Vitamin K1

Identification

Summary

Vitamin K1 is a fat soluble vitamin used to treat hemorrhagic conditions in infants and coumarin overdoses.

Brand Names

Aquamephyton, Infuvite, Infuvite Pediatric, Mephyton, Mvi Pediatric, Phytonadione

Generic Name

Phylloquinone
Commonly known or available as Vitamin K1

DrugBank Accession Number

DB01022

Background

Vitamin K1, also called phylloquinone or phytonadione, is a fat soluble vitamin.^17,18 Phylloquinone is a cofactor of the enzyme γ-carboxylase, which modifies and activates precursors to coagulation factors II, VII, IX, and X.^7,8,6 It is indicated in the treatment of coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by deficiency or interference in the activity of vitamin K.¹⁷

Phylloquinone has been synthesized since at least 1939,¹⁶ and was approved by the FDA prior to 1955.¹⁹

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 450.6957
Monoisotopic: 450.349780716
Chemical Formula: C₃₁H₄₆O₂

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
Phytonadione
Phytonadionum
Phytylmenadione
trans-Phylloquinone
Vitamin K
Vitamin K1
α-phylloquinone

External IDs

NSC-270681

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Pharmacology

Indication

Oral phylloquinone is indicated to treat prothrombin deficiency caused by coumarin or indanedione derivatives; and hypoprothrombinemia secondary to antibacterial therapy, salicylates, or obstructive jaundice or biliary fistulas with concomitant bile salt administration.¹⁸

Parenteral (intravenous, intramuscular, and subcutaneous) phylloquinone is indicated to treat coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by vitamin K deficiency or some interference with vitamin K activity.¹⁷ These indications include the above indications as well as hypoprothrombinemia secondary to sprue, ulcerative colitis, celiac disease, intestinal resection, pancreatic cystic fibrosis, or regional enteritis; or hypoprothrombinemia caused by interference with vitamin k metabolism.¹⁷

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Associated Conditions

Indication Type	Indication	Approval Level	Patient Characteristics	Dose Form
Treatment of	Coagulation disorders	••••••••••••		•••••••••
Treatment of	Hypoprothrombinemia	••• •••••
Treatment of	Hypoprothrombinemia	••••••••••••	••••••••••••• •••••••	•••••••••• ••••••
Treatment of	Hypoprothrombinemia	••••••••••••		•••••••••
Treatment of	Hypoprothrombinemia	••••••••••••		•••••••••

Associated Therapies

Vitamin supplementation

Contraindications & Blackbox Warnings

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Pharmacodynamics

Phylloquinone is a vitamin K indicated in the treatment of coagulation disorders due to faulty formation of coagulation factors II, VII, IX, and X caused by deficiency or interference in the activity of vitamin K.¹⁷ It has a long duration of action as vitamin K is cycled in the body,⁶ and a wide therapeutic index as large doses can be tolerated.^9,18 Patients should have their prothrombin time monitored during therapy and healthcare professionals should be aware of the increased risk of hypersensitivity reactions with parenteral administration.¹⁸

Mechanism of action

Vitamin K is a cofactor of gamma-carboxylase.^7,8 Gamma carboxylase attaches carboxylic acid functional groups to glutamate, allowing precursors of factors II, VII, IX, and X to bind calcium ions.⁶ Binding of calcium ions converts these clotting factors to their active form, which are then secreted from hepatocytes into the blood, restoring normal clotting function.¹⁸

Vitamin K may also carboxylate matrix proteins in chondrocytes, inhibiting calcification of joints, and may increase type II collagen.¹⁰ The role of vitamin K in osteroarthritis,¹⁰ bone density,¹¹ and vascular calcification¹² is currently under investigation.

