Accession NumberDB01022  (APRD00464, DB09528)
TypeSmall Molecule

Phylloquinone is often called vitamin K1. It is a fat-soluble vitamin that is stable to air and moisture but decomposes in sunlight. It is found naturally in a wide variety of green plants. Phylloquinone is also an antidote for coumatetralyl. Vitamin K is needed for the posttranslational modification of certain proteins, mostly required for blood coagulation.

Vitamin k
Vitamin K1
External IDs NSC-270681
Product Ingredients Not Available
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AquamephytonInjection, emulsion10 mg/mLIntramuscular; Intravenous; SubcutaneousTeligent Pharma, Inc.2017-05-25Not applicableUs
AquamephytonInjection, emulsion2 mg/mLIntramuscular; Intravenous; SubcutaneousTeligent Pharma, Inc.2017-05-25Not applicableUs
MephytonTablet5 mg/1OralKaiser Foundations Hospitals2013-07-29Not applicableUs00187 1704 05 nlmimage10 e045f00f
MephytonTablet5 mg/1OralValeant Pharmaceuticals North America2013-03-19Not applicableUs
MephytonTablet5 mg/1OralA S Medication Solutions2013-03-192017-06-20Us
MephytonTablet5 mg/1OralPhysicians Total Care, Inc.2006-03-21Not applicableUs
MephytonTablet5 mg/1OralRebel Distributors1955-09-30Not applicableUs
MephytonTablet5 mg/1OralCarilion Materials Management2013-03-19Not applicableUs
MephytonTablet5 mg/1OralCardinal Health1955-09-30Not applicableUs
MephytonTablet5 mg/1OralPd Rx Pharmaceuticals, Inc.1955-09-302017-04-14Us
MephytonTablet5 mg/1OralAvera Mc Kennan Hospital2015-03-09Not applicableUs
PhytonadioneTablet5 mg/1OralOceanside Pharmaceuticals2017-02-012017-05-25Us
Phytonadione Inj 2mg/mlLiquid2 mgIntramuscularInternational Medication Systems, Limited1971-12-311997-08-15Canada
Vitamin K1 Inj 10mg/mlSolution10 mgIntramuscular; Intravenous; SubcutaneousHospira, Inc.1981-12-31Not applicableCanada
Vitamin K1 Inj 10mg/ml USPEmulsion10 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1989-12-31Not applicableCanada
Vitamin K1 Inj 1mg/0.5ml USPEmulsion2 mgIntramuscular; Intravenous; SubcutaneousSandoz Canada Incorporated1989-12-31Not applicableCanada
Vitamin K1 Inj 2mg/mlSolution2 mgIntramuscular; Intravenous; SubcutaneousHospira, Inc.1981-12-31Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PhytonadioneInjection, emulsion1 mg/.5mLParenteralInternational Medication Systems, Limited2003-04-18Not applicableUs
PhytonadioneInjection, emulsion1 mg/.5mLParenteralAmphastar Pharmaceuticals, Inc.1988-03-242016-12-06Us
PhytonadioneInjection, solution1 mg/.5mLIntramuscular; Parenteral; SubcutaneousGeneral Injectables & Vaccines2010-04-012017-01-25Us
PhytonadioneInjection, emulsion1 mg/.5mLParenteralAmphastar Pharmaceuticals, Inc.2003-04-182016-12-06Us
PhytonadioneInjection, emulsion1 mg/.5mLParenteralGeneral Injectables & Vaccines2013-02-13Not applicableUs
PhytonadioneInjection, emulsion1 mg/.5mLParenteralCardinal Health2003-04-18Not applicableUs
PhytonadioneInjection, emulsion1 mg/.5mLParenteralGeneral Injectables & Vaccines2014-01-06Not applicableUs
PhytonadioneInjection, emulsion1 mg/.5mLParenteralGeneral Injectables & Vaccines2012-09-14Not applicableUs
Vitamin K1Injection, emulsion10 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1983-07-25Not applicableUs
Vitamin K1Injection, emulsion2 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1983-07-25Not applicableUs
Vitamin K1Injection, emulsion2 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2011-08-24Not applicableUs
Vitamin K1Injection, solution10 mg/mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2010-09-01Not applicableUs
Vitamin K1Injection, emulsion10 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2011-08-24Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
Aqua-MephytonNot Available
KonakionNot Available
Brand mixtures
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Adult Infuvite Multiple VitaminsInjection, solutionIntravenousSandoz2005-05-18Not applicableUs
Infuvite Adult Multiple VitaminsInjection, solutionIntravenousSandoz2005-05-18Not applicableUs
M.V.I. PaediatricLiquidIntravenousAventis Pharma Ltd.1988-12-312002-07-29Canada
M.V.I. PediatricInjection, powder, lyophilized, for solutionIntravenousHospira Worldwide, Inc.1983-04-06Not applicableUs
Multi-12/k1 PediatricLiquidIntravenousSandoz Canada Incorporated2000-11-07Not applicableCanada
Pediatric Infuvite Multiple VitaminsInjection, solutionIntravenousSandoz2001-02-21Not applicableUs
Pediatric Infuvite Multiple Vitamins for InfusionInjection, solutionIntravenousSandoz2001-02-21Not applicableUs
CAS number84-80-0
WeightAverage: 450.6957
Monoisotopic: 450.349780716
Chemical FormulaC31H46O2

