Menatetrenone

Summary

Menatetrenone (CHEMBL259223) is a phase-3 clinical-stage small-molecule bone density conservation agent (ATC M05BX08); indicated across 4 conditions including postmenopausal osteoporosis and osteoporosis.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• ATC class: M05BX08
• Indications: 4 conditions
• Clinical trials: 21
• Chemistry: 444.6 Da · C31H40O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL259223
Name	Menatetrenone
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	5282367
ChEBI	CHEBI:78277
ATC	M05BX08
Molecular formula	C31H40O2
Molecular weight	444.6
InChIKey	DKHGMERMDICWDU-GHDNBGIDSA-N

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

IUPAC name: 2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl]naphthalene-1,4-dione

ChEBI definition: A menaquinone whose side-chain contains 4 isoprene units in an all-trans-configuration.

Pharmacological roles (ChEBI): bone density conservation agent, antioxidant, anti-inflammatory agent, neuroprotective agent.

Other ChEBI roles (chemical / environmental): human metabolite.

Also known as: Kaytwo, Kaytwo n, Menaquinone 4, Menaquinone-4, Menatetranone, Menatetrenona, Menatetrenone, Vitamin k2(20), menatetrenone, SID11533054, Vitamin K2, SID144204118

Parent form; salt/anhydrous children: CHEMBL2024142, CHEMBL2024143

Patent coverage: 876 distinct patent families (2,178 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 1,537 (71%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 13 (assay-derived). Sample: Microtubule-associated protein tau, Fructose-bisphosphate aldolase, 4’-phosphopantetheinyl transferase ffp, Progesterone receptor, 5-hydroxytryptamine receptor 1A, Prostaglandin G/H synthase 1, D(3) dopamine receptor, cGMP-inhibited 3’,5’-cyclic phosphodiesterase 3A, 3’,5’-cyclic-AMP phosphodiesterase 4A, Adenosine receptor A3.

Bioactivity

ChEMBL activities: 6 potent at pChembl ≥ 5 of 15 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGS1	6.11	AC50	780.1	nM	CHEMBL_ACT_25206485
DRD3	5.54	AC50	2906	nM	CHEMBL_ACT_25194844
ADORA3	5.33	AC50	4716	nM	CHEMBL_ACT_25198980
MAPK1	5.3	Potency	5012	nM	CHEMBL_ACT_4729662
PDE3A	5.29	AC50	5086	nM	CHEMBL_ACT_25192048
PDE4A	5.07	AC50	8528	nM	CHEMBL_ACT_25207418

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

4 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
postmenopausal osteoporosis	3	MONDO:0008159	EFO:0003854
osteoporosis	3	MONDO:0005298	EFO:0003882
bone disorder	3	MONDO:0005381	EFO:0004260
hepatocellular carcinoma	2	MONDO:0007256	EFO:0000182

Clinical trials

Total trials: 21.

Phase distribution

Phase	Trials
Not specified	9
PHASE4	4
PHASE2/PHASE3	4
PHASE3	2
PHASE2	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00165607	PHASE4	COMPLETED	Randomized, Open, Parallel, Active Controlled Study on Fracture Prevention in Antiosteoporosis Treatment (OF Study)
NCT00960973	PHASE4	COMPLETED	The Effect of Vitamin K Supplementation on Glucose Metabolism
NCT01101698	PHASE4	UNKNOWN	Vitamin K2 and Vessel Calcification in Chronic Kidney Disease Patients
NCT02610933	PHASE4	COMPLETED	Effect on Vascular Calcification of Replacing Warfarin by Rivaroxaban With or Without VitK2 in Hemodialysis Patients
NCT00062595	PHASE3	COMPLETED	Vitamin K and Bone Turnover in Postmenopausal Women
NCT00165633	PHASE2/PHASE3	TERMINATED	A Phase II/III Clinical Study on Inhibitory Effects of E0167 on Recurrence of Hepatocellular Carcinoma
NCT00165698	PHASE3	COMPLETED	Efficacy and Safety Study on Menatetrenone in the Treatment of Postmenopausal Osteoporosis Women
NCT01232647	PHASE2/PHASE3	UNKNOWN	Vitamin K as Additive Treatment in Osteoporosis
NCT04145492	PHASE2/PHASE3	UNKNOWN	Effect of Vitamin K 2 on Vascular Calcification in Hemodialysis Patients
NCT04477811	PHASE2/PHASE3	COMPLETED	Comparative Study Evaluating the Effect of Vitamin K1 Versus Vitamin K2 on Vascular Calcification in Dialysis Patients
NCT01533441	PHASE2	COMPLETED	Vitamin K2 Intervention in Patients With Vitamin K Antagonists
NCT02917525	PHASE2	UNKNOWN	Bicuspid Aortic Valve Stenosis and the Effect of vItamin K2 on Calciummetabolism on 18F-NaF PET/MRI
NCT06817512	Not specified	ACTIVE_NOT_RECRUITING	Ischemic Stroke Nutrition Intervention Study
NCT01194778	Not specified	COMPLETED	Comparison of Efficacy of Different Dosages Vitamin K2
NCT04429035	Not specified	UNKNOWN	SLOW-Slower Progress of caLcificatiOn With Vitamin K2
NCT04676958	Not specified	COMPLETED	viTAmin K2 and rEcOVery From ExeRcise
NCT05161975	Not specified	UNKNOWN	Vitamin K2 Supplements for Muscle Recovery
NCT05375630	Not specified	UNKNOWN	Vitamin K2 and Muscle Weakness in Type 2 Diabetes
NCT05547750	Not specified	COMPLETED	Effect of Vitamin K2 in the Treatment of Nocturnal Leg Cramps in Older Population
NCT05675163	Not specified	COMPLETED	Antioxidant and Immune Effects of Vitamin K2
NCT05995522	Not specified	COMPLETED	Effect of Vitamin K2 Over Osteocalcin, Leptin, Cytokines, and Cardiovascular Risk in Young Adults With Overweight and Obesity

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).