RIBOFLAVIN 5'-PHOSPHATE

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 Search

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2004/21163s011lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Thymidylate synthase-dihydrofolate reductase, Cryptosporidium hominis 3 Target ID: Thymidylate synthase-dihydrofolate reductase, Cryptosporidium hominis Sources: http://www.ncbi.nlm.nih.gov/pubmed/19059777	Inhibitor 8297		55.0 µM [IC50]
NADH oxidation 3 Target ID: GO:0006116 Sources: http://www.ncbi.nlm.nih.gov/pubmed/26721206	Oxidative Enzyme 3

Conditions

Condition	Modality	Highest Phase	Product
Vitamin deficiency 17 Sources: https://www.drugs.com/pro/infuvite-adult.html	Primary	Approved 8429	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
Cerebral infarction 14 Sources: http://rupharma.com/cytoflavin/	Primary	Approved 8429	Cytoflavin Approved Use Indicated for the treatment of consequences of cerebral infarction, for the treatment of atherosclerosis, encephalopathy, neurasthenia
Atherosclerosis 74 Sources: http://rupharma.com/cytoflavin/	Primary	Approved 8429	Cytoflavin Approved Use Indicated for the treatment of consequences of cerebral infarction, for the treatment of atherosclerosis, encephalopathy, neurasthenia

C_max

Value	Dose	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	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

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00IAUN
ABI Chem	AC1LD8D0
AK Scientific	S188
AK Scientific	X2938
AN PharmaTech	AN-23277
AbovChem LLC	HY-B0964
Alfa Chemistry	ACM22251850
Apollo Scientific	BIF4012
BLD Pharm	BD264519	http://www.bldpharm.com/products/146-17-8.html
BOC Sciences	130-40-5
BenchChem	B089457	https://www.benchchem.com/product/b089457
BioSynth	W-108348
Cayman Chemical	18167
Chem Scene	CS-0013780	http://www.chemscene.com/146-17-8.html
Chem-Impex International	259
Chemieliva Pharmaceutical Co., Ltd	PBCM1190390
Combi-Blocks	QB-4442
Compound Cloud	23666409
Compound Cloud	23687712
Compound Cloud	643976
DC Chemicals	DC12237	http://www.dcchemicals.com/product_show-Riboflavine_phosphate.html
Lab Seeker	SC-19205
MedChem Express	HY-B0964A	https://www.medchemexpress.com/Riboflavine_phosphate.html
MolPort	MolPort-003-939-021
MolPort	MolPort-004-964-255
MolPort	MolPort-016-582-614
Molnova	M11220
MuseChem	M067043
NovoSeek	643976
Parchem	39312	https://www.parchem.com/chemical-supplier-distributor/Riboflavin-5'-phosphate-039312.aspx
Ryan Scientific	Pizotifen
Selleck Chemicals	S5107
Sigma Aldrich	CDS020791\|ALDRICH
Sigma Aldrich	CDS025203\|ALDRICH
Sigma Aldrich	F2253\|SIGMA
Sigma Aldrich	F6750\|SIGMA
Sigma Aldrich	R0630000\|SIAL
Smolecule	S564790	https://www.smolecule.com/products/s564790
StruChem	SC-19205
THE BioTek	bt-364823	https://www.thebiotek.com/product/others/bt-364823
Tetrahedron	TS82909
Tetrahedron	TS83394
TimTec	SBB057412
TimTec	ST50999669
Toronto Research Chemicals	R415000
W&J PharmaChem	50C579481
ZINC	ZINC000003831425	http://zinc15.docking.org/substances/ZINC000003831425
eMolecules	108761523
eMolecules	205741990
eMolecules	43339210
eMolecules	6877149
eMolecules	76746566

PubMed

Title	Date	PubMed
Nutritional status and physical working capacity.	1982	7161138
Riboflavin status in infants born in rural Gambia, and the effect of a weaning food supplement.	1982	7101408
The effect of periconceptional supplementation on blood vitamin concentrations in women at recurrence risk for neural tube defect.	1983 Mar	6830748
Comparison of riboflavin, vitamin A, and zinc status of Chinese populations at high and low risk for esophageal cancer.	1985	3878498
Analgesic and antidepressive effects of low-dose amitriptyline in relation to its metabolism in patients with chronic pain.	1986 Feb	3510800
Urinary riboflavin excretion and erythrocyte glutathione reductase activity in preschool children suffering from upper respiratory infections and measles.	1987	3592624
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	3142982
Bioavailability of riboflavin from fortified palm juice.	1989 Dec	2631092
Urinary riboflavin excretion after a load test in rural China as a measure of possible riboflavin deficiency.	1990 Mar	2369885
Folic acid, riboflavin, thiamine, and vitamin B-6 status of a group of first-time blood donors.	1998 Nov	9808225
Riboflavin levels in maternal milk: the influence of vitamin B2 status during the third trimester of pregnancy.	1999 Aug	12038475
Elevation of serum riboflavin carrier protein in breast cancer.	1999 Nov	10566553
Predictors of micronutrient status among six- to twelve-month-old breast-fed Ghanaian infants.	2000 Feb	10720170
Longitudinal vitamin and homocysteine levels in normal pregnancy.	2001 Jan	11227033
Abnormal vitamin levels in patients receiving home total parenteral nutrition.	2001 Nov-Dec	11606856
Anti-oxidant vitamins and steroid responsive nephrotic syndrome in Indian children.	2002 Oct	12354259
[Nested case-control study on riboflavin levels in blood and urine and the risk of lung cancer].	2003 Nov	14963913
FKF1 is essential for photoperiodic-specific light signalling in Arabidopsis.	2003 Nov 20	14628054
Improving the bacteriological safety of platelet transfusions.	2004 Jan	14689374
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	15382964
Efficacy of twice-weekly multiple micronutrient supplementation for improving the hemoglobin and micronutrient status of anemic adolescent schoolgirls in Bangladesh.	2005 Oct	16210713
Identification and functional characterization of rat riboflavin transporter 2.	2009 Apr	19122205
Involvement of riboflavin kinase expression in cellular sensitivity against cisplatin.	2011 Apr	21308351

Patents

Sample Use Guides

In Vivo Use Guide

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

Name

Type

Language

FLAVIN MONONUCLEOTIDE

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

Common Name

English

RIBOFLAVIN 5'-(DIHYDROGEN PHOSPHATE)

Common Name

English

Classification Tree Code System Code

LOINC

53648-2