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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
Structure of MENATETRENONE

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+

HIDE SMILES / InChI

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

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Glakay

Approved Use

Improvement of decrease in bone mass and relief of pain in patients with osteoporosis

Launch Date

1.10445121E12
PubMed

PubMed

TitleDatePubMed
Prevention of hepatocarcinogenesis with phosphatidylcholine and menaquinone-4: in vitro and in vivo experiments.
2007 Jul
Identification of UBIAD1 as a novel human menaquinone-4 biosynthetic enzyme.
2010 Nov 4
Synthesis of novel vitamin K2 analogues with modification at the ω-terminal position and their biological evaluation as potent steroid and xenobiotic receptor (SXR) agonists.
2011 Jun 23
Patents

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
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
by admin
on Fri Dec 15 16:23:28 UTC 2023
Edited
by admin
on Fri Dec 15 16:23:28 UTC 2023
Record UNII
27Y876D139
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MENATETRENONE
INN   MART.   WHO-DD  
INN  
Official Name English
VITAMIN K2(20)
Common Name English
MENAQUINONE 4 [MI]
Common Name English
MENATETRENONE [JAN]
Common Name English
MENATETRANONE
Common Name English
MENATETRENONE [MART.]
Common Name English
KAYTWO
Brand Name English
MENAQUINONE-4 [USP-RS]
Common Name English
menatetrenone [INN]
Common Name English
MENAQUINONE-4
Common Name English
Menatetrenone [WHO-DD]
Common Name English
KAYTWO N
Brand Name English
2-METHYL-3-(3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL)-1,4-NAPHTHOQUINONE
Systematic Name English
1,4-NAPHTHALENEDIONE, 2-METHYL-3-((2E,6E,10E)3,7,11,15-TETRAMETHYL-2,6,10,14-HEXADECATETRAENYL)-
Systematic Name English
MENAQUINONE 4
MI  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C26017
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
FDA ORPHAN DRUG 319110
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
FDA ORPHAN DRUG 348111
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
FDA ORPHAN DRUG 319210
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
FDA ORPHAN DRUG 319910
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
FDA ORPHAN DRUG 320810
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
Code System Code Type Description
INN
3292
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
FDA UNII
27Y876D139
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
DRUG CENTRAL
1685
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL259223
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PUBCHEM
5282367
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PRIMARY
CAS
863-61-6
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PRIMARY
MESH
D024482
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
DRUG BANK
DB12148
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
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RS_ITEM_NUM
1381083
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
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CHEBI
78277
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
WIKIPEDIA
MENATETRENONE
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
NCI_THESAURUS
C52194
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
MERCK INDEX
m7171
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY Merck Index
CHEBI
16374
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
SMS_ID
100000081471
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
RXCUI
29495
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY RxNorm
EVMPD
SUB08736MIG
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID6048969
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
MESH
C030814
Created by admin on Fri Dec 15 16:23:28 UTC 2023 , Edited by admin on Fri Dec 15 16:23:28 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY