Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H20N4O9P.Na |
Molecular Weight | 478.3256 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)([O-])=O)C3=NC(=O)NC(=O)C3=N2
InChI
InChIKey=OHSHFZJLPYLRIP-BMZHGHOISA-M
InChI=1S/C17H21N4O9P.Na/c1-7-3-9-10(4-8(7)2)21(15-13(18-9)16(25)20-17(26)19-15)5-11(22)14(24)12(23)6-30-31(27,28)29;/h3-4,11-12,14,22-24H,5-6H2,1-2H3,(H,20,25,26)(H2,27,28,29);/q;+1/p-1/t11-,12+,14-;/m0./s1
Molecular Formula | C17H20N4O9P |
Molecular Weight | 455.3359 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
DescriptionCurator's Comment: Description was created based on several sources, including http://rupharma.com/cytoflavin/ and https://ods.od.nih.gov/factsheets/Riboflavin-HealthProfessional/
Curator's Comment: Description was created based on several sources, including http://rupharma.com/cytoflavin/ and https://ods.od.nih.gov/factsheets/Riboflavin-HealthProfessional/
Flavin mononucleotide, or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin by the enzyme riboflavin kinase and functions as prosthetic group of various oxidoreductases including NADH dehydrogenase as well as cofactor in biological blue-light photo receptors. Riboflavin (Vitamin B 2) (as riboflavin 5-phosphate sodium) is an ingredient of the FDA approved composition Infuvite Adult, indicated as a daily multivitamin maintenance supplement for adults and children aged 11 and older receiving parenteral nutrition. Infuvite Adult is also indicated in other situations where administration by the intravenous route is required. Such situations include surgery, extensive burns, fractures and other trauma, severe infectious diseases, and comatose states, which may provoke a “stress” situation with profound alterations in the body’s metabolic demands and consequent tissue depletion of nutrients. Flavin mononucleotide is also a component of Cytoflavin, used for the treatment of consequences of cerebral infarction, for the treatment of atherosclerosis, encephalopathy, neurasthenia. Cytoflavin is marketed in Russian Federation.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/7452254
Curator's Comment: Penetrant in rabbits
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Thymidylate synthase-dihydrofolate reductase, Cryptosporidium hominis Sources: http://www.ncbi.nlm.nih.gov/pubmed/19059777 |
55.0 µM [IC50] | ||
Target ID: GO:0006116 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26721206 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Infuvite Adult Approved UseInfuvite Adult is indicated for the prevention of vitamin deficiency in adults and children aged 11 and older receiving parenteral nutrition Launch Date2003 |
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Sources: http://rupharma.com/cytoflavin/ |
Primary | Cytoflavin Approved UseIndicated for the treatment of consequences of cerebral infarction, for the treatment of atherosclerosis, encephalopathy, neurasthenia |
||
Sources: http://rupharma.com/cytoflavin/ |
Primary | Cytoflavin Approved UseIndicated for the treatment of consequences of cerebral infarction, for the treatment of atherosclerosis, encephalopathy, neurasthenia |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1209.4 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8604671/ |
11.6 mg single, intravenous dose: 11.6 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
RIBOFLAVIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
206.7 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8604671/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIBOFLAVIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
308.2 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8604671/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIBOFLAVIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
217.7 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/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 |
---|---|---|---|---|
532.1 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8604671/ |
11.6 mg single, intravenous dose: 11.6 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
RIBOFLAVIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
886.4 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8604671/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIBOFLAVIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
981.6 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8604671/ |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
RIBOFLAVIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
883.9 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/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 |
PubMed
Title | Date | PubMed |
---|---|---|
Nutritional status and physical working capacity. | 1982 |
|
Riboflavin status in infants born in rural Gambia, and the effect of a weaning food supplement. | 1982 |
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Comparison of riboflavin, vitamin A, and zinc status of Chinese populations at high and low risk for esophageal cancer. | 1985 |
|
Urinary riboflavin excretion and erythrocyte glutathione reductase activity in preschool children suffering from upper respiratory infections and measles. | 1987 |
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Vitamin concentrations in very low birth weight infants given vitamins intravenously in a lipid emulsion: measurement of vitamins A, D, and E and riboflavin. | 1988 Dec |
|
Bioavailability of riboflavin from fortified palm juice. | 1989 Dec |
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Urinary riboflavin excretion after a load test in rural China as a measure of possible riboflavin deficiency. | 1990 Mar |
|
Folic acid, riboflavin, thiamine, and vitamin B-6 status of a group of first-time blood donors. | 1998 Nov |
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Elevation of serum riboflavin carrier protein in breast cancer. | 1999 Nov |
|
Abnormal vitamin levels in patients receiving home total parenteral nutrition. | 2001 Nov-Dec |
|
[Nested case-control study on riboflavin levels in blood and urine and the risk of lung cancer]. | 2003 Nov |
|
Improving the bacteriological safety of platelet transfusions. | 2004 Jan |
|
Separation, identification and quantification of riboflavin and its photoproducts in blood products using high-performance liquid chromatography with fluorescence detection: a method to support pathogen reduction technology. | 2004 Nov-Dec |
|
Efficacy of twice-weekly multiple micronutrient supplementation for improving the hemoglobin and micronutrient status of anemic adolescent schoolgirls in Bangladesh. | 2005 Oct |
|
Identification and functional characterization of rat riboflavin transporter 2. | 2009 Apr |
|
Involvement of riboflavin kinase expression in cellular sensitivity against cisplatin. | 2011 Apr |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/infuvite-adult.html
Curator's Comment: Can also be taken orally in Cytoflavin formulation http://vitamedd.com/en/pages/1342999
The starting dose of Infuvite Adult is one 10 mL daily dose that is prepared by transferring the content of vial 1 into the content of vial 2 to provide 10 single doses. One 10 mL dose is then added directly to the intravenous fluid. Patients with multiple vitamin deficiencies or with increased vitamin requirements may need multiple daily dosages as indicated.
Each 5 mL of Vial 1* contains 3.6 mg of Riboflavin (Vitamin B 2) (as riboflavin 5-phosphate sodium)
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19059777
Flavin mononucleotide inhibited Cryptosporidium hominis TS-DHFR with IC50 55 uM
Substance Class |
Chemical
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Record UNII |
957E53WV42
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Record Status |
Validated (UNII)
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INS-101(II)
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INS-101(II)
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m5393
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23666409
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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SOLVATE->ANHYDROUS |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
riboflavin sodium phosphate impurity B [EP] amount not specified, but sum of riboflavin sodium phosphate impurities A, B and C: maximum 6.0 per cent (dried substance)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
RIBOFLAVIN SODIUM PHOSPHATE IMPURITY E [EP] AMOUNT NOT SPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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