Phytomenadione

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Phylloquinone
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Phytomenadione
intravenous
ATC code
Legal status
Legal status
Identifiers
  • 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
JSmol)
  • CC1=C(C(=O)c2ccccc2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
  • InChI=1S/C31H46O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1 checkY
  • Key:MBWXNTAXLNYFJB-NKFFZRIASA-N

Phytomenadione, also known as vitamin K1 or phylloquinone, is a vitamin found in food and used as a dietary supplement.[4][5] It is on the World Health Organization's List of Essential Medicines.[6]

It is used to treat certain

injection under the skin.[5] When given by injection benefits are seen within two hours.[5] It is also recommended for preventing and treating vitamin K deficiency bleeding (VKDB) in infants.[5] Many countries in the world choose intramuscular injections in newborn to keep them safe from VKDB. It is considered a safe treatment and saves many children from death and severe neurologic deficit every year.[7]

Side effects when given by injection may include pain at the site of injection.

green vegetables, vegetable oil, and some fruit.[11]

Phytomenadione was first isolated in 1939.

Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery.[12]

Terminology

Phytomenadione is often also called phylloquinone, vitamin K,[13] or phytonadione.

A

stereoisomer of phylloquinone is called vitamin k1 (note the difference in capitalization).[citation needed
]

Medical uses

See also: Vitamin K § Medical uses (the section nearly only covers Vitamin K1, i.e. this compound.)

It is used to treat certain

obstructive jaundice.[5] It is used to prevent and treat vitamin K deficiency bleeding (VKDB) in infants.[5]

In Canada, phytomenadione (Hemophyt) is indicated for the treatment of anticoagulant poisoning in dogs.[2][3]

Chemistry

Vitamin K is a fat-soluble vitamin that is stable in air and moisture but decomposes in sunlight.

1,4-naphthoquinone, with a 3-phytyl substituent. It is found naturally in a wide variety of green plants, particularly in leaves, since it functions as an electron acceptor during photosynthesis, forming part of the electron transport chain of photosystem I.[15][16]

Biological function

Main article: vitamin K

Animals

The best-known function of vitamin K in animals is as a cofactor in the formation of

prothrombin
), VII, IX, and X by the liver. It is also required for the formation of anticoagulant factors protein C and S. Vitamin K is required for bone protein formation.

In terms of distribution, phylloquinone typically occurs in higher levels in the liver, heart and pancreas, but in lower levels in the brain, kidneys, and lungs.[17]

Plants and cyanobacteria

Vitamin K1 is required for plant photosynthesis, where it participates in the Photosystem I electron transport chain.[18]

Biosynthesis

The biosynthesis of vitamin K1 via the transformation of chorismate occurs in nine steps.

Vitamin K1 is synthesized from chorismate, a compound produced from shikimate via the shikimate pathway. The conversion of chorismate to vitamin K1 comprises a series of nine steps:[19][20][21]

  1. Chorismate is isomerized to isochorismate by isochorismate synthase, or MenF (menaquinone enzyme).
  2. Addition of 2-oxoglutarate to isochorismate by PHYLLO, a multifunctional protein comprising three different enzymatic activities (MenD, H, and C).
  3. Elimination of pyruvate by PHYLLO.
  4. Aromatization to yield o-succinyl benzoate by PHYLLO.
  5. O-succinylbenzoate activation to corresponding CoA ester by MenE.
  6. Naphthoate ring formation by naphthoate synthase (MenB/NS).
  7. Thiolytic release of CoA by a thioesterase (MenH).
  8. Attachment of phytol chain to the naphthoate ring (MenA/ABC4).
  9. Methylation of the precursor at position 3 (MenG).

References

  1. FDA
    . Retrieved 22 Oct 2023.
  2. ^ a b "Notice: Multiple additions to the Prescription Drug List (PDL) [2023-08-30]". Health Canada. 26 October 2023. Retrieved 3 January 2024.
  3. ^ a b https://pdf.hres.ca/dpd_pm/00071484.PDF
  4. ISBN 9780128005880. Archived
    from the original on 2016-12-30.
  5. ^ a b c d e f g h i j k "Phytonadione". The American Society of Health-System Pharmacists. Archived from the original on 29 December 2016. Retrieved 8 December 2016.
  6. hdl:10665/325771
    . WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  7. ^ Furman L (27 July 2018). "American Academy of Pediatrics on vitamin k in the newborn period".
  8. PMID 12392385
    .
  9. PMID 12769509
    .
  10. ^ "Phytonadione Use During Pregnancy". Drugs.com. Archived from the original on 29 December 2016. Retrieved 29 December 2016.
  11. ^ "Vitamin K". Office of Dietary Supplements. U.S. National Institutes of Health. 11 February 2016. Archived from the original on 31 December 2016. Retrieved 30 December 2016.
  12. ^
    ISBN 9780471899792. Archived
    from the original on 2016-12-30.
  13. PMID 7086539
    .
  14. ^ Institute of Medicine (US) Panel on Micronutrients. "Dietary Reference Intakes for Vitamin A, Vitamin K, Arsenic, Boron, Chromium, Copper, Iodine, Iron, Manganese, Molybdenum, Nickel, Silicon, Vanadium, and Zinc". Washington (DC): National Academies Press (US). Retrieved 25 November 2021 – via NCBI.
  15. S2CID 84602152
    .
  16. S2CID 42983611
    .
  17. PMID 34945687
    .
  18. PMID 27337968
    .
  19. PMID 23821151
    .
  20. PMID 19321747
    .
  21. ISBN 9780123858535
    .

External links

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