Target	Actions	Organism
AVitamin K-dependent gamma-carboxylase	substrate inducer cofactor	Humans
UOsteocalcin	agonist	Humans

Absorption

A 4 µg oral dose of phylloquinone is 13% ± 9% bioavailable, with a T_max of 4.7 ± 0.8 hours.⁷ 1.5 ± 0.8 nmol is found in the plasma compartment, and 3.6 ± 3.4 nmol is found in the second compartment.⁷

A 10 mg intramuscular phylloquinone dose is 89.2% ± 25.4% bioavailable.¹⁴ The same dose reaches a mean C_max of 67 ± 30 ng/mL, with a mean T_max of 9.2 ± 6.6 hours, and an AUC of 1700 ± 500 h*ng/mL.¹⁴

A 10 mg intravenous phylloquinone dose has a mean AUC of 1950 ± 450 h*ng/mL.¹⁴

Volume of distribution

The steady state volume of distribution of phylloquinone is 20 ± 6 L in subjects who are also taking phenprocoumon therapy.¹⁵

Protein binding

Not Available

Metabolism

Phylloquinone's phytyl side chain is omega hydroxylated by CYP4F2.⁵ The side chain is then cleaved to 5 or 7 carbons long, and then glucuronidated prior to elimination.^1,2,3,4

Vitamin Ks in general undergo a cycle of reduction to vitamin K hydroquinone by vitamin K epoxide reductase (VKOR), oxidation to vitamin K epoxide by gamma-glutamyl carboxylase, and converted back to vitamin K by VKOR.⁶

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Phylloquinone

Route of elimination

Intravenous phylloquinone is 36% eliminated in the feces in 5 days and 22% recovered in urine in 3 days.^1,13

Half-life

Intravenous phylloquinone has an initial half life of 22 minutes, followed by a half life of 125 minutes.¹

Clearance

Intravenous phylloquinone is 90% cleared in 2 hours, and 99% cleared in 8 hours.^1,13 A 10 mg intravenous dose of phylloquinone has a mean clearance of 91 ± 24 mL/min.¹⁴

Adverse Effects

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Toxicity

High doses of vitamin K1 are not associated with toxicity.⁶ Intravenous administration has been associated with an increased risk of toxicity.⁹ These patients should be treated with symptomatic and supportive measures.

The intravenous LD₅₀ in mice is 1170 mg/kg and the oral LD₅₀ is >24180 mg/kg.¹⁸

Pathways

Pathway	Category
Enoxaparin Action Pathway	Drug action
Fondaparinux Action Pathway	Drug action
Lepirudin Action Pathway	Drug action
Alteplase Action Pathway	Drug action
Anistreplase Action Pathway	Drug action
Urokinase Action Pathway	Drug action
Phenindione Action Pathway	Drug action
Warfarin Action Pathway	Drug action
Acenocoumarol Action Pathway	Drug action
Dicumarol Action Pathway	Drug action
Argatroban Action Pathway	Drug action
Ximelagatran Action Pathway	Drug action
Tenecteplase Action Pathway	Drug action
Aminocaproic Acid Action Pathway	Drug action
Dicoumarol Action Pathway	Drug action
Phenprocoumon Action Pathway	Drug action
Heparin Action Pathway	Drug action
Ardeparin Action Pathway	Drug action
Bivalirudin Action Pathway	Drug action
Streptokinase Action Pathway	Drug action
Reteplase Action Pathway	Drug action
Tranexamic Acid Action Pathway	Drug action
Aprotinin Action Pathway	Drug action
Vitamin K Metabolism	Metabolic
Coagulation	Physiological

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Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abacavir	Phylloquinone may decrease the excretion rate of Abacavir which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Phylloquinone which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Phylloquinone which could result in a higher serum level.
Acenocoumarol	The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Phylloquinone.
Acetaminophen	Acetaminophen may decrease the excretion rate of Phylloquinone which could result in a higher serum level.

Food Interactions

No interactions found.

