Clinical data | |
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Trade names | Mephyton, others |
Other names | Vitamin K1, phytonadione, phylloquinone, (E)-phytonadione |
AHFS/Drugs.com | Monograph |
Routes of administration | by mouth, subQ, IM, IV |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.001.422 |
Chemical and physical data | |
Formula | C31H46O2 |
Molar mass | 450.707 g·mol−1 |
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Phytomenadione, also known as vitamin K1 or phylloquinone, is a vitamin found in food and used as a dietary supplement. [1] [2] It is on the World Health Organization's List of Essential Medicines. [3]
As a supplement it is used to treat certain bleeding disorders. [2] This includes warfarin overdose, vitamin K deficiency, and obstructive jaundice. [2] It is also recommended to prevent and treat vitamin K deficiency bleeding in infants. [2] Use is typically recommended by mouth, intramuscular injection or injection under the skin. [2] When given by injection benefits are seen within two hours. [2] Many countries in the world choose intramuscular injections in newborn to keep them safe from severe bleeding (VKDB). It is considered a safe treatment and saves many children from death and severe neurologic deficit every year. [4]
Side effects when given by injection may include pain at the site of injection. [2] 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. [5] Use during pregnancy is considered safe, [6] use is also likely okay during breastfeeding. [7] It works by supplying a required component for making a number of blood clotting factors. [2] Food sources include green vegetables, vegetable oil, and some fruit. [8]
Phytomenadione was first isolated in 1939. [9] In 1943 Edward Doisy and Henrik Dam were given a Nobel Prize for its discovery. [9]
Phytomenadione is often also called phylloquinone, vitamin K, [10] or phytonadione.
A stereoisomer of phylloquinone is called vitamin k1 (note the difference in capitalization).[ citation needed ]
This section needs additional citations for verification .(July 2019) |
Vitamin K is a fat-soluble vitamin that is stable in air and moisture but decomposes in sunlight. [11] 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. [12] [13]
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.
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. [14]
Vitamin K1 is required for plant photosynthesis, where it participates in the Photosystem I electron transport chain. [15]
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: [16] [17] [18]
Vitamin C is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical "serum" ingredient to treat melasma and wrinkles on the face. It is used to prevent and treat scurvy. Vitamin C is an essential nutrient involved in the repair of tissue, the formation of collagen, and the enzymatic production of certain neurotransmitters. It is required for the functioning of several enzymes and is important for immune system function. It also functions as an antioxidant. Most animals are able to synthesize their own vitamin C. However, apes and monkeys, most bats, some rodents, and certain other animals must acquire it from dietary sources.
Vitamin K is a family of structurally similar, fat-soluble vitamers found in foods and marketed as dietary supplements. The human body requires vitamin K for post-synthesis modification of certain proteins that are required for blood coagulation or for controlling binding of calcium in bones and other tissues. The complete synthesis involves final modification of these so-called "Gla proteins" by the enzyme gamma-glutamyl carboxylase that uses vitamin K as a cofactor.
The quinones are a class of organic compounds that are formally "derived from aromatic compounds [such as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double bonds, resulting in "a fully conjugated cyclic dione structure". The archetypical member of the class is 1,4-benzoquinone or cyclohexadienedione, often called simply "quinone". Other important examples are 1,2-benzoquinone (ortho-quinone), 1,4-naphthoquinone and 9,10-anthraquinone.
Photosystem I is one of two photosystems in the photosynthetic light reactions of algae, plants, and cyanobacteria. Photosystem I is an integral membrane protein complex that uses light energy to catalyze the transfer of electrons across the thylakoid membrane from plastocyanin to ferredoxin. Ultimately, the electrons that are transferred by Photosystem I are used to produce the moderate-energy hydrogen carrier NADPH. The photon energy absorbed by Photosystem I also produces a proton-motive force that is used to generate ATP. PSI is composed of more than 110 cofactors, significantly more than Photosystem II.
Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for:
Menadione is a natural organic compound with the formula C6H4(CO)2C2H(CH3). It is an analog of 1,4-naphthoquinone with a methyl group in the 2-position. It is sometimes called vitamin K3. Use is allowed as a nutritional supplement in animal feed because of its vitamin K activity.
An aromatic amino acid is an amino acid that includes an aromatic ring.
Menatetrenone (INN), also known as menaquinone-4 (MK-4), is one of the nine forms of vitamin K2.
In enzymology, a NAD(P)H dehydrogenase (quinone) (EC 1.6.5.2) is an enzyme that catalyzes the chemical reaction
The enzyme 1,4-dihydroxy-2-naphthoyl-CoA synthase catalyzes the sixth step in the biosynthesis of phylloquinone and menaquinone, the two forms of vitamin K. In E. coli, 1,4-dihydroxy-2-naphthoyl-CoA synthase, formerly known as naphthoate synthase, is encoded by menB and uses O-succinylbenzoyl-CoA as a substrate and converts it to 1,4-dihydroxy-2-naphthoyl-CoA.
o-Succinylbenzoate—CoA ligase, encoded from the menE gene in Escherichia coli, catalyzes the fifth reaction in the synthesis of menaquinone. This pathway is called 1, 4-dihydroxy-2-naphthoate biosynthesis I. Vitamin K is a quinone that serves as an electron transporter during anaerobic respiration. This process of anaerobic respiration allows the bacteria to generate the energy required to survive.
The enzyme chorismate synthase catalyzes the chemical reaction
2-Succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase, also known as SHCHC synthase is encoded by the menH gene in Escherichia coli and functions in the synthesis of vitamin K. The specific step in the synthetic pathway that SHCHC synthase catalyzes is the conversion of 5-enolpyruvoyl-6-hydroxy-2-succinylcyclohex-3-ene-1-carboxylate to (1R,6R)-6-hydroxy-2-succinylcyclohexa-2,4-diene-1-carboxylate and pyruvate.
Vitamin K reactions are adverse side effects that may occur after injection with vitamin K. The liver utilizes vitamin K to produce coagulation factors that help the body form blood clots which prevent excessive bleeding. Vitamin K injections are administered to newborns as a preventative measure to reduce the risk of hemorrhagic disease of the newborn (HDN).
The shikimate pathway is a seven-step metabolic pathway used by bacteria, archaea, fungi, algae, some protozoans, and plants for the biosynthesis of folates and aromatic amino acids. This pathway is not found in animal cells.
Vitamin K2 or menaquinone (MK) is one of three types of vitamin K, the other two being vitamin K1 (phylloquinone) and K3 (menadione). K2 is both a tissue and bacterial product (derived from vitamin K1 in both cases) and is usually found in animal products or fermented foods.
1-4-dihydroxy-2-napthoate (DHNA) polyprenyltransferase (EC 2.5.1.74)is an enzyme that catalyzes the chemical reaction: all-trans-nonaprenyl diphosphate + 1-4-dihydroxy-2-napthoate + H+ demethylmenaquinol-9 + diphosphate + carbon dioxide
The enzyme 1,4-dihydroxy-2-naphthoyl-CoA hydrolase (EC 3.1.2.28; systematic name 1,4-dihydroxy-2-naphthoyl-CoA hydrolase) catalyses the following reaction:
Peptidyl-glutamate 4-carboxylase (EC 4.1.1.90, vitamin K-dependent carboxylase, gamma-glutamyl carboxylase) is an enzyme with systematic name peptidyl-glutamate 4-carboxylase (2-methyl-3-phytyl-1,4-naphthoquinone-epoxidizing). This enzyme catalyses the following chemical reaction
o-Succinylbenzoate synthase (OSBS) (EC 4.2.1.113) is an enzyme encoded by the menC gene in E.coli, and catalyzes the dehydration of 2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate (SHCHC) to form 4-(2'-carboxyphenyl)-4-oxobutyrate, also called o-succinylbenzoate or OSB, hence the name of the enzyme. This reaction is the fourth step in the menaquinone biosynthetic pathway, which is used by bacteria to synthesize menaquinone, also known as vitamin K2.