Menatetrenone

Menatetrenone

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name 2-methyl-3-[(2Z,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]naphthoquinone
Synonyms	3-methyl-2-[(2Z,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione
CAS Number	863-61-6 Y
PubChem CID	5282367
ChemSpider	4445530 N
UNII	27Y876D139
KEGG	D00100 Y
ChEBI	CHEBI:78277 N
Chemical and physical data
Formula	C31H40O2
Molar mass	444.648 g/mol
3D model (JSmol)	Interactive image
SMILES CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C
InChI InChI=1S/C31H40O2/c1-22(2)12-9-13-23(3)14-10-15-24(4)16-11-17-25(5)20-21-27-26(6)30(32)28-18-7-8-19-29(28)31(27)33/h7-8,12,14,16,18-20H,9-11,13,15,17,21H2,1-6H3/b23-14+,24-16+,25-20+ N Key:DKHGMERMDICWDU-GHDNBGIDSA-N N
NY (what is this?)

Menatetrenone (INN), also known as MK-4, 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.

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

MK-4 is marketed for the osteoporosis indication in Japan by Eisai Co., under the trade name Glakay.