Products

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Product Images

International/Other Brands

Aqua-Mephyton / Konakion

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
AquaMEPHYTON	Injection, emulsion	2 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Teligent Pharma, Inc.	2018-03-07	Not applicable
AquaMEPHYTON	Injection, emulsion	10 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Teligent Pharma, Inc.	2018-03-07	Not applicable
Mephyton	Tablet	5 mg/1	Oral	Aton Pharma, Inc.	1955-09-30	2014-05-31
Mephyton	Tablet	5 mg/1	Oral	Bausch Health US LLC	2013-03-19	Not applicable
Mephyton	Tablet	5 mg/1	Oral	Rebel Distributors	1955-09-30	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Phytonadione	Tablet	5 mg/1	Oral	Cipla USA., Inc.	2023-12-01	Not applicable
Phytonadione	Tablet	5 mg/1	Oral	Northstar Rx Llc.	2022-03-22	Not applicable
Phytonadione	Injection, emulsion	1 mg/0.5mL	Parenteral	General Injectables & Vaccines, Inc	2014-01-06	2023-08-31
Phytonadione	Tablet	5 mg/1	Oral	ScieGen Pharmaceuticals Inc	2023-07-28	Not applicable
Phytonadione	Injection, emulsion	1 mg/0.5mL	Parenteral	General Injectables & Vaccines	2013-02-13	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
KONAKION MM INJECTION 10 mg/ml	Injection	10 mg/ml	Intravenous	ROCHE SINGAPORE PTE. LTD.	1996-01-27	Not applicable
KONAKION MM PAEDIATRIC INJECTION 2 mg/0.2 ml	Injection	2 mg/0.2ml	Intramuscular; Intravenous	ROCHE SINGAPORE PTE. LTD.	1997-07-23	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Adeks - Dps	Phylloquinone (0.1 mg / mL) + Ascorbic acid (45 mg / mL) + Beta carotene (1 mg / mL) + Biotin (15 mcg / mL) + Cyanocobalamin (4 mcg / mL) + Nicotinamide (6 mg / mL) + Panthenol (3 mg / mL) + Pyridoxine hydrochloride (0.6 mg / mL) + Riboflavin (0.6 mg / mL) + Thiamine (0.5 mg / mL) + Vitamin A palmitate (1500 unit / mL) + Vitamin D (400 unit / mL) + Vitamin E (40 unit / mL) + Zinc sulfate (5 mg / mL)	Solution / drops	Oral	Axcan Pharma	1995-12-31	2007-10-01
Adeks Tablets	Phylloquinone (0.15 mg) + Ascorbic acid (60 mg) + Beta carotene (3 mg) + Biotin (50 mcg) + Cholecalciferol (400 unit) + Cyanocobalamin (12 mcg) + Folic acid (0.2 mg) + Niacin (10 mg) + Calcium pantothenate (10 mg) + Pyridoxine (1.5 mg) + Riboflavin (1.3 mg) + Thiamine (1.2 mg) + Vitamin A palmitate (4000 unit) + Vitamin E (150 unit) + Zinc gluconate (7.5 mg)	Tablet	Oral	Axcan Pharma	1998-01-20	2011-04-20
