Details
Stereochemistry | ACHIRAL |
Molecular Formula | C31H40O2 |
Molecular Weight | 444.6481 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 3 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O
InChI
InChIKey=DKHGMERMDICWDU-GHDNBGIDSA-N
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+
Molecular Formula | C31H40O2 |
Molecular Weight | 444.6481 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 3 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/8511981
Curator's Comment: description was created based on several sources, including
http://www.ncbi.nlm.nih.gov/pubmed/8511981
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. MK4 is marketed for the osteoporosis indication in Japan by Eisai Co., under the trade name Glakay. Has several mechanism of actions: (1) Acceleration of osteogenesis. In human osteoblast cultures, calcification was accelerated by administration of menatetrenone at a concentration of 2.25 × 10-6 mol/L alone or when it was coadministered with 1,25(OH)2D3. The osteocalcin content in the cell layers was increased by coadministration with 1,25(OH)2D3. 2. Inhibition of bone resorption. In organ cultures of mouse calvaria, at concentrations of 3 × 10-6 to 3 × 10-5 mol/L, menatetrenone inhibited bone resorption induced by IL-1α, PGE2, PTH and 1,25(OH)2D3. In mouse bone marrow cell cultures, at concentrations of 3 × 10-6 to 1 × 10-5 mol/L, menatetrenone inhibited the induction of osteoclast release by 1,25(OH)2D3. 3. Effect on serum level of osteocalcin. Menatetrenone was administered to patients with osteoporosis at a dose of 45 mg/day for 2 years. Menatetrenone increased the serum level of osteocalcin and decreased the serum level of Glu-osteocalcin.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Acceleration of osteogenesis |
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Target ID: GO:0045453 |
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Target ID: serum level of osteocalcin |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Glakay Approved UseImprovement of decrease in bone mass and relief of pain in patients with osteoporosis Launch Date2004 |
PubMed
Title | Date | PubMed |
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Vitamin K(2) inhibits adipogenesis, osteoclastogenesis, and ODF/RANK ligand expression in murine bone marrow cell cultures. | 2000 Dec |
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Quinones as antimycobacterial agents. | 2004 Sep 15 |
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Identification of UBIAD1 as a novel human menaquinone-4 biosynthetic enzyme. | 2010 Nov 4 |
Sample Use Guides
The usual adult dosage for oral use is 45 mg of menatetrenone daily in three divided doses after meals.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/8511981
Menatetrenone (3 x 10(-6)-3 x 10(-5) M) inhibited the bone resorption induced by IL-1 alpha (2 U/ml), PGE2 (10(-7) M), PTH (3 x 10(-7) M), and 1,25-(OH)2D3 (3 x 10(-10) M) in a dose-dependent manner. Menatetrenone also inhibited the PGE2 production stimulated by IL-1 alpha. These results indicate that menatetrenone may inhibit bone resorption through at least two different mechanisms; one possibly is an inhibitory effect on prostaglandin production.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:23:28 GMT 2023
by
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on
Fri Dec 15 16:23:28 GMT 2023
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Record UNII |
27Y876D139
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C26017
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FDA ORPHAN DRUG |
319110
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FDA ORPHAN DRUG |
348111
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FDA ORPHAN DRUG |
319210
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FDA ORPHAN DRUG |
319910
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FDA ORPHAN DRUG |
320810
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MENATETRENONE
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C52194
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m7171
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DTXSID6048969
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C030814
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Related Record | Type | Details | ||
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ACTIVE MOIETY |