Phytomenadione, also known as vitamin K
1, phylloquinone, or phytonadione, is a
vitamin
Vitamins are Organic compound, organic molecules (or a set of closely related molecules called vitamer, vitamers) that are essential to an organism in small quantities for proper metabolism, metabolic function. Nutrient#Essential nutrients, ...
found in food and used as a
dietary supplement
A dietary supplement is a manufactured product intended to supplement a person's diet by taking a pill (pharmacy), pill, capsule (pharmacy), capsule, tablet (pharmacy), tablet, powder, or liquid. A supplement can provide nutrients eithe ...
.
[ It is on the ]World Health Organization's List of Essential Medicines
The WHO Model List of Essential Medicines (aka Essential Medicines List or EML), published by the World Health Organization (WHO), contains the medications considered to be most effective and safe to meet the most important needs in a health s ...
.
It is used to treat certain bleeding disorders
Coagulopathy (also called a bleeding disorder) is a condition in which the blood's ability to coagulate (form clots) is impaired. This condition can cause a tendency toward prolonged or excessive bleeding ( bleeding diathesis), which may occur s ...
,[ including warfarin overdose, vitamin K deficiency, and ]obstructive jaundice
Jaundice, also known as icterus, is a yellowish or, less frequently, greenish pigmentation of the skin and sclera due to high bilirubin levels. Jaundice in adults is typically a sign indicating the presence of underlying diseases involving ...
.[ 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.
Side effects when given by injection may include pain at the site of injection.][ Severe ]allergic reactions
Allergies, also known as allergic diseases, are various conditions caused by hypersensitivity of the immune system to typically harmless substances in the environment. These diseases include hay fever, food allergies, atopic dermatitis, alle ...
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
Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...
were given intravenously. Use during pregnancy is considered safe, use is also likely okay during breastfeeding
Breastfeeding, also known as nursing, is the process where breast milk is fed to a child. Infants may suck the milk directly from the breast, or milk may be extracted with a Breast pump, pump and then fed to the infant. The World Health Orga ...
. It works by supplying a required component for making a number of blood clotting factors
Coagulation, also known as clotting, is the process by which blood changes from a liquid to a gel, forming a blood clot. It results in hemostasis, the cessation of blood loss from a damaged vessel, followed by repair. The process of coagulation ...
.[ Food sources include green vegetables, vegetable oil, and some fruit.]
Phytomenadione was first isolated in 1939. In 1943 Edward Doisy and Henrik Dam
Carl Peter Henrik Dam (21 February 1895 – 17 April 1976) was a Danish biochemist and physiologist.
He was awarded the Nobel Prize in Medicine in 1943 for joint work with Edward Doisy in discovering vitamin K and its role in human physiolo ...
were given a Nobel Prize
The Nobel Prizes ( ; ; ) are awards administered by the Nobel Foundation and granted in accordance with the principle of "for the greatest benefit to humankind". The prizes were first awarded in 1901, marking the fifth anniversary of Alfred N ...
for its discovery.[
]
Terminology
Phytomenadione is often also called phylloquinone, vitamin K, or phytonadione.
Medical uses
It is used to treat certain bleeding disorders
Coagulopathy (also called a bleeding disorder) is a condition in which the blood's ability to coagulate (form clots) is impaired. This condition can cause a tendency toward prolonged or excessive bleeding ( bleeding diathesis), which may occur s ...
,[ including warfarin overdose (also overdose of similar compounds such as ]coumatetralyl
Coumatetralyl is an anticoagulant of the 4-hydroxycoumarin vitamin K antagonist type used as a rodenticide.
Common applications
Coumatetralyl is commonly used with grains and other cereals as a rodent poison in conjunction with a tracking powde ...
), vitamin K deficiency, and obstructive jaundice
Jaundice, also known as icterus, is a yellowish or, less frequently, greenish pigmentation of the skin and sclera due to high bilirubin levels. Jaundice in adults is typically a sign indicating the presence of underlying diseases involving ...
.[ It is used to prevent and treat vitamin K deficiency bleeding in infants.][
]
Chemistry
Vitamin K is a fat-soluble vitamin that is stable in air and moisture but decomposes in sunlight. K1 is a polycyclic aromatic
In organic chemistry, aromaticity is a chemical property describing the way in which a conjugated system, conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibits a stabilization stronger than would be expected from conjugati ...
ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
, based on 2-methyl
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...