Adult Infuvite Multiple Vitamins	Phylloquinone (150 ug/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin-5'-phosphate sodium salt dihydrate (3.6 mg/10mL) + Folic acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)	Injection, solution	Intravenous	Sandoz Inc	2005-05-18	Not applicable
Adult Infuvite Multiple Vitamins	Phylloquinone (150 ug/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin-5'-phosphate sodium salt dihydrate (3.6 mg/10mL) + Folic acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)	Injection, solution	Intravenous	Sandoz Inc	2005-05-18	Not applicable
Adult Infuvite Multiple Vitamins	Phylloquinone (150 ug/10mL) + Ascorbic acid (200 mg/10mL) + Biotin (60 ug/10mL) + Cholecalciferol (200 [iU]/10mL) + Cyanocobalamin (5 ug/10mL) + Dexpanthenol (15 mg/10mL) + Riboflavin-5'-phosphate sodium salt dihydrate (3.6 mg/10mL) + Folic acid (600 ug/10mL) + Nicotinamide (40 mg/10mL) + Pyridoxine hydrochloride (6 mg/10mL) + Thiamine hydrochloride (6 mg/10mL) + Vitamin A palmitate (3300 [iU]/10mL) + alpha-Tocopherol acetate (10 [iU]/10mL)	Injection, solution	Intravenous	Sandoz Inc	2003-06-16	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Phytonadione	Phylloquinone (10 mg/1mL)	Injection, emulsion	Parenteral	Square Pharmaceuticals Ltd.	2018-04-10	Not applicable
Phytonadione	Phylloquinone (1 mg/0.5mL)	Injection, emulsion	Parenteral	Square Pharmaceuticals Ltd.	2018-04-10	Not applicable
Vitalipid N	Phylloquinone (20 ug/1mL) + DL-alpha-Tocopherol (0.7 [iU]/1mL) + Ergocalciferol (40 [iU]/1mL) + Vitamin A palmitate (230 [iU]/1mL)	Emulsion	Intravenous	Fresenius Kabi USA, LLC	2023-08-18	Not applicable
Vitalipid N	Phylloquinone (20 ug/1mL) + DL-alpha-Tocopherol (0.7 [iU]/1mL) + Ergocalciferol (40 [iU]/1mL) + Vitamin A palmitate (230 [iU]/1mL)	Emulsion	Intravenous	Fresenius Kabi USA, LLC	2023-08-18	Not applicable
Vitalipid N	Phylloquinone (15 ug/1mL) + DL-alpha-Tocopherol (1 [iU]/1mL) + Ergocalciferol (20 [iU]/1mL) + Vitamin A palmitate (330 [iU]/1mL)	Emulsion	Intravenous	Fresenius Kabi USA, LLC	2023-08-18	Not applicable

