Phytomenadione

Phytomenadione
Clinical data
Trade names Mephyton, others
AHFS/Drugs.com Monograph
Pregnancy
category
  • US: C (Risk not ruled out)
Routes of
administration		 by mouth, subQ, IM, IV
ATC code
Identifiers
Synonyms Vitamin K1, phytonadione, phylloquinone
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard 100.001.422
Chemical and physical data
Formula C31H46O2
Molar mass 450.70 g/mol
3D model (JSmol)

Phytomenadione, also known as vitamin K1 or phylloquinone, is a vitamin found in food and used as a dietary supplement.[1][2] As a supplement it is used to treat certain bleeding disorders.[2] This includes in warfarin overdose, vitamin K deficiency, and obstructive jaundice.[2] It is also recommended to prevent and treat hemorrhagic disease of the newborn.[2] Use is typically recommended by mouth or injection under the skin.[2] Use by injection into a vein or muscle is recommended only when other routes are not possible.[2] When given by injection benefits are seen within two hours.[2]

Common side effects when given by injection include pain at the site of injection and altered taste.[2] Severe allergic reactions may occur with injected into a vein or muscle.[2] It is unclear if use during pregnancy is safe; however, use is likely okay during breastfeeding.[3] It works by supplying a required component for making a number of blood clotting factors.[2] Found sources include green vegetables, vegetable oil, and some fruit.[4]

Phytomenadione was first isolated in 1939.[5] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[6] The wholesale cost in the developing world is about 0.11 to 1.27 USD for a 10 mg vial.[7] In the United States a course of treatment costs less than 25 USD.[8] In 1943 Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery.[5]

Terminology

Phytomenadione is often called phylloquinone or vitamin K,[9] phytomenadione or phytonadione. Sometimes a distinction is made between phylloquinone, which is considered to be a natural substance, and phytonadione, which is considered to be a synthetic substance.[10]

A stereoisomer of phylloquinone is called vitamin k1 (note the difference in capitalization).

Chemistry

Vitamin K is a fat-soluble vitamin that is stable in air and moisture but decomposes in sunlight. It is a polycyclic aromatic ketone, based on 2-methyl-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.

Phylloquinone is an electron acceptor during photosynthesis, forming part of the electron transport chain of Photosystem I.

The best-known function of vitamin K in animals is as a cofactor in the formation of coagulation factors II (prothrombin), VII, IX, and X by the liver. It is also required for the formation of anticoagulant factors protein C and S. It is commonly used to treat warfarin toxicity, and as an antidote for coumatetralyl.

Vitamin K is required for bone protein formation.

See also

References

  1. ↑ Watson, Ronald Ross (2014). Diet and Exercise in Cystic Fibrosis. Academic Press. p. 187. ISBN 9780128005880.
  2. 1 2 3 4 5 6 7 8 9 10 "Phytonadione". The American Society of Health-System Pharmacists. Retrieved 8 December 2016.
  3. ↑ "Phytonadione Use During Pregnancy". Drugs.com. Retrieved 29 December 2016.
  4. ↑ "Office of Dietary Supplements – Vitamin K". ods.od.nih.gov. 11 February 2016. Retrieved 30 December 2016.
  5. 1 2 Sneader, Walter (2005). Drug Discovery: A History. John Wiley & Sons. p. 243. ISBN 9780471899792.
  6. ↑ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Retrieved 8 December 2016.
  7. ↑ "Vitamin K1". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  8. ↑ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 229. ISBN 9781284057560.
  9. ↑ Haroon, Y.; Shearer, M. J.; Rahim, S.; Gunn, W. G.; McEnery, G.; Barkhan, P. (June 1982). "The content of phylloquinone (vitamin K1) in human milk, cows' milk, and infant formula foods determined by high-performance liquid chromatography". J. Nutr. 112 (6): 1105–1117. PMID 7086539.
  10. ↑ "Vitamin K". Retrieved 2009-03-18.
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