For the treatment of haemorrhagic conditions in infants, antidote for coumarin anticoagulants in hypoprothrombinaemia.

Structured Indications

Phylloquinone is a vitamin, indicated in the treatment of coagulation disorders which are due to faulty formation of factors II, VII, IX and X when caused by vitamin K deficiency or interference with vitamin K activity. Phylloquinone aqueous colloidal solution of vitamin K1 for parenteral injection, possesses the same type and degree of activity as does naturally-occurring vitamin K, which is necessary for the production via the liver of active prothrombin (factor II), proconvertin (factor VII), plasma thromboplastin component (factor IX), and Stuart factor (factor X).

Mechanism of action

Vitamin K is an essential cofactor for the gamma-carboxylase enzymes which catalyze the posttranslational gamma-carboxylation of glutamic acid residues in inactive hepatic precursors of coagulation factors II (prothrombin), VII, IX and X. Gamma-carboxylation converts these inactive precursors into active coagulation factors which are secreted by hepatocytes into the blood. Supplementing with Phylloquinone results in a relief of vitamin K deficiency symptoms which include easy bruisability, epistaxis, gastrointestinal bleeding, menorrhagia and hematuria.

TargetKindPharmacological actionActionsOrganismUniProt ID
Vitamin K-dependent gamma-carboxylaseProteinyes
HumanP38435 details
HumanP02818 details
Related Articles

Oral phylloquinone is adequately absorbed from the gastrointestinal tract only if bile salts are present. After absorption, phylloquinone is initially concentrated in the liver, but the concentration declines rapidly. Very little vitamin K accumulates in tissues.

Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of elimination

Almost no free unmetabolized vitamin K appears in bile or urine.

Half lifeNot Available
ClearanceNot Available

The intravenous LD50 of phylloquinone in the mouse is 41.5 and 52 mL/kg for the 0.2% and 1% concentrations, respectively.

Affected organisms
  • Humans and other mammals
PathwayCategorySMPDB ID
Tranexamic Acid Action PathwayDrug actionSMP00287
Vitamin K MetabolismMetabolicSMP00464
Dicumarol Action PathwayDrug actionSMP00270
Ardeparin Action PathwayDrug actionSMP00275
Streptokinase Action PathwayDrug actionSMP00282
Argatroban Action PathwayDrug actionSMP00276
Lepirudin Action PathwayDrug actionSMP00278
Alteplase Action PathwayDrug actionSMP00280
Anistreplase Action PathwayDrug actionSMP00281
Tenecteplase Action PathwayDrug actionSMP00283
Phenindione Action PathwayDrug actionSMP00655
Urokinase Action PathwayDrug actionSMP00284
Aprotinin Action PathwayDrug actionSMP00288
Coagulation PhysiologicalSMP00586
Dicoumarol Action PathwayDrug actionSMP00656
Warfarin Action PathwayDrug actionSMP00268
Acenocoumarol Action PathwayDrug actionSMP00269
Phenprocoumon Action PathwayDrug actionSMP00271
Enoxaparin Action PathwayDrug actionSMP00272
Fondaparinux Action PathwayDrug actionSMP00273
Heparin Action PathwayDrug actionSMP00274
Bivalirudin Action PathwayDrug actionSMP00277
Ximelagatran Action PathwayDrug actionSMP00279
Reteplase Action PathwayDrug actionSMP00285
Aminocaproic Acid Action PathwayDrug actionSMP00286
Pharmacogenomic Effects/ADRs Not Available
Drug Interactions
DrugInteractionDrug group
AcenocoumarolPhylloquinone may decrease the anticoagulant activities of Acenocoumarol.Approved
DicoumarolPhylloquinone may decrease the anticoagulant activities of Dicoumarol.Approved
Ethyl biscoumacetatePhylloquinone may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
Fibrinogen HumanThe risk or severity of adverse effects can be increased when Phylloquinone is combined with Fibrinogen Concentrate (Human).Approved
FluindionePhylloquinone may decrease the anticoagulant activities of Fluindione.Investigational
OrlistatThe serum concentration of Phylloquinone can be decreased when it is combined with Orlistat.Approved, Investigational
PhenindionePhylloquinone may decrease the anticoagulant activities of Phenindione.Approved
PhenprocoumonPhylloquinone may decrease the anticoagulant activities of Phenprocoumon.Approved
TretinoinTretinoin may increase the thrombogenic activities of Phylloquinone.Approved, Investigational, Nutraceutical
WarfarinPhylloquinone may decrease the anticoagulant activities of Warfarin.Approved
Food InteractionsNot Available
Synthesis Reference

