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Menadione

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.338 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3 checkY
    Key: MJVAVZPDRWSRRC-UHFFFAOYSA-N checkY
  • InChI=1/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
    Key: MJVAVZPDRWSRRC-UHFFFAOYAY
  • O=C\2c1c(cccc1)C(=O)/C(=C/2)C
Properties
C11H8O2
Molar mass 172.183 g·mol−1
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; 577.6 K) @ 760mmHg
Insoluble
Pharmacology
B02BA02 (WHO)
Hazards
Flash point 113.8 °C (236.8 °F; 386.9 K)
Lethal dose or concentration (LD, LC):
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 verify (what is checkY☒N ?)

Menadione is an 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.[2] It is occasionally used as a nutritional supplement because of its vitamin K activity.

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

It is an intermediate in the chemical synthesis of vitamin K by first reduction to the diol menadiol, which is suscepible to coupling to the phytol.[5]

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.[citation needed] It is used in the treatment of hypoprothrombinemia outside of the United States.

The menadione core is apparent in the structure of vitamin K.

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.

Research

Menadione in combination with vitamin C has been investigated for the treatment for prostate cancer.[6][7]

A menadione topical lotion reduces 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).[8][9]

References

  1. ^ The Merck Index, 11th Edition, 5714
  2. ^ Castro FA, Mariani D, Panek AD, Eleutherio EC, Pereira MD (2008). Fox, Debbie (ed.). "Cytotoxicity Mechanism of Two Naphthoquinones (Menadione and Plumbagin) in Saccharomyces cerevisiae". PLoS ONE. 3 (12): e3999. doi:10.1371/journal.pone.0003999. PMC 2600608. PMID 19098979.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: unflagged free DOI (link)
  3. ^ Scott GK, Atsriku C, Kaminker P, et al. (September 2005). "Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation". Mol. Pharmacol. 68 (3): 606–15. doi:10.1124/mol.105.013474. PMID 15939799.
  4. ^ "Vitamin K". Retrieved 2009-03-18.
  5. ^ Fritz Weber, August Rüttimann "Vitamin K" Ullmann's Encyclopedia Of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.o27_o08
  6. ^ James M. Jamison, Jacques Gilloteaux, Henryk S. Taper and Jack L. Summers (2001). "Evaluation of the In Vitro and In Vivo Antitumor Activities of Vitamin C and K-3 Combinations against Human Prostate Cancer" (PDF). J. Nutr. 131 (1): 158S–160S. PMID 11208954.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Tareen B, Summers JL, Jamison JM, Neal DR, McGuire K, Gerson L, Diokno A (2008). "A 12 Week, Open Label, Phase I/IIa Study Using Apatone® for the Treatment of Prostate Cancer Patients Who Have Failed Standard Therapy". Int J Med Sci. 5 (2): 62–67. doi:10.7150/ijms.5.62. PMC 2288789. PMID 18392145.
  8. ^ R. Perez-Soler; Y. Ling; Y. Zou; S.R. Deitcher (2008). "Local Rescue of Skin Toxicities Secondary to Kinase Inhibitor (KI) Therapy with Topical Menadione" (PDF). Annals of Oncology. doi:10.1093/annonc/mdn346.
  9. ^ Tianhong Li; Roman Perez-Soler (2009). "Skin toxicities associated with epidermal growth factor receptor inhibitors". Targeted Oncology. 4 (2): 107–119. doi:10.1007/s11523-009-0114-0. PMID 19452131. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
  • Menadione in the Pesticide Properties DataBase (PPDB)
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