Phytonadione

Summary

Phytonadione (CHEMBL1550) is an approved small-molecule cofactor (ATC B02BA01); indicated across 15 conditions including ulcerative colitis and celiac disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B02BA01
• Indications: 15 conditions
• Clinical trials: 19
• Chemistry: 450.7 Da · C31H46O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1550
Name	Phytonadione
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5284607
ChEBI	CHEBI:18067
ATC	B02BA01
Molecular formula	C31H46O2
Molecular weight	450.7
InChIKey	MBWXNTAXLNYFJB-NKFFZRIASA-N

SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C

IUPAC name: 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione

ChEBI definition: A member of the class of phylloquinones that consists of 1,4-naphthoquinone having methyl and phytyl groups at positions 2 and 3 respectively. The parent of the class of phylloquinones.

Pharmacological roles (ChEBI): cofactor.

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

Also known as: Aquamephyton, Fitomenadiona, Kanavit, Konakion, Konakion mm, Konakion mm paed, Mephyton, Neokay, NSC-270681, Orakay, Phylloquinone e-form, Phytomenadione

Patent coverage: 32,941 distinct patent families (83,772 SureChEMBL compound mentions), from 1 matched compound structure(s). 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: 4 (assay-derived). Sample: Prostaglandin G/H synthase 1, cGMP-inhibited 3’,5’-cyclic phosphodiesterase 3A, 3’,5’-cyclic-AMP phosphodiesterase 4A, Alpha-synuclein.

Bioactivity

ChEMBL activities: 2 potent at pChembl ≥ 5 of 4 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PDE3A	5.46	AC50	3437	nM	CHEMBL_ACT_25192032
PDE4A	5.02	AC50	9524	nM	CHEMBL_ACT_25207402

Target pathways

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

Indications & clinical

Indications

15 indications (6 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
ulcerative colitis	4	MONDO:0005101	EFO:0000729
celiac disease	4	MONDO:0005130	EFO:0001060
vitamin K deficiency hemorrhagic disease	4	MONDO:0001244	MONDO:0024298
cystic fibrosis	4	MONDO:0009061	MONDO:0009061
cardiovascular disorder	3	MONDO:0004995	EFO:0000319
osteoporosis	3	MONDO:0005298	EFO:0003882
postmenopausal osteoporosis	2	MONDO:0008159	EFO:0003854
chronic kidney disease	2	MONDO:0005300	EFO:0003884
glioblastoma	2	MONDO:0018177	EFO:0000519
rheumatoid arthritis	1	MONDO:0008383	EFO:0000685
chronic hepatitis B virus infection	1	MONDO:0005366	EFO:0004239
intracerebral hemorrhage	0	MONDO:0013792	EFO:0005669

3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 19.

Phase distribution

Phase	Trials
Not specified	6
PHASE3	3
PHASE2	3
PHASE1	3
PHASE2/PHASE3	2
PHASE4	1
EARLY_PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06839352	PHASE4	COMPLETED	Efficacy and Safety of Intravenous Vitamin K1 in Management of Acute Variceal Bleeding
NCT05018221	PHASE3	RECRUITING	Better Evidence and Translation for Calciphylaxis
NCT00062595	PHASE3	COMPLETED	Vitamin K and Bone Turnover in Postmenopausal Women
NCT01232647	PHASE2/PHASE3	UNKNOWN	Vitamin K as Additive Treatment in Osteoporosis
NCT01742273	PHASE3	TERMINATED	Vitamin K1 to Slow Progression of Vascular Calcification in HD Patients
NCT04477811	PHASE2/PHASE3	COMPLETED	Comparative Study Evaluating the Effect of Vitamin K1 Versus Vitamin K2 on Vascular Calcification in Dialysis Patients
NCT04752813	PHASE2	ACTIVE_NOT_RECRUITING	A Study of BPM31510 With Vitamin K1 in Subjects With Newly Diagnosed Glioblastoma (GB)
NCT01528800	PHASE2	COMPLETED	Vitamin K to Attenuate Coronary Artery Calcification in Hemodialysis Patients
NCT02324686	PHASE2	COMPLETED	Vitamin K Supplementation in Patients on Hemodialysis
NCT02256813	PHASE1	COMPLETED	Study to Evaluate the Effect of Multiple Doses of BIRT 2584 XX Tablets on the Pharmacokinetic Parameters of Warfarin, Omeprazole, Caffeine, and Dextromethorphan in Healthy Male Volunteers
NCT05273775	PHASE1	COMPLETED	A Pharmacokinetic Study to Evaluate the Drug Interaction Between HRS5091 and Probe Drugs in Healthy Volunteers
NCT05392127	PHASE1	COMPLETED	A Pharmacokinetic Study to Evaluate the Drug Interaction Between SHR0302 and CYP Substrates in Healthy Volunteers
NCT03388970	EARLY_PHASE1	UNKNOWN	Vitamin K1 in the Treatment of Spontaneous Intracerebral Hemorrhage
NCT00905229	Not specified	WITHDRAWN	Comparing Different Routes and Doses of Phytonadione (Vitamin K) for Reversing Warfarin Treated Patients With Hip Fracture Before Surgery
NCT01194778	Not specified	COMPLETED	Comparison of Efficacy of Different Dosages Vitamin K2
NCT01474460	Not specified	COMPLETED	Use of Phytonadione to Reduce International Normalized Ratio (INR) Variability in Patients on Long-term Warfarin Therapy
NCT03782025	Not specified	COMPLETED	Effect of Vitamin K in Critically Ill Patients
NCT04247087	Not specified	COMPLETED	Effects of Fhytomenadione on Coronary Artery Calcification of Hemodialysis Patients
NCT05713045	Not specified	COMPLETED	Late Vitamin K Deficiency-related Bleeding in Neonates (VKLB): Comparison of Different Strategies to Prophylaxis

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

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