Manfred Dorner, "Method of making vitamin K1." U.S. Patent US5744624, issued June, 1964.

General ReferencesNot Available
External Links
ATC CodesB02BA01 — Phytomenadione
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (72 KB)
Clinical Trials
Clinical Trials
1Active Not RecruitingOtherNeoplasms1
1CompletedNot AvailableThrombosis, Venous1
1CompletedBasic ScienceRheumatoid Arthritis1
1CompletedTreatmentHealthy Volunteers4
2RecruitingPreventionEndstage Kidney Disease1
2RecruitingTreatmentEnd Stage Renal Failure on Dialysis / Nonvalvular Atrial Fibrillation1
2, 3RecruitingTreatmentOsteoporosis, Post-Menopausal1
3CompletedTreatmentBone destruction / Calcifications, Vascular / Inflammatory Reaction1
3CompletedTreatmentCoagulation / Haemorrhage / Thrombosis2
3CompletedTreatmentBone destruction1
3RecruitingTreatmentCardiovascular Disease (CVD)1
Not AvailableCompletedBasic ScienceAging / Bone destruction1
Not AvailableCompletedBasic SciencePharmacokinetics1
Not AvailableCompletedTreatmentAnticoagulants / Warfarin1
Not AvailableCompletedTreatmentEcchymosis1
Not AvailableUnknown StatusPreventionBMI >27 kg/m2 / Bone Density1
Not AvailableWithdrawnTreatmentComplications / Haemorrhage1
  • Eli lilly and co
  • Hoffmann la roche inc
  • Aton pharma inc
  • Glaxosmithkline
  • International medication system
  • Hospira inc
Dosage forms
Injection, powder, lyophilized, for solutionIntravenous
TabletOral5 mg/1
Injection, solutionIntravenous
Injection, emulsionParenteral1 mg/.5mL
Injection, solutionIntramuscular; Parenteral; Subcutaneous1 mg/.5mL
LiquidIntramuscular2 mg
Injection, emulsionIntramuscular; Intravenous; Subcutaneous10 mg/mL
Injection, emulsionIntramuscular; Intravenous; Subcutaneous2 mg/mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous10 mg/mL
SolutionIntramuscular; Intravenous; Subcutaneous10 mg
EmulsionIntramuscular; Intravenous; Subcutaneous10 mg
EmulsionIntramuscular; Intravenous; Subcutaneous2 mg
SolutionIntramuscular; Intravenous; Subcutaneous2 mg
Unit descriptionCostUnit
Phytonadione crystal111.13USD g
Phytonadione liquid66.0USD g
Vitamin k1 liquid35.0USD g
Mephyton 5 mg tablet5.95USD tablet
Vitamin K1 Pediatric 2 mg/ml4.79USD ml
Vitamin K1 10 mg/ml2.76USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Experimental Properties
melting point (°C)-20 °CPhysProp
boiling point (°C)142.5 °C at 1.00E-03 mm HgPhysProp
water solubilityInsoluble in waterNot Available
logP9.3Not Available
Predicted Properties
Water Solubility5.92e-05 mg/mLALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity142.96 m3·mol-1ChemAxon
Polarizability55.92 Å3ChemAxon
Number of Rings2ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8941
Caco-2 permeable+0.7993
P-glycoprotein substrateSubstrate0.6643
P-glycoprotein inhibitor IInhibitor0.8581
P-glycoprotein inhibitor IIInhibitor0.9503
Renal organic cation transporterNon-inhibitor0.7232
CYP450 2C9 substrateNon-substrate0.7852
CYP450 2D6 substrateNon-substrate0.827
CYP450 3A4 substrateSubstrate0.6854
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7542
Ames testNon AMES toxic0.8945
BiodegradationNot ready biodegradable0.9051
Rat acute toxicity1.1603 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5675
hERG inhibition (predictor II)Inhibitor0.5
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Mass Spec (NIST)Not Available
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0002-1290000000-fa752c2db990f115c3c6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-8269080000-4bdc9b3a41d7d08b7265View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0002-7379080000-ba90762b738ee84b3151View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-6749020000-c4e58ef0e538e224dad4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0g4i-3149020000-ad93d4a26002eefa74ceView in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00xr-5397040000-221a2f93d46494325e33View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udl-9740400000-e47d11ed7b15a667d611View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0udi-2540900000-d08585615fbc2418786aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
DescriptionThis compound belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentVitamin K compounds
Alternative ParentsDiterpenoids / Naphthoquinones / Quinones / Aryl ketones / Organic oxides / Hydrocarbon derivatives
SubstituentsDiterpenoid / Naphthoquinone / Naphthalene / Aryl ketone / Quinone / Benzenoid / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptorsphylloquinones (CHEBI:18067 ) / Vitamin K (LMPR02030028 )


