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Menatetrenone

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Title: Menatetrenone  
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Menatetrenone

Menatetrenone
Structural formula of menatetrenone
Space-filling model of the menatetrenone molecule
Systematic (IUPAC) name
2-methyl-3-[(2Z,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]naphthoquinone
Clinical data
AHFS/Drugs.com
Routes of
administration
Oral
Identifiers
CAS Registry Number  Y
ATC code None
PubChem CID:
ChemSpider  N
UNII  Y
KEGG  Y
ChEBI  N
Synonyms 3-methyl-2-[(2Z,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione
Chemical data
Formula C31H40O2
Molecular mass 444.648 g/mol
 N   

Menatetrenone (INN), also known as MK4, is a vitamin K compound used as a hemostatic agent, and also as adjunctive therapy for the pain of osteoporosis. Menatetrenone is one of the nine forms of vitamin K2.[1]

MK4 is produced via conversion of vitamin K1 in the body, in the testes, pancreas and arterial walls.[2] While major questions still surround the biochemical pathway for the transformation of vitamin K1 to MK4, studies demonstrate the conversion is not dependent on gut bacteria, occurring in germ-free rats[3][4] and in parenterally-administered K1 in rats.[5][6] In fact, tissues that accumulate high amounts of MK4 have a remarkable capacity to convert up to 90% of the available K1 into MK4.[7][8]

MK4 is marketed for the osteoporosis indication in Japan by Eisai Co., under the trade name Glakay.

See also

References

  1. ^ Iwamoto J, Takeda T, Sato Y (December 2006). "Menatetrenone (vitamin K2) and bone quality in the treatment of postmenopausal osteoporosis". Nutr. Rev. 64 (12): 509–17.  
  2. ^ Shearer, Shearer MJ; Newman P. (2008). "Metabolism and cell biology of vitamin K". Thrombosis and Haemostasis: 530–547.  
  3. ^ Davidson, RT; Foley AL; Engelke JA; Suttie JW (1998). "Conversion of Dietary Phylloquinone to Tissue Menaquinone-4 in Rats is Not Dependent on Gut Bacteria1". Journal of Nutrition 128 (2): 220–223.  
  4. ^ Ronden, JE; Drittij-Reijnders M-J, Vermeer C, Thijssen HHW. (1998). "Intestinal flora is not an intermediate in the phylloquinone-menaquinone-4 conversion in the rat". Biochimica et Biophysica Acta (BBA) - General Subjects 1379 (1): 69–75.  
  5. ^ Thijssen, HHW; Drittij-Reijnders MJ (1994). "Vitamin K distribution in rat tissues: dietary phylloquinone is a source of tissue menaquinone-4". British Journal of Nutrition 72 (3): 415–425.  
  6. ^ Will, BH; Usui Y; Suttie JW (1992). "Comparative Metabolism and Requirement of Vitamin K in Chicks and Rats". Journal of Nutrition 122 (12): 2354–2360.  
  7. ^ Davidson, RT; Foley AL; Engelke JA; Suttie JW (1998). "Conversion of Dietary Phylloquinone to Tissue Menaquinone-4 in Rats is Not Dependent on Gut Bacteria". Journal of Nutrition 128 (2): 220–223.  
  8. ^ Ronden, JE; Drittij-Reijnders M-J; Vermeer C; Thijssen HHW (1998). "Intestinal flora is not an intermediate in the phylloquinone-menaquinone-4 conversion in the rat". Biochimica et Biophysica Acta (BBA) - General Subjects 1379 (1): 69–75.  

External links

  • Product information: "Glakay" (PDF).  


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