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Vitamin K 3 (Menadione)

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A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo.

Also Known As:

Menadione; 2-Methyl-1,4-naphthalenedione; 2-Methyl-1,4-naphthoquinone; 2-Methylnaphthoquinone; Menadione Bisulfite; Menadione Sodium Bisulfite; Menadione Sodium Bisulfite, Trihydrate; Vicasol; Vikasol; Vitamin K3; Vitamin K3 Sodium Bisulfite; Bisulfite, Menadione; Bisulfite, Menadione Sodium; Sodium Bisulfite, Menadione

Networked: 405 relevant articles (17 outcomes, 41 trials/studies)

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Drug Context: Research Results

Experts

1.	Summers, Jack L: 12 articles (10/2014 - 05/2002)
2.	Jamison, James M: 12 articles (10/2014 - 05/2002)
3.	Gilloteaux, Jacques: 11 articles (10/2014 - 05/2002)
4.	Verrax, Julien: 9 articles (12/2011 - 05/2003)
5.	Calderon, Pedro Buc: 9 articles (12/2011 - 05/2002)
6.	Wakabayashi, Takashi: 8 articles (02/2007 - 01/2002)
7.	Kedzior, Jakub: 7 articles (02/2007 - 01/2002)
8.	Neal, Deborah R: 6 articles (05/2010 - 01/2004)
9.	Taper, Henryk S: 6 articles (09/2008 - 05/2002)
10.	Osada, Shinji: 5 articles (10/2015 - 03/2003)

Related Diseases

1.	Vitamin K Deficiency 08/01/2003 - "Development of vitamin K deficiency, measured as reduced blood-clotting capacity, took place in 43% of the Danish resistant rats and was independent of sex, treatment with supplementary vitamin K3 and sampling locality. " 11/01/2007 - "Comparable PIVKAII detection rate and PIVKAII levels in neonates receiving phytomenadione or menadione indicate their similar efficacy in prevention of vitamin K deficiency. " 08/01/1995 - "Hence, vitamin K prophylaxis is required for all newborns at birth and injectable vitamin K (menadione sodium bisulphite) given orally to term healthy babies is effective in preventing vitamin K deficiency state." 11/01/2007 - "To compare efficacy of intramuscular phytomenadione (fat soluble vitamin K or vitamin K1) with menadione (water soluble vitamin K or vitamin K3) in prevention of subclinical vitamin K deficiency. " 05/01/1983 - "That vitamin K1 enhances the benzo(a)pyrene effect while warfarin and vitamin K deficiency inhibit benzo(a)pyrene tumorigenesis indicates that vitamin K1, vitamin K deprivation, or possibly blockade of its metabolic cycle also modulates benzo(a)pyrene metabolism in vivo but by a mechanism or at a site different from the vitamin K3 effect. "
2.	Neoplasms (Cancer) 01/01/2011 - "A previous study in our laboratory showed that pre-exposure to ELF MF altered cancer-relevant cellular responses (cell cycle arrest, apoptosis) to menadione-induced DNA damage, but it did not include endpoints measuring actual genetic damage. " 03/27/2008 - "In this study, we address this gap by defining a new class of naphthoquinone-based IDO inhibitors exemplified by the natural product menadione, which is shown in mouse tumor models to have similar antitumor activity to previously characterized IDO inhibitors. " 06/01/2005 - "Based on the activity of menadione (M) in the human tumor stem cell assay, we conducted a phase I trial of M in patients with advanced cancer. " 12/01/2015 - "Menadione shows cytotoxic activity thought affecting redox cycling in cancer cells. " 01/01/2015 - "Vitamin K3 (vitK3) is a synthetic naphthoquinone exhibiting significant in vitro and in vivo anticancer activity against multiple human cancers, and has therapeutic potential when combined with other anticancer molecules. "
3.	Shock 09/01/2008 - "Significantly higher survival rates were obtained in Escherichia coli YB overexpressing AZR than in the control strain when treated by heat shock and oxidative stressors such as H(2)O(2) and menadione." 01/01/2006 - "However, shifting strains carrying temperature-sensitive alleles of SUG1 and SUG2 to the restrictive temperature strongly inhibited the expression of HSP26, HSP104 and GAD1 in response to heat shock or treatment with menadione bisulfate. " 04/01/2004 - "The behavior of the 10 menadione-sensitive mutants exposed to heat shock was investigated. " 08/01/2003 - "The expression of these genes induced by cell treatment with H2O2, but not menadione or 4NQO, was shown to decrease selectively after exposure to heat shock. " 05/15/2003 - "When exposed to treatments resulting in the generation of reactive oxygen species (ROS), including H(2)O(2), menadione, or heat shock, wild-type yeast died and exhibited apoptotic-like characteristics, consistent with previous studies. "
4.	Necrosis 02/05/1999 - "In the present study the HepG2 cell line was used for a comparative study of CD95-mediated apoptosis and menadione-induced necrosis. " 04/01/2015 - "The effect of tumour necrosis factor-α (TNF-α) ± interleukin-17C (IL-17C), without and with vitamin K3, was studied on BD-2 expression in epithelial SCC-25 cells. " 09/30/2003 - "At a 160 micro M dosage, menadione induced cell necrosis. " 09/30/2003 - "Menadione at dose of 80 micro M induced both apoptosis and necrosis. " 01/01/2003 - "Lack of apoptotic bodies, judged by flow cytometric analysis on sub-G1 nuclei and by electron microscopy in menadione-treated cells, suggested that the transition of cell death mode from apoptosis to necrosis occurred before the apoptotic processes were completed. "
5.	Thrombosis (Thrombus) 09/01/2006 - "The aim of this study was to assess the clinical efficacy of high dose vitamin K3 in the treatment of advanced HCC with portal vein thrombosis. " 09/01/2006 - "Forty-two consecutive patients with advanced HCC (Stage C according to BCLC staging system) with portal vein thrombosis were randomized into two groups: (i) high dose vitamin K3 (n = 23); and (ii) placebo (n = 19). "

Related Drugs and Biologics

1.	Vitamin K 3 (Menadione)
2.	Vitamin K
3.	Ascorbic Acid (Vitamin C)
4.	Hydrogen Peroxide (Hydroperoxide)
5.	Vitamin K 1 (Phylloquinone)
6.	Superoxides (Superoxide)
7.	Sodium
8.	Ethanol (Ethyl Alcohol)
9.	Vitamin K 2 (Vitamin K2)
10.	Mefloquine (Lariam)

Related Therapies and Procedures

1.	Drug Therapy (Chemotherapy)
2.	Aftercare (After-Treatment)
3.	Acupuncture Points (Acupuncture Point)
4.	Injections
5.	Intravenous Infusions