Chemical Identifiers

UNII: S5Z3U87QHF
CAS number: 84-80-0
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[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)C2=C(C=CC=C2)C1=O

References

Synthesis Reference

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

US5744624

General References

Barkhan P, Shearer MJ: Metabolism of vitamin K1 (phylloquinone) in man. Proc R Soc Med. 1977 Feb;70(2):93-6. [Article]
McBurney A, Shearer MJ, Barkhan P: Preparative isolation and characterization of the urinary aglycones of vitamin K1 (phylloquinone in man. Biochem Med. 1980 Dec;24(3):250-67. doi: 10.1016/0006-2944(80)90020-4. [Article]
Shearer MJ, Fu X, Booth SL: Vitamin K nutrition, metabolism, and requirements: current concepts and future research. Adv Nutr. 2012 Mar 1;3(2):182-95. doi: 10.3945/an.111.001800. [Article]
Turck D, Bresson JL, Burlingame B, Dean T, Fairweather-Tait S, Heinonen M, Hirsch-Ernst KI, Mangelsdorf I, McArdle HJ, Naska A, Nowicka G, Pentieva K, Sanz Y, Siani A, Sjodin A, Stern M, Tome D, Van Loveren H, Vinceti M, Willatts P, Lamberg-Allardt C, Przyrembel H, Tetens I, Dumas C, Fabiani L, Ioannidou S, Neuhauser-Berthold M: Dietary reference values for vitamin K. EFSA J. 2017 May 22;15(5):e04780. doi: 10.2903/j.efsa.2017.4780. eCollection 2017 May. [Article]
Edson KZ, Prasad B, Unadkat JD, Suhara Y, Okano T, Guengerich FP, Rettie AE: Cytochrome P450-dependent catabolism of vitamin K: omega-hydroxylation catalyzed by human CYP4F2 and CYP4F11. Biochemistry. 2013 Nov 19;52(46):8276-85. doi: 10.1021/bi401208m. Epub 2013 Nov 7. [Article]
Imbrescia K, Moszczynski Z: Vitamin K . [Article]
Jones KS, Bluck LJ, Wang LY, Coward WA: A stable isotope method for the simultaneous measurement of vitamin K1 (phylloquinone) kinetics and absorption. Eur J Clin Nutr. 2008 Nov;62(11):1273-81. doi: 10.1038/sj.ejcn.1602859. Epub 2007 Aug 1. [Article]
Shearer MJ, Newman P: Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. J Lipid Res. 2014 Mar;55(3):345-62. doi: 10.1194/jlr.R045559. Epub 2014 Jan 31. [Article]
Ingold CJ, Sergent SR: Phytonadione (Vitamin K1) . [Article]
Chin KY: The Relationship between Vitamin K and Osteoarthritis: A Review of Current Evidence. Nutrients. 2020 Apr 25;12(5). pii: nu12051208. doi: 10.3390/nu12051208. [Article]
Weber P: Vitamin K and bone health. Nutrition. 2001 Oct;17(10):880-7. doi: 10.1016/s0899-9007(01)00709-2. [Article]
Shioi A, Morioka T, Shoji T, Emoto M: The Inhibitory Roles of Vitamin K in Progression of Vascular Calcification. Nutrients. 2020 Feb 23;12(2). pii: nu12020583. doi: 10.3390/nu12020583. [Article]
Shearer MJ, Mallinson CN, Webster GR, Barkhan P: Clearance from plasma and excretion in urine, faeces and bile of an intravenous dose of tritiated vitamin K 1 in man. Br J Haematol. 1972 May;22(5):579-88. doi: 10.1111/j.1365-2141.1972.tb05704.x. [Article]
Soedirman JR, De Bruijn EA, Maes RA, Hanck A, Gruter J: Pharmacokinetics and tolerance of intravenous and intramuscular phylloquinone (vitamin K1) mixed micelles formulation. Br J Clin Pharmacol. 1996 Jun;41(6):517-23. doi: 10.1046/j.1365-2125.1996.03847.x. [Article]
Øie S, Trenk D, Guentert TW, Mosberg H, Jähnchen E: Disposition of vitamin K1 after intravenous and oral administration to subjects on phenprocoumon therapy International Journal of Pharmaceutics. 1988 Jun 15;48(1-3):223-230. [Article]
Fieser LF: Synthesis of Vitamin K1 J Am Chem Soc. 1939 Dec 1;61(12):3467-3475. [Article]
FDA Review: Vitamin K1 Subcutaneous, Intramuscular, and Intravenous Injection [Link]
Dailymed: Phytonadione Oral Tablet [Link]
FDA Approved Drug Products: Mephyton (Phylloquinone) Oral Tablet [Link]

External Links

Human Metabolome Database: HMDB0003555
KEGG Drug: D00148
KEGG Compound: C02059
PubChem Compound: 5284607
PubChem Substance: 46504528
ChemSpider: 4447652
BindingDB: 24782
RxNav: 8308
ChEBI: 18067
ChEMBL: CHEMBL1550
ZINC: ZINC000003831332
Therapeutic Targets Database: DNC001500
PharmGKB: PA450961
PDBe Ligand: PQN
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Phytomenadione

PDB Entries

1c51 / 1jb0 / 1qzv / 2o01 / 2pps / 2wsc / 2wse / 2wsf / 3lw5 / 3pcq …

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MSDS

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Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Active Not Recruiting	Treatment	Renal Failure, Chronic Renal Failure	1
4	Completed	Other	Acute Coronary Syndrome (ACS)	1
4	Completed	Prevention	Antibiotic Side Effect	1
4	Completed	Prevention	Atrial Fibrillation	1
4	Completed	Prevention	Kidney Diseases	1

Pharmacoeconomics

Manufacturers

Eli lilly and co
Hoffmann la roche inc
Aton pharma inc
Glaxosmithkline
International medication system
Hospira inc

