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Menadione

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Subject: Vitamin K, Menadiol, Beta-Tocopherol, 22-Dihydroergocalciferol, Alpha-Tocotrienol
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Menadione

Dangerous for the Environment (Nature) N|
Menadione[1]
Skeltal formula
Ball-and-stick model
Names
IUPAC name
2-Methylnaphthalene-1,4-dione
Other names
Menaphthone; Vitamin K3; β-Methyl-1,4-naphthoquinone; 2-Methyl-1,4-naphthodione; 2-Methyl-1,4-naphthoquinone
Identifiers
 YesY
ATC code B02
ChEBI  N
ChEMBL  YesY
ChemSpider  YesY
DrugBank  N
Jmol-3D images Image
KEGG  YesY
PubChem
UNII  YesY
Properties
small=yes}}} }}} 0}}} 1=C|C} }}} 1=H|H} }}} 1=Ac|Ac} }}} 1=Ag|Ag} }}} 1=Al|Al} }}} 1=Am|Am} }}} 1=Ar|Ar} }}} 1=As|As} }}} 1=At|At} }}} 1=Au|Au} }}} 1=B|B} }}} 1=Ba|Ba} }}} 1=Be|Be} }}} 1=Bh|Bh} }}} 1=Bi|Bi} }}} 1=Bk|Bk} }}} 1=Br|Br} }}} 1=Ca|Ca} }}} 1=Cd|Cd} }}} 1=Ce|Ce} }}} 1=Cf|Cf} }}} 1=Cn|Cn} }}} 1=Cl|Cl} }}} 1=Cm|Cm} }}} 1=Co|Co} }}} 1=Cr|Cr} }}} 1=Cs|Cs} }}} 1=Cu|Cu} }}} 1=Db|Db} }}} 1=Ds|Ds} }}} 1=Dy|Dy} }}} 1=Er|Er} }}} 1=Es|Es} }}} 1=Eu|Eu} }}} 1=F|F} }}} 1=Fe|Fe} }}} 1=Fl|Fl} }}} 1=Fm|Fm} }}} 1=Fr|Fr} }}} 1=Ga|Ga} }}} 1=Gd|Gd} }}} 1=Ge|Ge} }}} 1=He|He} }}O2}}
Documentation

Appearance Bright yellow crystals
Density 1.225g/cm3
Melting point 105 to 107 °C (221 to 225 °F; 378 to 380 K)
Boiling point 304.5 °C (580.1 °F; 577.7 K) @ 760mmHg
Insoluble
Hazards
Flash point 113.8 °C (236.8 °F; 387.0 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
0.5 g/kg (oral, mouse)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: YesY/N?)

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.[2]

Terminology

It is sometimes called vitamin K3,[3] although derivatives of naphthoquinone are not naturally occurring chemicals and therefore do not qualify as vitamins, and without the side chain in the 2-position they cannot exert all the functions of the K vitamins. Menadione is metabolized by the human body into K2 which uses alkylation to yield menaquinones (MK-n, n=1-13; K2 vitamers), hence is better classified as a provitamin.

It is also known as "menaphthone".[4]

Uses

Despite the fact that it can serve as a precursor to various types of vitamin K, 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. It is used in the treatment of hypoprothrombinemia outside of the United States.

Toxicity

Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to glucose-6-phosphate dehydrogenase 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 because of their potential toxicity in human use.

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. These doses have yielded no reported cases of toxicity from menadione in livestock or pets.

Experimental research

Recently, menadione in combination with vitamin C is being studied as a potential treatment for prostate cancer.[5][6]

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 kinases by drugs such as erlotinib (Tarceva) and cetuximab (Erbitux).[7][8]

References

  1. ^ The Merck Index, 11th Edition, 5714
  2. ^
  3. ^
  4. ^
  5. ^
  6. ^
  7. ^
  8. ^

External links

  • Menadione in the Pesticide Properties DataBase (PPDB)
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