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Flavin mononucleotide

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Flavin mononucleotide
Skeletal formula of flavin mononucleotide
Ball-and-stick model of the flavin mononucleotide molecule
Names
IUPAC name
1-Deoxy-1-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-D-ribitol 5-(dihydrogen phosphate)
Systematic IUPAC name
(2R,3S,4S)-5-(7,8-Dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen phosphate
Other names
  • FMN
  • Epioxa
  • Epioxa HD
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.150 Edit this at Wikidata
E number E101a (colours)
MeSH Flavin+mononucleotide
UNII
  • 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
    Key: FVTCRASFADXXNN-SCRDCRAPSA-N
  • Cc1cc2c(cc1C)n(c-3nc(=O)[nH]c(=O)c3n2)C[C@@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)O
Properties
C17H21N4O9P
Molar mass 456.344 g/mol
Melting point 195 °C
Pharmacology
S01XA26 (WHO)
Ophthalmic
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Flavin mononucleotide (FMN), or riboflavin-5′-phosphate, is a biomolecule produced from riboflavin (vitamin B2) by the enzyme riboflavin kinase and functions as the prosthetic group of various oxidoreductases, including NADH dehydrogenase, as well as a cofactor in biological blue-light photo receptors.[2] During the catalytic cycle, various oxidoreductases induce reversible interconversions between the oxidized (FMN), semiquinone (FMNH•), and reduced (FMNH2) forms of the isoalloxazine core. FMN is a stronger oxidizing agent than NAD and is particularly useful because it can take part in both one- and two-electron transfers. In its role as blue-light photo receptor, (oxidized) FMN stands out from the 'conventional' photo receptors as the signaling state and not an E/Z isomerization.

It is the principal form in which riboflavin is found in cells and tissues. It requires more energy to produce, but is more soluble than riboflavin. In cells, FMN occurs freely circulating but also in several covalently bound forms.[3] Covalently or non-covalently bound FMN is a cofactor of many enzymes playing an important pathophysiological role in cellular metabolism. For example dissociation of flavin mononucleotide from mitochondrial complex I has been shown to occur during ischemia/reperfusion brain injury during stroke.[4][5]

Food additive

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Flavin mononucleotide is also used as an orange-red food colour additive, designated in Europe as E number E101a.[6]

E106, a very closely related food dye, is riboflavin-5′-phosphate sodium salt, which consists mainly of the monosodium salt of the 5′-monophosphate ester of riboflavin. It is rapidly turned to free riboflavin after ingestion. It is found in many foods for babies and young children as well as jams, milk products, and sweets and sugar products.[7]

Medical uses

[edit]
Flavin mononucleotide
Clinical data
AHFS/Drugs.comEpioxa
License data
Identifiers
DrugBank
E numberE101a (colours) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.005.150 Edit this at Wikidata

Riboflavin 5'-phosphate (Epioxa) and riboflavin 5’-phosphate sodium (Epioxa HD) and are photoenhancers that are indicated for use in epithelium-on corneal collagen cross-linking for the treatment of keratoconus in people aged thirteen years of age and older, in conjunction with the O2n System and the Boost Goggles.[1]

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.[8] Riboflavin 5'-phosphate sodium is a mixture of the sodium salts of riboflavin, riboflavin monophosphates, and riboflavin diphosphates.[1]

Epioxa and Epioxa HD were approved for medical use in the United States in October 2025.[9]

See also

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References

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  1. ^ a b c "Prescribing information for Epioxa HD and Epioxa" (PDF). fda.gov.
  2. ^ Tsibris JC, McCormick DB, Wright LD (March 1966). "Studies on the binding and function of flavin phosphates with flavin mononucleotide-dependent enzymes". The Journal of Biological Chemistry. 241 (5): 1138–1143. doi:10.1016/S0021-9258(18)96813-4. PMID 4379862.
  3. ^ Mewies M, McIntire WS, Scrutton NS (January 1998). "Covalent attachment of flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN) to enzymes: the current state of affairs". Protein Science. 7 (1): 7–20. doi:10.1002/pro.5560070102. PMC 2143808. PMID 9514256.
  4. ^ Kahl A, Stepanova A, Konrad C, Anderson C, Manfredi G, Zhou P, et al. (May 2018). "Critical Role of Flavin and Glutathione in Complex I-Mediated Bioenergetic Failure in Brain Ischemia/Reperfusion Injury". Stroke. 49 (5): 1223–1231. doi:10.1161/STROKEAHA.117.019687. PMC 5916474. PMID 29643256.
  5. ^ Galkin A (November 2019). "Brain Ischemia/Reperfusion Injury and Mitochondrial Complex I Damage". Biochemistry. Biokhimiia. 84 (11): 1411–1423. doi:10.1134/S0006297919110154. PMID 31760927. S2CID 207990089.
  6. ^ "Current EU approved additives and their E Numbers", Food Standards Agency website, retrieved 15 December 2011
  7. ^ Turck D, Bresson JL, Burlingame B, Dean T, Fairweather-Tait S, Heinonen M, et al. (August 2017). "Dietary Reference Values for riboflavin". EFSA Journal. European Food Safety Authority. 15 (8): e04919. doi:10.2903/j.efsa.2017.4919. PMC 7010026. PMID 32625611.
  8. ^ "Riboflavin 5'-phosphate". Inxight Drugs. 24 September 2004. Retrieved 21 October 2025. Public Domain This article incorporates text from this source, which is in the public domain.
  9. ^ "Glaukos Announces FDA Approval of Epioxa" (Press release). Glaukos. 20 October 2025. Retrieved 21 October 2025.
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