Menatetrenone

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Menatetrenone
Menatetrenone.PNG
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 International Drug Names
Legal status
?
Routes Oral
Identifiers
CAS number 863-61-6 YesY
ATC code None
PubChem CID 5282367
ChemSpider 4445530
UNII 27Y876D139 YesY
KEGG D00100 YesY
ChEBI CHEBI:78277 YesY
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 
Mol. mass 444.648 g/mol
 YesY (what is this?)  (verify)

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[edit]

References[edit]

  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. doi:10.1111/j.1753-4887.2006.tb00184.x. PMID 17274493. 
  2. ^ Shearer, Shearer MJ; Newman P. (2008). "Metabolism and cell biology of vitamin K". Thrombosis and Haemostasis: 530–547. doi:10.1160/TH08-03-0147. 
  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. PMID 9446847. 
  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. doi:10.1016/S0304-4165(97)00089-5. PMID 9468334. 
  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. doi:10.1079/BJN19940043. PMID 7947656. 
  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. PMID 1453219. 
  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. PMID 9446847. 
  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. doi:10.1016/S0304-4165(97)00089-5. PMID 9468334. 

External links[edit]

  • Product information: "Glakay" (PDF). Eisai Co. November 2009. Retrieved 2012-01-10.