Identification

Name
Phylloquinone
Accession Number
DB01022  (APRD00464, DB09528)
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione
  • 2-Methyl-3-[(2e)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone
  • 2-Methyl-3-phytyl-1,4-naphthochinon
  • 2-Methyl-3-phytyl-1,4-naphthoquinone
  • 3-Phytylmenadione
  • alpha-Phylloquinone
  • Fitomenadiona
  • Phyllochinon
  • Phyllochinonum
  • Phylloquinone
  • Phythyl-menadion
  • Phytomenadione
  • Phytomenadionum
  • Phytonadionum
  • Phytylmenadione
  • trans-Phylloquinone
  • Vitamin k
  • Vitamin K1
  • α-phylloquinone
External IDs
NSC-270681
Product Images
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/1OralA S Medication Solutions2013-03-192017-06-20Us
MephytonTablet5 mg/1OralValeant Pharmaceuticals North America2013-03-19Not applicableUs
MephytonTablet5 mg/1OralPd Rx Pharmaceuticals, Inc.1955-09-302017-04-14Us
MephytonTablet5 mg/1OralCarilion Materials Management2013-03-19Not applicableUs
MephytonTablet5 mg/1OralRebel Distributors1955-09-30Not applicableUs
MephytonTablet5 mg/1OralPhysicians Total Care, Inc.2006-03-21Not applicableUs
MephytonTablet5 mg/1OralAvera Mc Kennan Hospital2015-03-09Not applicableUs
MephytonTablet5 mg/1OralKaiser Foundations Hospitals2013-07-29Not applicableUs00187 1704 05 nlmimage10 e045f00f
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PhytonadioneInjection, emulsion1 mg/.5mLParenteralAmphastar Pharmaceuticals, Inc.1988-03-242016-12-06Us
PhytonadioneInjection, emulsion1 mg/.5mLParenteralGeneral Injectables & Vaccines2014-01-06Not applicableUs
PhytonadioneInjection, emulsion1 mg/.5mLParenteralGeneral Injectables & Vaccines2012-09-14Not applicableUs
PhytonadioneInjection, emulsion1 mg/.5mLParenteralAmphastar Pharmaceuticals, Inc.2003-04-182016-12-06Us
PhytonadioneInjection, emulsion1 mg/.5mLParenteralCardinal Health2003-04-18Not applicableUs
PhytonadioneInjection, solution1 mg/.5mLIntramuscular; Parenteral; SubcutaneousGeneral Injectables & Vaccines2010-04-012017-01-25Us
PhytonadioneInjection, emulsion1 mg/.5mLParenteralGeneral Injectables & Vaccines2013-02-13Not applicableUs
PhytonadioneInjection, emulsion1 mg/.5mLParenteralInternational Medication Systems, Limited2003-04-18Not applicableUs
Vitamin K1Injection, emulsion2 mg/mLIntramuscular; Intravenous; SubcutaneousCardinal Health2011-08-24Not applicableUs
Vitamin K1Injection, emulsion10 mg/mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.1983-07-25Not applicableUs
International/Other Brands
Aqua-Mephyton / Konakion / Phytonadione
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Adult Infuvite Multiple VitaminsPhylloquinone (150 ug/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
Adult Infuvite Multiple VitaminsPhylloquinone (150 ug/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsPhylloquinone (150 ug/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Adult Infuvite Multiple VitaminsPhylloquinone (150 ug/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
Infuvite Adult Multiple VitaminsPhylloquinone (150 ug/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2005-05-18Not applicableUs
Infuvite Adult Multiple VitaminsPhylloquinone (150 ug/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Folic Acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Riboflavin 5'-phosphate sodium (3.6 mg/10mL) + Thiamine Hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + Vitamin C (200 mg/10mL) + Vitamin E acetate (10 [iU]/10mL)Injection, solutionIntravenousSandoz2003-06-16Not applicableUs
M.V.I. PaediatricPhylloquinone (.2 mg) + Biotin (20 mcg) + Cyanocobalamin (1 mcg) + Folic Acid (.14 mg) + Nicotinamide (17 mg) + Pantothenic acid (5 mg) + Pyridoxine hydrochloride (1 mg) + Riboflavin 5'-phosphate sodium (1.4 mg) + Thiamine Hydrochloride (1.2 mg) + Vitamin A (2300 unit) + Vitamin C (80 mg) + Vitamin D (400 unit) + Vitamin E (7 unit)LiquidIntravenousAventis Pharma Ltd.1988-12-312002-07-29Canada
M.V.I. PediatricPhylloquinone (200 ug/5mL) + Biotin (20 ug/5mL) + Cyanocobalamin (1 ug/5mL) + Dexpanthenol (5 mg/5mL) + Ergocalciferol (10 ug/5mL) + Folic Acid (140 ug/5mL) + Nicotinamide (17 mg/5mL) + Pyridoxine hydrochloride (1 mg/5mL) + Riboflavin 5'-phosphate sodium (1.4 mg/5mL) + Thiamine Hydrochloride (1.2 mg/5mL) + Vitamin A (.7 mg/5mL) + Vitamin C (80 mg/5mL) + Vitamin E (7 mg/5mL)Injection, powder, lyophilized, for solutionIntravenousHospira, Inc.1983-04-06Not applicableUs
Multi-12/k1 PediatricPhylloquinone (0.2 mg) + Biotin (20 mcg) + Cyanocobalamin (1 mcg) + Dexpanthenol (5 mg) + Folic Acid (140 mcg) + Nicotinamide (17 mg) + Pyridoxine hydrochloride (1 mg) + Riboflavin (1.4 mg) + Thiamine Hydrochloride (1.2 mg) + Vitamin A (2300 unit) + Vitamin C (80 mg) + Vitamin D (400 unit) + Vitamin E (7 unit)LiquidIntravenousSandoz Canada Incorporated2000-11-07Not applicableCanada
Pediatric Infuvite Multiple VitaminsPhylloquinone (.2 mg/5mL) + Biotin (20 ug/5mL) + Cholecalciferol (400 [iU]/5mL) + Cyanocobalamin (1 ug/5mL) + Dexpanthenol (5 mg/5mL) + Folic Acid (140 ug/5mL) + Nicotinamide (17 mg/5mL) + Pyridoxine hydrochloride (1 mg/5mL) + Riboflavin 5'-phosphate sodium (1.4 mg/5mL) + Thiamine Hydrochloride (1.2 mg/5mL) + Vitamin A palmitate (2300 [iU]/5mL) + Vitamin C (80 mg/5mL) + Vitamin E acetate (7 [iU]/5mL)Injection, solutionIntravenousSandoz2016-12-23Not applicableUs
Categories
UNII
S5Z3U87QHF
CAS number
84-80-0
Weight
Average: 450.6957
Monoisotopic: 450.349780716
Chemical Formula
C31H46O2
InChI Key
MBWXNTAXLNYFJB-NKFFZRIASA-N
InChI
InChI=1S/C31H46O2/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/h7-8,18-20,22-24H,9-17,21H2,1-6H3/b25-20+/t23-,24-/m1/s1
IUPAC Name
2-methyl-3-[(2E,7R,11R)-3,7,11,15-tetramethylhexadec-2-en-1-yl]-1,4-dihydronaphthalene-1,4-dione
SMILES
CC(C)CCC[[email protected]@H](C)CCC[[email protected]@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O