-1,4-naphthoquinone
1,4-Naphthoquinone or para-naphthoquinone is a quinone derived from naphthalene. It forms volatile yellow triclinic crystals and has a sharp odor similar to benzoquinone. It is almost insoluble in cold water, slightly soluble in petroleum ethe ...
, with a 3-phytyl
Phytane is the isoprenoid alkane formed when phytol, a chemical substituent of chlorophyll, loses its hydroxyl group. When phytol loses one carbon atom, it yields pristane. Other sources of phytane and pristane have also been proposed than phyt ...
substituent
In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule.
The suffix ''-yl'' is used when naming organic compounds that contain a single bond r ...
. It is found naturally in a wide variety of green plants, particularly in leaves, since it functions as an electron acceptor during photosynthesis
Photosynthesis ( ) is a system of biological processes by which photosynthetic organisms, such as most plants, algae, and cyanobacteria, convert light energy, typically from sunlight, into the chemical energy necessary to fuel their metabo ...
, forming part of the electron transport chain of photosystem I
Photosystem I (PSI, or plastocyanin–ferredoxin oxidoreductase) is one of two photosystems in the Light-dependent reactions, photosynthetic light reactions of algae, plants, and cyanobacteria. Photosystem I is an integral membrane ...
.
Biological function
Animals
The best-known function of vitamin K in animals is as a cofactor in the formation of coagulation factor
Coagulation, also known as clotting, is the process by which blood changes from a liquid to a gel, forming a blood clot. It results in hemostasis, the cessation of blood loss from a damaged vessel, followed by repair. The process of coagulation ...
s II (prothrombin
Prothrombin (coagulation factor II) is encoded in the human by the F2-gene. It is proteolytically cleaved during the clotting process by the prothrombinase enzyme complex to form thrombin.
Thrombin (Factor IIa) (, fibrose, thrombase, throm ...
), 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.
Plants and cyanobacteria
Vitamin K1 is required for plant photosynthesis
Photosynthesis ( ) is a system of biological processes by which photosynthetic organisms, such as most plants, algae, and cyanobacteria, convert light energy, typically from sunlight, into the chemical energy necessary to fuel their metabo ...
, where it participates in the Photosystem I
Photosystem I (PSI, or plastocyanin–ferredoxin oxidoreductase) is one of two photosystems in the Light-dependent reactions, photosynthetic light reactions of algae, plants, and cyanobacteria. Photosystem I is an integral membrane ...
electron transport chain
An electron transport chain (ETC) is a series of protein complexes and other molecules which transfer electrons from electron donors to electron acceptors via redox reactions (both reduction and oxidation occurring simultaneously) and couples th ...
.
Biosynthesis
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:
# Chorismate is isomerized to isochorismate by isochorismate synthase, or MenF (menaquinone enzyme).
# Addition of 2-oxoglutarate to isochorismate by PHYLLO, a multifunctional protein comprising three different enzymatic activities (MenD, H, and C).
# Elimination of pyruvate by PHYLLO.
# Aromatization
Aromatization is a chemical reaction in which an aromaticity, aromatic system is formed from a single nonaromatic precursor. Typically aromatization is achieved by dehydrogenation of existing cyclic compounds, illustrated by the conversion of cycl ...
to yield o-succinyl benzoate by PHYLLO.
# O-succinylbenzoate activation to corresponding CoA ester by MenE.
# Naphthoate ring formation by naphthoate synthase (MenB/NS).
# Thiolytic release of CoA by a thioesterase (MenH).
# Attachment of phytol chain to the naphthoate ring (MenA/ABC4).
# Methylation
Methylation, in the chemistry, chemical sciences, is the addition of a methyl group on a substrate (chemistry), substrate, or the substitution of an atom (or group) by a methyl group. Methylation is a form of alkylation, with a methyl group replac ...
of the precursor at position 3 (MenG).
Veterinary uses
In Canada, phytomenadione (Hemophyt) is indicated
In medicine, an indication is a valid reason to use a certain test, medication, procedure, or surgery. There can be multiple indications to use a procedure or medication. An indication can commonly be confused with the term diagnosis. A diagnosis ...
for the treatment of anticoagulant poisoning in dogs.
References
External links
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{{Authority control
1,4-Naphthoquinones
Dog medications
Meroterpenoids
Veterinary medicine
Vitamers
Vitamin K
World Health Organization essential medicines
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