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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H21N4O9P
Molecular Weight 456.3438
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIBOFLAVIN 5'-PHOSPHATE

SMILES

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=FVTCRASFADXXNN-SCRDCRAPSA-N
InChI=1S/C17H21N4O9P/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)/t11-,12+,14-/m0/s1

HIDE SMILES / InChI

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

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
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
Predictors of micronutrient status among six- to twelve-month-old breast-fed Ghanaian infants.
2000 Feb
FKF1 is essential for photoperiodic-specific light signalling in Arabidopsis.
2003 Nov 20
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 Fri Dec 15 15:01:56 UTC 2023
Edited
by admin
on Fri Dec 15 15:01:56 UTC 2023
Record UNII
7N464URE7E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLAVIN MONONUCLEOTIDE
MI  
Preferred Name English
RIBOFLAVIN 5'-PHOSPHATE
Common Name English
VITAMIN B2 (RIBOFLAVIN-5-PHOSPHATE)
Common Name English
RIBOFLAVIN PHOSPHATE [VANDF]
Common Name English
FMN
Common Name English
VITAMIN B2 PHOSPHATE
Common Name English
Riboflavin phosphate [WHO-DD]
Common Name English
FLAVIN MONONUCLEOTIDE [MI]
Common Name English
RIBOFLAVIN PHOSPHATE
VANDF   WHO-DD  
Common Name English
RIBOFLAVIN 5'-(DIHYDROGEN PHOSPHATE)
Common Name English
Classification Tree Code System Code
LOINC 53648-2
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
FDA ORPHAN DRUG 342311
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
DSLD 4337 (Number of products:1)
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
DSLD 203 (Number of products:536)
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
LOINC 79393-5
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
NCI_THESAURUS C26017
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
Code System Code Type Description
DRUG BANK
DB03247
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
PUBCHEM
643976
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
NCI_THESAURUS
C61925
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
EVMPD
SUB35224
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
CAS
146-17-8
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
RXCUI
1925821
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
MESH
D005486
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
CHEBI
17621
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
FDA UNII
7N464URE7E
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID8023559
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
EVMPD
SUB35561
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
MERCK INDEX
m5393
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
FLAVIN MONONUCLEOTIDE
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
DRUG CENTRAL
2374
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
DAILYMED
7N464URE7E
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
SMS_ID
100000128322
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-664-7
Created by admin on Fri Dec 15 15:01:56 UTC 2023 , Edited by admin on Fri Dec 15 15:01:56 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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PARENT -> METABOLITE ACTIVE
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ACTIVE MOIETY