Pharmacology

Indication

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

Structured Indications
Pharmacodynamics

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.

TargetActionsOrganism
AVitamin K-dependent gamma-carboxylase
inducer
Human
UOsteocalcin
agonist
Human
Absorption

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 distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination

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

Half life
Not Available
Clearance
Not Available
Toxicity

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
Pathways
PathwayCategory
Tranexamic Acid Action PathwayDrug action
Vitamin K MetabolismMetabolic
Dicumarol Action PathwayDrug action
Ardeparin Action PathwayDrug action
Streptokinase Action PathwayDrug action
Urokinase Action PathwayDrug action
Aprotinin Action PathwayDrug action
Coagulation Physiological
Dicoumarol Action PathwayDrug action
Argatroban Action PathwayDrug action
Lepirudin Action PathwayDrug action
Alteplase Action PathwayDrug action
Anistreplase Action PathwayDrug action
Tenecteplase Action PathwayDrug action
Phenindione Action PathwayDrug action
Warfarin Action PathwayDrug action
Acenocoumarol Action PathwayDrug action
Phenprocoumon Action PathwayDrug action
Enoxaparin Action PathwayDrug action
Fondaparinux Action PathwayDrug action
Heparin Action PathwayDrug action
Bivalirudin Action PathwayDrug action
Ximelagatran Action PathwayDrug action
Reteplase Action PathwayDrug action
Aminocaproic Acid Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolPhylloquinone may decrease the anticoagulant activities of Acenocoumarol.Approved
ClorindionePhylloquinone may decrease the anticoagulant activities of Clorindione.Experimental
DicoumarolPhylloquinone may decrease the anticoagulant activities of Dicoumarol.Approved
DiphenadionePhylloquinone may decrease the anticoagulant activities of Diphenadione.Experimental
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 Human.Approved
FluindionePhylloquinone may decrease the anticoagulant activities of Fluindione.Investigational
Mineral oilThe serum concentration of Phylloquinone can be decreased when it is combined with Mineral oil.Approved, Vet Approved
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, Investigational
PhenprocoumonPhylloquinone may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
TioclomarolPhylloquinone may decrease the anticoagulant activities of Tioclomarol.Experimental
TretinoinTretinoin may increase the thrombogenic activities of Phylloquinone.Approved, Investigational, Nutraceutical
WarfarinPhylloquinone may decrease the anticoagulant activities of Warfarin.Approved
Food Interactions
Not Available

