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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H20N4O9P.Na.2H2O
Molecular Weight 514.3562
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIBOFLAVIN 5'-PHOSPHATE SODIUM DIHYDRATE

SMILES

O.O.[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=LQVGUKOCMOKKJU-QPVGXXQTSA-M
InChI=1S/C17H21N4O9P.Na.2H2O/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);;2*1H2/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 C17H21N4O9P
Molecular Weight 456.3438
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Curator's Comment: Penetrant in rabbits

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Thymidylate synthase-dihydrofolate reductase, Cryptosporidium hominis
55.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Infuvite Adult

Approved Use

Infuvite Adult is indicated for the prevention of vitamin deficiency in adults and children aged 11 and older receiving parenteral nutrition

Launch Date

1.05563521E12
Primary
Cytoflavin

Approved Use

Indicated for the treatment of consequences of cerebral infarction, for the treatment of atherosclerosis, encephalopathy, neurasthenia
Primary
Cytoflavin

Approved Use

Indicated for the treatment of consequences of cerebral infarction, for the treatment of atherosclerosis, encephalopathy, neurasthenia
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1209.4 nM
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
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
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
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
532.1 nM × h
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
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
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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Nutritional status and physical working capacity.
1982
Riboflavin status in infants born in rural Gambia, and the effect of a weaning food supplement.
1982
The effect of periconceptional supplementation on blood vitamin concentrations in women at recurrence risk for neural tube defect.
1983 Mar
Comparison of riboflavin, vitamin A, and zinc status of Chinese populations at high and low risk for esophageal cancer.
1985
Analgesic and antidepressive effects of low-dose amitriptyline in relation to its metabolism in patients with chronic pain.
1986 Feb
Urinary riboflavin excretion and erythrocyte glutathione reductase activity in preschool children suffering from upper respiratory infections and measles.
1987
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
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
Riboflavin levels in maternal milk: the influence of vitamin B2 status during the third trimester of pregnancy.
1999 Aug
Elevation of serum riboflavin carrier protein in breast cancer.
1999 Nov
Predictors of micronutrient status among six- to twelve-month-old breast-fed Ghanaian infants.
2000 Feb
Longitudinal vitamin and homocysteine levels in normal pregnancy.
2001 Jan
Abnormal vitamin levels in patients receiving home total parenteral nutrition.
2001 Nov-Dec
Anti-oxidant vitamins and steroid responsive nephrotic syndrome in Indian children.
2002 Oct
[Nested case-control study on riboflavin levels in blood and urine and the risk of lung cancer].
2003 Nov
FKF1 is essential for photoperiodic-specific light signalling in Arabidopsis.
2003 Nov 20
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
Patents

Sample Use Guides

In Vivo Use Guide
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
Flavin mononucleotide inhibited Cryptosporidium hominis TS-DHFR with IC50 55 uM
Substance Class Chemical
Created
by admin
on Sat Dec 16 14:13:11 UTC 2023
Edited
by admin
on Sat Dec 16 14:13:11 UTC 2023
Record UNII
20RD1DZH99
Record Status Validated (UNII)
Record Version
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Name Type Language
RIBOFLAVIN 5'-PHOSPHATE SODIUM DIHYDRATE
Common Name English
RIBOFLAVIN 5'-PHOSPHATE SODIUM
FCC   ORANGE BOOK   USP  
Preferred Name English
RIBOFLAVIN 5'-(DIHYDROGEN PHOSPHATE), SODIUM SALT, HYDRATE (1:1:2)
Systematic Name English
PHOSPHATED RIBOFLAVIN
USP-RS  
Common Name English
VITAMIN B2 PHOSPHATE (SODIUM SALT) DIHYDRATE
Common Name English
RIBOFLAVIN 5'-PHOSPHATE SODIUM [ORANGE BOOK]
Common Name English
RIBOFLAVIN SODIUM PHOSPHATE DIHYDRATE
Common Name English
RIBOFLAVIN PHOSPHATE SODIUM [VANDF]
Common Name English
RIBOFLAVIN 5'-PHOSPHATE SODIUM [FCC]
Common Name English
RIBOFLAVINE 5'-(SODIUM HYDROGEN PHOSPHATE), DIHYDRATE
Common Name English
RIBOFLAVIN 5'-PHOSPHATE SODIUM [USP MONOGRAPH]
Common Name English
FLAVIN MONONUCLEOTIDE DIHYDRATE
Common Name English
SODIUM RIBOFLAVIN 5'-PHOSPHATE DIHYDRATE
Common Name English
PHOSPHATED RIBOFLAVIN [USP-RS]
Common Name English
RIBOFLAVIN PHOSPHATE SODIUM
VANDF  
Common Name English
COLLAGEX-RAPID COMPONENT RIBOFLAVIN 5'-PHOSPHATE SODIUM
Brand Name English
COLLAGEX-HYPOTONIC COMPONENT RIBOFLAVIN 5'-PHOSPHATE SODIUM
Brand Name English
RIBOFLAVIN 5'-(DIHYDROGEN PHOSPHATE), MONOSODIUM SALT, DIHYDRATE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 812721
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
NCI_THESAURUS C26017
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1201794
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
CAS
6184-17-4
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
FDA UNII
20RD1DZH99
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
DRUG BANK
DBSALT000877
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
RXCUI
2611697
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
DAILYMED
20RD1DZH99
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
EVMPD
SUB23539
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
SMS_ID
100000089013
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
EVMPD
SUB04238MIG
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
RS_ITEM_NUM
1535700
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
PUBCHEM
23687712
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
NCI_THESAURUS
C48016
Created by admin on Sat Dec 16 14:13:12 UTC 2023 , Edited by admin on Sat Dec 16 14:13:12 UTC 2023
PRIMARY
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