RIBOFLAVIN

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/203324s000lbl.pdf
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

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Progressive keratoconus 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/203324s000lbl.pdf	Primary		Approved 8429	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
Corneal ectasia 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/203324s000lbl.pdf	Primary		Approved 8429	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

C_max

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

T_1/2

Value	Dose	Co-administered	Analyte	Population
66 min OTHER GOV https://www.glowm.com/resources/glowm/cd/pages/drugs/qr016.html	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

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17015	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17015
ChemicalBook	CB4383318	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4383318
MolPort	MolPort-003-934-329	https://www.molport.com/shop/molecule-link/MolPort-003-934-329
Selleck Chemicals	Riboflavin-Vitamin-B2	http://www.selleckchem.com/products/Riboflavin-Vitamin-B2.html
ZINC	ZINC000002036848	http://zinc15.docking.org/substances/ZINC000002036848
eMolecules	711592	https://www.emolecules.com/cgi-bin/more?vid=711592

PubMed

Title	Date	PubMed
In vivo expression of the collagen-related heat shock protein HSP47, following hyperthermia or photodynamic therapy.	2001	11482817
Extracting biological information from DNA arrays: an unexpected link between arginine and methionine metabolism in Bacillus subtilis.	2001	11423008
[Effects of biologically active supplements on the antioxidant and vitamin status of patients with hypertension and ischemic heart disease].	2001	11338339
The stressed synovium.	2001	11178114
The enhancement of riboflavin-mediated photo-oxidation of doxorubicin by histidine and urocanic acid.	2001 Apr	11345651
Possible cause of G-C-->C-G transversion mutation by guanine oxidation product, imidazolone.	2001 Apr	11325592
Modeling and experimental design for metabolic flux analysis of lysine-producing Corynebacteria by mass spectrometry.	2001 Apr	11289793
Site-specific DNA damage at the GGG sequence by UVA involves acceleration of telomere shortening.	2001 Apr 17	11294644
Biosynthesis of riboflavin. The reaction catalyzed by 6,7-dimethyl-8-ribityllumazine synthase can proceed without enzymatic catalysis under physiological conditions.	2001 Apr 20	11304170
Photosensitizer initiated attacks on DNA under dry conditions and their inhibition: a DNA archiving issue.	2001 Aug 15	11485843
Longitudinal vitamin and homocysteine levels in normal pregnancy.	2001 Jan	11227033
Crystal structure of 3,4-dihydroxy-2-butanone 4-phosphate synthase of riboflavin biosynthesis.	2001 Jan 10	11342130
Marginal vitamin and mineral intake of Costa Rican adolescents.	2001 Jan-Feb	11282184
Nutritional composition of uncommon foods and their role in meeting micronutrient needs.	2001 Jul	11474897
Long-term nutrient intake and early age-related nuclear lens opacities.	2001 Jul	11448323
Use of vitamin supplements and cataract: the Blue Mountains Eye Study.	2001 Jul	11438049
Riboflavin uptake in human trophoblast-derived BeWo cell monolayers: cellular translocation and regulatory mechanisms.	2001 Jul	11408551
The effects of thyroxine isomers on free-radical oxidation processes in subcellular fractions of rat cerebral cortex.	2001 Jul-Aug	11508500
Vitamin B intake and status in healthy Havanan men, 2 years after the Cuban neuropathy epidemic.	2001 Jun	11430779
[Energy and nutrient intake in compulsory high school students].	2001 Jun	11412401
B vitamins induce an antinociceptive effect in the acetic acid and formaldehyde models of nociception in mice.	2001 Jun 15	11516431
Relationships between dietary intake and cognitive function level in Korean elderly people.	2001 Mar	11406779
Limiting light-induced lipid peroxidation and vitamin loss in infant parenteral nutrition by adding multivitamin preparations to Intralipid.	2001 Mar	11332161
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	11283973
[Effect of coenzyme Q10 in patients with kidney diseases].	2001 May 24	11411060
Mechanism of the fluorescent light induced suppression of Curly phenotype in Drosophila melanogaster.	2001 Sep	11536279
Crystallization and preliminary crystallographic analysis of the recombinant N-terminal domain of riboflavin synthase.	2001 Sep	11526324
Metabolic flux analysis with a comprehensive isotopomer model in Bacillus subtilis.	2001 Sep	11505384
A Plackett-Burnam screening design directs the efficient formulation of multicomponent DRV liposomes.	2001 Sep	11470202
Biosynthesis of the phosphodiester bond in coenzyme F(420) in the methanoarchaea.	2001 Sep 11	11535063

Patents

Sample Use Guides

In Vivo Use Guide

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

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 UTC 2023` Edited by `admin` on `Fri Dec 15 15:06:49 UTC 2023`
Record UNII	TLM2976OFR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIBOFLAVIN

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

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

Common Name

English

RIBOFLAVIN [HSDB]

Common Name

English

RIBOFLAVIN [FCC]

Common Name

English

RIBOFLAVINUM

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