References

Synthesis Reference

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

US5744624
General References
Not Available
External Links
Human Metabolome Database
HMDB15157
KEGG Drug
D00148
KEGG Compound
C02059
PubChem Compound
5284607
PubChem Substance
46504528
ChemSpider
4447652
ChEBI
18067
ChEMBL
CHEMBL1550
Therapeutic Targets Database
DNC001500
PharmGKB
PA450961
HET
PQN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Phytonadione
ATC Codes
B02BA01 — Phytomenadione
AHFS Codes
  • 88:24.00 — Vitamin K Activity
PDB Entries
1c51 / 1jb0 / 1qzv / 2o01 / 2pps / 2wsc / 2wse / 2wsf / 3lw5 / 3pcq
show 7 more
MSDS
Download (72 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
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

Pharmacoeconomics

Manufacturers
  • Eli lilly and co
  • Hoffmann la roche inc
  • Aton pharma inc
  • Glaxosmithkline
  • International medication system
  • Hospira inc
Packagers
Dosage forms
FormRouteStrength
LiquidIntravenous
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
Prices
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.
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
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
PropertyValueSource
Water Solubility5.92e-05 mg/mLALOGPS
logP8.48ALOGPS
logP9.7ChemAxon
logS-6.9ALOGPS
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
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
CarcinogenicityNon-carcinogens0.9183
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0002-1290000000-fa752c2db990f115c3c6
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0002-8269080000-4bdc9b3a41d7d08b7265
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0002-7379080000-ba90762b738ee84b3151
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-014i-6749020000-c4e58ef0e538e224dad4
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-0g4i-3149020000-ad93d4a26002eefa74ce
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-00xr-5397040000-221a2f93d46494325e33
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0udl-9740400000-e47d11ed7b15a667d611
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-2540900000-d08585615fbc2418786a
GC-MS Spectrum - GC-MSGC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7
GC-MS Spectrum - GC-MSGC-MSsplash10-0002-1290000000-fa752c2db990f115c3c6
GC-MS Spectrum - GC-MSGC-MSsplash10-0002-8269080000-4bdc9b3a41d7d08b7265
GC-MS Spectrum - GC-MSGC-MSsplash10-0002-7379080000-ba90762b738ee84b3151
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-6749020000-c4e58ef0e538e224dad4
GC-MS Spectrum - GC-MSGC-MSsplash10-0g4i-3149020000-ad93d4a26002eefa74ce
GC-MS Spectrum - GC-MSGC-MSsplash10-00xr-5397040000-221a2f93d46494325e33
GC-MS Spectrum - GC-MSGC-MSsplash10-002r-2930000000-2b32596edebbe7e02cf7
GC-MS Spectrum - GC-MSGC-MSsplash10-0002-1290000000-fa752c2db990f115c3c6
GC-MS Spectrum - GC-MSGC-MSsplash10-0002-8269080000-4bdc9b3a41d7d08b7265
GC-MS Spectrum - GC-MSGC-MSsplash10-0002-7379080000-ba90762b738ee84b3151
GC-MS Spectrum - GC-MSGC-MSsplash10-014i-6749020000-c4e58ef0e538e224dad4
GC-MS Spectrum - GC-MSGC-MSsplash10-0g4i-3149020000-ad93d4a26002eefa74ce
GC-MS Spectrum - GC-MSGC-MSsplash10-00xr-5397040000-221a2f93d46494325e33
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Quinone and hydroquinone lipids
Direct Parent
Vitamin K compounds
Alternative Parents
Diterpenoids / Naphthoquinones / Quinones / Aryl ketones / Organic oxides / Hydrocarbon derivatives
Substituents
Diterpenoid / Naphthoquinone / Naphthalene / Aryl ketone / Quinone / Benzenoid / Ketone / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
phylloquinones (CHEBI:18067) / Vitamin K (LMPR02030028)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inducer
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 vit...
Gene Name
GGCX
Uniprot ID
P38435
Uniprot Name
Vitamin K-dependent gamma-carboxylase
Molecular Weight
87560.065 Da
References
  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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Structural molecule activity
Specific Function
Constitutes 1-2% of the total bone protein. It binds strongly to apatite and calcium.
Gene Name
BGLAP
Uniprot ID
P02818
Uniprot Name
Osteocalcin
Molecular Weight
10962.445 Da
References
  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 November 19, 2017 20:34