Phytomenadione

Overview

Phytomenadione, also known as vitamin K₁, phylloquinone, or phytonadione, is a vitamin found in food and used as a dietary supplement. It is on the World Health Organization's List of Essential Medicines.[1][2][3] WP

It is used to treat certain bleeding disorders, including warfarin overdose, vitamin K deficiency, and obstructive jaundice. Use is typically recommended by mouth, intramuscular injection or injection under the skin. When given by injection benefits are seen within two hours. It is also recommended for preventing and treating vitamin K deficiency bleeding in infants. Many countries in the world choose intramuscular injections in newborn to keep them safe from vitamin K deficiency bleeding. It is considered a safe treatment and saves many children from death and severe neurologic deficit every year.[2][4] WP

Side effects when given by injection may include pain at the site of injection. 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. Use during pregnancy is considered safe, use is also likely okay during breastfeeding. It works by supplying a required component for making a number of blood clotting factors. Food sources include green vegetables, vegetable oil, and some fruit.[2][5–8] WP

Phytomenadione was first isolated in 1939. In 1943, Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery.[9] WP

Uses, dosage and effects

Medical uses

It is used to treat certain bleeding disorders, including warfarin overdose (also overdose of similar compounds such as coumatetralyl), vitamin K deficiency, and obstructive jaundice. It is used to prevent and treat vitamin K deficiency bleeding in infants.[2] WP

Veterinary uses

In Canada, phytomenadione (Hemophyt) is indicated for the treatment of anticoagulant poisoning in dogs.[10][11] WP

Toxicity

Chemistry

Formula

C31H46O2 PC

Molar mass (g/mol)

450.7 PC

IUPAC name (computed by PubChem)

2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione PC

SMILES

CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C PC

InChIKey

MBWXNTAXLNYFJB-NKFFZRIASA-N PC

PubChem CID

5284607

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Watson RR. Diet and Exercise in Cystic Fibrosis. 2014
2. Other Phytonadione
3. Other The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). 2023
4. Other Furman L. American Academy of Pediatrics on vitamin k in the newborn period. 27 July 2018
5. Journal / agency Riegert-Johnson DL, Volcheck GW. The incidence of anaphylaxis following intravenous phytonadione (vitamin K1): a 5-year retrospective review. Annals of Allergy, Asthma & Immunology. October 2002. doi:10.1016/S1081-1206(10)62042-X · PMID 12392385
6. Journal / agency Bailey B. 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. February 2003. doi:10.1002/bdra.10007 · PMID 12769509
7. Other Phytonadione Use During Pregnancy
8. Journal / agency Vitamin K. 11 February 2016
9. Other Sneader, Walter. Drug Discovery: A History. 2005
10. Other Notice: Multiple additions to the Prescription Drug List (PDL) [2023-08-30]. 26 October 2023
11. Other Hemophyt Monograph. February 24, 2023

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.