fluorescence detection.
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
Reagentless chemiluminescence flow sensor for the determination of riboflavin in pharmaceutical preparations and human urine.
2001 Aug
Longitudinal vitamin and homocysteine levels in normal pregnancy.
2001 Jan
Crystal structure of 3,4-dihydroxy-2-butanone 4-phosphate synthase of riboflavin biosynthesis.
2001 Jan 10
Riboflavin treatment of antiretroviral induced lactic acidosis and hepatic steatosis.
2001 Jul
Structures of coenzyme F(420) in Mycobacterium species.
2001 Jul
Long-term nutrient intake and early age-related nuclear lens opacities.
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
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
19F NMR ligand perturbation studies on 6,7-bis(trifluoromethyl)-8-ribityllumazine-7-hydrates and the lumazine synthase complex of Bacillus subtilis. Site-directed mutagenesis changes the mechanism and the stereoselectivity of the catalyzed haloform-type reaction.
2001 Jun 1
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
Hexavalent chromium stimulation of riboflavin synthesis in flavinogenic yeast.
2001 Mar
Assessment of gastric acidity of Japanese subjects over the last 15 years.
2001 Mar
Antioxidant activity of brahma rasayana.
2001 May
Crystal structure of riboflavin synthase.
2001 May 9
[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
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
A Plackett-Burnam screening design directs the efficient formulation of multicomponent DRV liposomes.
2001 Sep
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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:22:53 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
SMS_ID
100000176159
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
RXCUI
2109051
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
CHEBI
176853
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
CAS
7681-29-0
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
04SRR95RP8
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
DAILYMED
04SRR95RP8
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID00998130
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
PUBCHEM
76964699
Created by admin on Fri Dec 15 15:22:54 UTC 2023 , Edited by admin on Fri Dec 15 15:22:54 UTC 2023
PRIMARY
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