Pharmacological action
General Function:
Gamma-glutamyl carboxylase activity
Specific Function:
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vitamin K to vitamin K epoxide.
Gene Name:
Uniprot ID:
Uniprot Name:
Vitamin K-dependent gamma-carboxylase
Molecular Weight:
87560.065 Da
  1. Morris DP, Soute BA, Vermeer C, Stafford DW: Characterization of the purified vitamin K-dependent gamma-glutamyl carboxylase. J Biol Chem. 1993 Apr 25;268(12):8735-42. [PubMed:8473318 ]
  2. Tuan RS: Vitamin K-dependent gamma-glutamyl carboxylase activity in the chick embryonic chorioallantoic membrane. J Biol Chem. 1979 Feb 25;254(4):1356-64. [PubMed:105006 ]
  3. Reedstrom CK, Suttie JW: Comparative distribution, metabolism, and utilization of phylloquinone and menaquinone-9 in rat liver. Proc Soc Exp Biol Med. 1995 Sep;209(4):403-9. [PubMed:7638250 ]
  4. Tasatargil A, Cadir B, Dalaklioglu S, Yurdakonar E, Caglar S, Turkay C: Effects of vitamin K1 supplementation on vascular responsiveness and oxidative stress in a rat femoral osteotomy model. Cell Biochem Funct. 2007 Sep-Oct;25(5):485-90. [PubMed:16929463 ]
  5. Olson RE: The function and metabolism of vitamin K. Annu Rev Nutr. 1984;4:281-337. [PubMed:6380538 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Pharmacological action
General Function:
Structural molecule activity
Specific Function:
Constitutes 1-2% of the total bone protein. It binds strongly to apatite and calcium.
Gene Name:
Uniprot ID:
Uniprot Name:
Molecular Weight:
10962.445 Da
  1. Sato Y, Tsuru T, Oizumi K, Kaji M: Vitamin K deficiency and osteopenia in disuse-affected limbs of vitamin D-deficient elderly stroke patients. Am J Phys Med Rehabil. 1999 Jul-Aug;78(4):317-22. [PubMed:10418836 ]
  2. Schurgers LJ, Dissel PE, Spronk HM, Soute BA, Dhore CR, Cleutjens JP, Vermeer C: Role of vitamin K and vitamin K-dependent proteins in vascular calcification. Z Kardiol. 2001;90 Suppl 3:57-63. [PubMed:11374034 ]
  3. Vermeer C, Wolf J, Craciun AM, Knapen MH: Bone markers during a 6-month space flight: effects of vitamin K supplementation. J Gravit Physiol. 1998 Oct;5(2):65-9. [PubMed:11541904 ]
  4. Askim M: [Vitamin K in the Norwegian diet and osteoporosis]. Tidsskr Nor Laegeforen. 2001 Sep 20;121(22):2614-6. [PubMed:11668761 ]
  5. Kawana K, Takahashi M, Hoshino H, Kushida K: Circulating levels of vitamin K1, menaquinone-4, and menaquinone-7 in healthy elderly Japanese women and patients with vertebral fractures and patients with hip fractures. Endocr Res. 2001 Aug;27(3):337-43. [PubMed:11678581 ]
Drug created on June 13, 2005 07:24 / Updated on August 02, 2017 16:29