Phytomenadione

Phytomenadione
Clinical data
Trade namesMephyton, Hemophyt, others
Other namesVitamin K1, phytonadione, phylloquinone, (E)-phytonadione
AHFS/Drugs.comMonograph
Routes of
administration		By mouth, subcutaneous, intramuscular, 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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.422 Edit this at Wikidata
Chemical and physical data
FormulaC31H46O2
Molar mass450.707 g·mol−1
3D model (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 bleeding disorders,[5] including warfarin overdose, vitamin K deficiency, and obstructive jaundice.[5] Use is typically recommended by mouth, intramuscular injection or 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.[5] Severe allergic reactions may occur when it is injected into a vein or muscle, but this has mainly happened when large doses of a certain type of supplement containing castor oil were given intravenously.[8] Use during pregnancy is considered safe,[9] use is also likely okay during breastfeeding.[10] It works by supplying a required component for making a number of blood clotting factors.[5] Food sources include green vegetables, vegetable oil, and some fruit.[11]

Phytomenadione was first isolated in 1939.[12] In 1943 Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery.[12]

  1. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  2. ^ "Notice: Multiple additions to the Prescription Drug List (PDL) [2023-08-30]". Health Canada. 26 October 2023. Retrieved 3 January 2024.
  3. ^ https://pdf.hres.ca/dpd_pm/00071484.PDF [bare URL PDF]
  4. ^ Watson RR (2014). Diet and Exercise in Cystic Fibrosis. Academic Press. p. 187. ISBN 9780128005880. Archived from the original on 2016-12-30.
  5. ^ a b c d e f g h "Phytonadione". The American Society of Health-System Pharmacists. Archived from the original on 29 December 2016. Retrieved 8 December 2016.
  6. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. 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. ^ Riegert-Johnson DL, Volcheck GW (October 2002). "The incidence of anaphylaxis following intravenous phytonadione (vitamin K1): a 5-year retrospective review". Annals of Allergy, Asthma & Immunology. 89 (4): 400–406. doi:10.1016/S1081-1206(10)62042-X. PMID 12392385.
  9. ^ Bailey B (February 2003). "Are there teratogenic risks associated with antidotes used in the acute management of poisoned pregnant women?". Birth Defects Research. Part A, Clinical and Molecular Teratology. 67 (2): 133–140. doi:10.1002/bdra.10007. 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. ^ a b Sneader W (2005). Drug Discovery: A History. John Wiley & Sons. p. 243. ISBN 9780471899792. Archived from the original on 2016-12-30.