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Chemical Compound Review

Glakay     3-methyl-2-[(2E,6E,10E)- 3,7,11,15...

Synonyms: Kaytwo, Menatetrenona, menatetrenone, Menatetrenonum, Menaquinone-4, ...
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Disease relevance of Vitamin K3


High impact information on Vitamin K3


Chemical compound and disease context of Vitamin K3


Biological context of Vitamin K3


Anatomical context of Vitamin K3


Associations of Vitamin K3 with other chemical compounds


Gene context of Vitamin K3


Analytical, diagnostic and therapeutic context of Vitamin K3

  • When tumors were induced in ICR/Ha female mice by the intraperitoneal injection of benzo(a)pyrene, those mice given vitamin K3 before or both before and after benzo(a)pyrene had a slower rate of tumor appearance and tumor death rate as compared with those receiving benzo(a)pyrene alone [1].
  • Transfusion of 120 ml of frozen fresh plasma led to an immediate increase in the procoagulant activities of vitamin K dependent protein, similar to that found after perfusion of plasma plus vitamin K3 [33].
  • A high-performance liquid chromatographic (HPLC) method for the determination of menadione sodium bisulphite (vitamin K3) in animal feed and premixes is described [34].
  • High-performance liquid chromatography of menaquinone-4, 2,3-epoxymenaquinone-4, demethylmenaquinone-4 and related compounds [35].
  • These factors and their possible effects on the potentiation of ADR cytotoxicity and the therapeutic significance of utilizing vitamin K3 as an adjuvant in the chemotherapy of MDR tumors is discussed [36].


