Menatetrenone

Top

Home > Library > Miscellaneous > Wikipedia

Menatetrenone

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
Pregnancy cat.	?
Legal status	?
Routes	Oral
Identifiers
CAS number	863-61-6
ATC code	None
PubChem	CID 5282367
UNII	27Y876D139^Y
KEGG	D00100^Y
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
Y (what is this?) (verify)

Menatetrenone (INN), also known as MK4, is a menaquinone compound used as a hemostatic agent and as adjunctive therapy for the pain of osteoporosis. It is marketed for the latter indication in Japan by Eisai Co., under the trade name Glakay.

Menatetrenone (MK4) 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]

References

^ 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. http://openurl.ingenta.com/content/nlm?genre=article&issn=0029-6643&volume=64&issue=12&spage=509&aulast=Iwamoto.
^ Sell, DR; Monnier VM (1990). "End-stage renal disease and diabetes catalyze the formation of a pentose-derived crosslink from aging human collagen". Journal of Clinical Investigation 85 (2): 380–384. doi:10.1172/JCI114449. PMC 296435. PMID 2298912. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=296435.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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

Product information: "Glakay" (PDF). Eisai Co.. November 2009. http://www.eisai.jp/medical/products/di/EPI/GLA_SC_EPI.pdf. Retrieved 2012-01-10.

Vitamins (A11)

Fat soluble

A	α-Carotene · β-Carotene · Retinol^# · Tretinoin

D	D₂ (Ergosterol, Ergocalciferol^#) · D₃ (7-Dehydrocholesterol, Previtamin D₃, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol), Calcitroic acid) · D₄ (Dihydroergocalciferol) · D₅ · D analogues (Alfacalcidol, Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)

E	Tocopherol (Alpha, Beta, Gamma, Delta) · Tocotrienol (Alpha, Beta, Gamma, Delta) · Tocofersolan

K	Naphthoquinone · Phylloquinone (K₁) · Menatetrenone (K₂) · Menadione (K₃) · Menadiol (K₄)

Water soluble

B	B₁ (Thiamine^#) · B₂ (Riboflavin^#) · B₃ (Niacin, Nicotinamide^#) · B₅ (Pantothenic acid, Dexpanthenol, Pantethine) · B₆ (Pyridoxine^#, Pyridoxal phosphate, Pyridoxamine) · B₇ (Biotin) · B₉ (Folic acid, Dihydrofolic acid, Folinic acid) · B₁₂ (Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline

C	Ascorbic acid^# · Dehydroascorbic acid

Combinations

Multivitamins

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: NUT

cof, enz, met

noco, nuvi, sysi/epon, met

drug(A8/11/12)

This drug article relating to the gastrointestinal system is a stub. You can help Wikipedia by expanding it.

This entry is from Wikipedia, the leading user-contributed encyclopedia. It may not have been reviewed by professional editors (see full disclaimer)

Donate to Wikimedia

Post a question - any question - to the WikiAnswers community:

Copyrights:

Cite

Wikipedia on Answers.com This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article Menatetrenone. Read