Menadione
Encyclopedia
Menadione is a synthetic chemical compound sometimes used as a nutritional supplement because of its vitamin K
activity. It is an analog of 1,4-naphthoquinone with a methyl group
in the 2-position.
It is also known as "menaphthone".
, menadione is generally not used as a nutritional supplement in economically developed countries. Menadione for human use at pharmaceutical strength is available in some countries with large lower income populations. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia
due to G6PD deficiency
, neonatal brain or liver damage, or neonatal death in some rare cases. In the United States, menadione supplements are banned by the U.S. Food and Drug Administration (FDA) because of their potential toxicity.
Low dose menadione is still used as an inexpensive micronutrient for livestock in many countries. Forms of menadione are also included in some pet foods in developed countries as a source of vitamin K.
It is used in the treatment of Hypoprothrombinemia
since 1947. More recently, menadione in combination with vitamin C
is being studied as a potential treatment for prostate cancer.
A menadione topical lotion was recently developed to reduce epidermal growth factor receptor
inhibitor related side effects, by the prevention of skin toxicities that result from inhibition
of protein kinase
s by drugs such as erlotinib
(Tarceva) and cetuximab
(Erbitux).
Vitamin K
Vitamin K is a group of structurally similar, fat soluble vitamins that are needed for the posttranslational modification of certain proteins required for blood coagulation and in metabolic pathways in bone and other tissue. They are 2-methyl-1,4-naphthoquinone derivatives...
activity. It is an analog of 1,4-naphthoquinone with a methyl group
Methyl group
Methyl group is a functional group derived from methane, containing one carbon atom bonded to three hydrogen atoms —CH3. The group is often abbreviated Me. Such hydrocarbon groups occur in many organic compounds. The methyl group can be found in three forms: anion, cation and radical. The anion...
in the 2-position.
Terminology
It is sometimes called vitamin K3, although derivatives of naphthoquinone without the side chain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K2 which utilizes alkylation to yield menaquinones (MK-n, n=1-13; K2 vitamers), and hence, is better classified as a provitamin.It is also known as "menaphthone".
Uses
Despite the fact that it can serve as a precursor to various types of vitamin KVitamin K
Vitamin K is a group of structurally similar, fat soluble vitamins that are needed for the posttranslational modification of certain proteins required for blood coagulation and in metabolic pathways in bone and other tissue. They are 2-methyl-1,4-naphthoquinone derivatives...
, menadione is generally not used as a nutritional supplement in economically developed countries. Menadione for human use at pharmaceutical strength is available in some countries with large lower income populations. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia
Hemolytic anemia
Hemolytic anemia is a form of anemia due to hemolysis, the abnormal breakdown of red blood cells , either in the blood vessels or elsewhere in the human body . It has numerous possible causes, ranging from relatively harmless to life-threatening...
due to G6PD deficiency
Glucose-6-phosphate dehydrogenase deficiency
Glucose-6-phosphate dehydrogenase deficiency is an X-linked recessive hereditary disease characterised by abnormally low levels of glucose-6-phosphate dehydrogenase , a metabolic enzyme involved in the pentose phosphate pathway, especially important in red blood cell metabolism. G6PD deficiency is...
, neonatal brain or liver damage, or neonatal death in some rare cases. In the United States, menadione supplements are banned by the U.S. Food and Drug Administration (FDA) because of their potential toxicity.
Low dose menadione is still used as an inexpensive micronutrient for livestock in many countries. Forms of menadione are also included in some pet foods in developed countries as a source of vitamin K.
It is used in the treatment of Hypoprothrombinemia
Hypoprothrombinemia
Hypoprothrombinemia is a blood disorder in which a deficiency of prothrombin results in impaired blood clotting, leading to an increased physiological risk for bleeding, especially in the gastrointestinal system, cranial vault, and superficial integumentary system.-Causes:Hypoprothrombinemia can...
Experimental research
Menadione has been used experimentally as a chemotherapic agent for cancerCancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
since 1947. More recently, menadione in combination with vitamin C
Vitamin C
Vitamin C or L-ascorbic acid or L-ascorbate is an essential nutrient for humans and certain other animal species. In living organisms ascorbate acts as an antioxidant by protecting the body against oxidative stress...
is being studied as a potential treatment for prostate cancer.
A menadione topical lotion was recently developed to reduce epidermal growth factor receptor
Epidermal growth factor receptor
The epidermal growth factor receptor is the cell-surface receptor for members of the epidermal growth factor family of extracellular protein ligands...
inhibitor related side effects, by the prevention of skin toxicities that result from inhibition
Enzyme inhibitor
An enzyme inhibitor is a molecule that binds to enzymes and decreases their activity. Since blocking an enzyme's activity can kill a pathogen or correct a metabolic imbalance, many drugs are enzyme inhibitors. They are also used as herbicides and pesticides...
of protein kinase
Protein kinase
A protein kinase is a kinase enzyme that modifies other proteins by chemically adding phosphate groups to them . Phosphorylation usually results in a functional change of the target protein by changing enzyme activity, cellular location, or association with other proteins...
s by drugs such as erlotinib
Erlotinib
Erlotinib hydrochloride is a drug used to treat non-small cell lung cancer, pancreatic cancer and several other types of cancer. It is a reversible tyrosine kinase inhibitor, which acts on the epidermal growth factor receptor . It is marketed in the United States by Genentech and OSI...
(Tarceva) and cetuximab
Cetuximab
Cetuximab is a chimeric monoclonal antibody, an epidermal growth factor receptor inhibitor, given by intravenous infusion for treatment of metastatic colorectal cancer and head and neck cancer.- Distribution :Cetuximab is manufactured and distributed in North America by ImClone and Bristol-Myers...
(Erbitux).