  1. Vitamin K as a regulator of benzo(a)pyrene metabolism, mutagenesis, and carcinogenesis. Studies with rat microsomes and tumorigenesis in mice. Israels, L.G., Walls, G.A., Ollmann, D.J., Friesen, E., Israels, E.D. J. Clin. Invest. (1983) [Pubmed]
  2. Modulation of cytotoxicity of menadione sodium bisulfite versus leukemia L1210 by the acid-soluble thiol pool. Akman, S.A., Dietrich, M., Chlebowski, R., Limberg, P., Block, J.B. Cancer Res. (1985) [Pubmed]
  3. Modulation of arterial thrombosis tendency in rats by vitamin K and its side chains. Ronden, J.E., Groenen-van Dooren, M.M., Hornstra, G., Vermeer, C. Atherosclerosis (1997) [Pubmed]
  4. Vitamin K3 inhibits growth of human hepatoma HepG2 cells by decreasing activities of both p34cdc2 kinase and phosphatase. Juan, C.C., Wu, F.Y. Biochem. Biophys. Res. Commun. (1993) [Pubmed]
  5. Microscopic aspects of autoschizic cell death in human ovarian carcinoma (2774) cells following vitamin C, vitamin K3 or vitamin C:K3 treatment. Gilloteaux, J., Jamison, J.M., Arnold, D., Taper, H.S., Von Gruenigen, V.E., Summers, J.L. Microsc. Microanal. (2003) [Pubmed]
  6. The growth inhibitory effects of vitamins K and their actions on gene expression. Wang, Z., Wang, M., Finn, F., Carr, B.I. Hepatology (1995) [Pubmed]
  7. Treatment of mitochondrial myopathy due to complex III deficiency with vitamins K3 and C: A 31P-NMR follow-up study. Argov, Z., Bank, W.J., Maris, J., Eleff, S., Kennaway, N.G., Olson, R.E., Chance, B. Ann. Neurol. (1986) [Pubmed]
  8. Vitamin K3 (menadione) and related quinones, like tumor-promoting phorbol esters, alter the affinity of epidermal growth factor for its membrane receptors. Shoyab, M., Todaro, G.J. J. Biol. Chem. (1980) [Pubmed]
  9. Vitamin K3-induced cell cycle arrest and apoptotic cell death are accompanied by altered expression of c-fos and c-myc in nasopharyngeal carcinoma cells. Wu, F.Y., Chang, N.T., Chen, W.J., Juan, C.C. Oncogene (1993) [Pubmed]
  10. Vitamin K3-induced renal toxicosis in the horse. Rebhun, W.C., Tennant, B.C., Dill, S.G., King, J.M. J. Am. Vet. Med. Assoc. (1984) [Pubmed]
  11. The dose-dependent effect of BHT (butylated hydroxytoluene) on vitamin K-dependent blood coagulation in rats. Cottrell, S., Andrews, C.M., Clayton, D., Powell, C.J. Food Chem. Toxicol. (1994) [Pubmed]
  12. Comparison of vitamins K1, K2 and K3 effects on growth of rat glioma and human glioblastoma multiforme cells in vitro. Oztopçu, P., Kabadere, S., Mercangoz, A., Uyar, R. Acta neurologica Belgica. (2004) [Pubmed]
  13. Circulating levels of vitamin K1, menaquinone-4, and menaquinone-7 in healthy elderly Japanese women and patients with vertebral fractures and patients with hip fractures. Kawana, K., Takahashi, M., Hoshino, H., Kushida, K. Endocr. Res. (2001) [Pubmed]
  14. Antiproliferative effects of mitoxantrone in ADR-sensitive and ADR-resistant P388 leukemia cells enhanced by vitamin K3. Parekh, H., Chavan, S., Chitnis, M. Tumori. (1991) [Pubmed]
  15. Vitamin K3 (menadione)-induced oncosis associated with keratin 8 phosphorylation and histone H3 arylation. Scott, G.K., Atsriku, C., Kaminker, P., Held, J., Gibson, B., Baldwin, M.A., Benz, C.C. Mol. Pharmacol. (2005) [Pubmed]
  16. Method for the determination of vitamin K homologues in human plasma using high-performance liquid chromatography-tandem mass spectrometry. Suhara, Y., Kamao, M., Tsugawa, N., Okano, T. Anal. Chem. (2005) [Pubmed]
  17. The relative effects of phylloquinone and menaquinone-4 on the blood coagulation factor synthesis in vitamin K-deficient rats. Groenen-van Dooren, M.M., Soute, B.A., Jie, K.S., Thijssen, H.H., Vermeer, C. Biochem. Pharmacol. (1993) [Pubmed]
  18. Reduction by inhibitors of mono(ADP-ribosyl)transferase of chemotaxis in human neutrophil leucocytes by inhibition of the assembly of filamentous actin. Allport, J.R., Donnelly, L.E., Hayes, B.P., Murray, S., Rendell, N.B., Ray, K.P., MacDermot, J. Br. J. Pharmacol. (1996) [Pubmed]
  19. Vitamin K3 induces cell cycle arrest and cell death by inhibiting Cdc25 phosphatase. Wu, F.Y., Sun, T.P. Eur. J. Cancer (1999) [Pubmed]
  20. UVA1 radiation triggers two different final apoptotic pathways. Godar, D.E. J. Invest. Dermatol. (1999) [Pubmed]
  21. 1,25-Dihydroxyvitamin D3 promotes vitamin K2 metabolism in human osteoblasts. Miyake, N., Hoshi, K., Sano, Y., Kikuchi, K., Tadano, K., Koshihara, Y. Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA. (2001) [Pubmed]
  22. The influence of oxygen free radicals on the permeability of the monolayer of cultured brain endothelial cells. Imaizumi, S., Kondo, T., Deli, M.A., Gobbel, G., Joó, F., Epstein, C.J., Yoshimoto, T., Chan, P.H. Neurochem. Int. (1996) [Pubmed]
  23. Vitamin K3 preferentially inhibits stimulation of phospholipase D-mediated hydrolysis of phosphatidylethanolamine by protein kinase C activators in NIH 3T3 fibroblasts. Tomono, M., Kiss, Z. Arch. Biochem. Biophys. (1994) [Pubmed]
  24. The formation of menaquinone-4 (vitamin K) and its oxide in some marine invertebrates. Burt, V.T., Bee, E., Pennock, J.F. Biochem. J. (1977) [Pubmed]
  25. Vitamins C and k3 sensitize human urothelial tumors to gemcitabine. Kassouf, W., Highshaw, R., Nelkin, G.M., Dinney, C.P., Kamat, A.M. J. Urol. (2006) [Pubmed]
  26. A study of factors which determine the pharmacological response to vitamin K in coumarin anticoagulated rabbits. Hart, J.A., Haynes, B.P., Park, B.K. Biochem. Pharmacol. (1984) [Pubmed]
  27. A transplasma membrane redox system in Phycomyces blakesleeanus: properties of a ferricyanide reductase activity regulated by iron level and vitamin K3. Baroja-Mazo, A., Del Valle, P., Rúa, J., Busto, F., De Cima, S., De Arriaga, D. J. Bioenerg. Biomembr. (2004) [Pubmed]
  28. Inhibition studies on chicken muscle aldose reductase. Murphy, D.G., Davidson, W.S. Biochem. Pharmacol. (1985) [Pubmed]
  29. H32, a Non-Quinone Sulfone Analog of Vitamin K3, Inhibits Human Hepatoma Cell Growth by Inhibiting Cdc25 and Activating ERK. Kar, S., Wang, M., Ham, S.W., Carr, B.I. Cancer Biol. Ther. (2006) [Pubmed]
  30. Induction of cytochrome P450 1A1 gene expression by a vitamin K3 analog in mouse hepatoma Hepa-1c1c7 cells. Chun, Y.J., Lee, B.Y., Yang, S.A., Ryu, C.K., Kim, M.Y. Mol. Cells (2001) [Pubmed]
  31. New approach to cancer therapy: the application of signal transduction to anti-cancer drug. Osada, S., Saji, S. Current medicinal chemistry. Anti-cancer agents. (2003) [Pubmed]
  32. Menadione (vitamin K3) enhances the mitogenic signal of epidermal growth factor via extracellular signal-regulated kinases. Markovits, J., Sun, T.P., Juan, C.C., Ju, G.C., Wu, F.Y. Int. J. Oncol. (1998) [Pubmed]
  33. Congenital deficiency of vitamin K-dependent coagulation factors and protein C. Vicente, V., Maia, R., Alberca, I., Tamagnini, G.P., Lopez Borrasca, A. Thromb. Haemost. (1984) [Pubmed]
  34. Fluorimetric determination of menadione sodium bisulphite (vitamin K3) in animal feed and premixes by high-performance liquid chromatography with post-column derivatization. Speek, A.J., Schrijver, J., Schreurs, W.H. J. Chromatogr. (1984) [Pubmed]
  35. High-performance liquid chromatography of menaquinone-4, 2,3-epoxymenaquinone-4, demethylmenaquinone-4 and related compounds. Donnahey, P.L., Burt, V.T., Rees, H.H., Pennock, J.F. J. Chromatogr. (1979) [Pubmed]
  36. Circumvention of adriamycin resistance: effect of 2-methyl-1,4-naphthoquinone (vitamin K3) on drug cytotoxicity in sensitive and MDR P388 leukemia cells. Parekh, H.K., Mansuri-Torshizi, H., Srivastava, T.S., Chitnis, M.P. Cancer Lett. (1992) [Pubmed]
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