Packagers

Amphastar Pharmaceuticals
Apotheca Inc.
Aton Pharma Inc.
Baxter International Inc.
Bimeda Inc.
Cardinal Health
Comprehensive Consultant Services Inc.
Draxis Specialty Pharmaceuticals Inc.
Gallipot
General Injectables and Vaccines Inc.
GRB SRL
H.J. Harkins Co. Inc.
Hospira Inc.
Kaiser Foundation Hospital
Merck & Co.
Murfreesboro Pharmaceutical Nursing Supply
Neuman Distributors Inc.
PD-Rx Pharmaceuticals Inc.
Physicians Total Care Inc.
Professional Co.
Rebel Distributors Corp.
Remedy Repack
Resource Optimization and Innovation LLC
Sandoz
Southwood Pharmaceuticals
Spectrum Pharmaceuticals

Dosage Forms

Form	Route	Strength
Solution / drops	Oral
Solution	Parenteral	10.000 mg
Injection, emulsion	Intramuscular; Intravenous; Subcutaneous	10 mg/1mL
Injection, emulsion	Intramuscular; Intravenous; Subcutaneous	2 mg/1mL
Tablet, effervescent	Oral
Tablet, effervescent	Oral	2500 mg
Powder, for solution	Intravenous
Solution	Intramuscular	1000000 mg
Solution	Intramuscular	1 mg
Injection	Intramuscular; Intravenous; Subcutaneous	1 mg
Injection	Intramuscular; Intravenous	10 mg
Solution	Intramuscular	10 mg
Tablet	Oral
Syrup		100 mg/5ml
Injection	Intravenous
Solution	Intravenous; Oral	10 mg
Solution	Intravenous; Oral	10 MG/ML
Solution	Oral	10 MG/ML
Solution	Oral	2 MG/0.2ML
Solution / drops	Oral	20 MG/ML
Tablet, coated		10 MG
Solution	Intravenous; Oral	1000000 mg
Solution	Intravenous; Oral	10 mg/1ml
Solution	Intramuscular; Intravenous; Oral	2 mg/0.2ml
Injection	Intravenous	10 mg/ml
Injection	Intramuscular; Intravenous	2 mg/0.2ml
Injection	Intravenous	2 mg/0.2ml
Solution	Intramuscular; Intravenous; Oral	10 mg
Solution	Intramuscular; Intravenous; Oral	1000000 mg
Injection, solution, concentrate; kit	Intravenous
Injection, powder, lyophilized, for solution	Intravenous
Tablet	Oral	5 mg/1
Solution	Intravenous
Liquid	Intravenous
Solution	Parenteral	2.000 mg
Tablet, chewable	Oral
Kit	Oral
Powder
Injection, solution; kit	Intravenous
Injection, solution	Intravenous
Tablet, sugar coated	Oral
Tablet, film coated	Oral
Tablet, sugar coated	Oral	10 Mg
Injection, emulsion	Intramuscular; Intravenous; Subcutaneous	1 mg/0.5mL
Injection, emulsion	Intramuscular; Parenteral; Subcutaneous	1 mg/0.5mL
Injection, emulsion	Parenteral	1 mg/0.5mL
Injection, emulsion	Parenteral	10 mg/1mL
Liquid	Intramuscular	2 mg / mL
Capsule, coated	Oral
Injection
Capsule	Oral
Injection		1 MG/0.5ML
Injection, emulsion	Intramuscular	10 mg/10mg
Injection, powder, for solution	Parenteral
Injection, solution
Tablet	Oral
Injection	Intravenous	330 iu/ml
Injection, solution, concentrate	Intravenous
Injection	Intravenous	230 iu/ml
Injection, emulsion	Intravenous
Emulsion	Intravenous
Liquid	Oral
Injection	Intramuscular; Intravenous; Subcutaneous
Solution	Intramuscular; Intravenous; Subcutaneous	10 mg / mL
Emulsion	Intramuscular; Intravenous; Subcutaneous	10 mg / mL
Emulsion	Intramuscular; Intravenous; Subcutaneous	2 mg / mL
Solution	Intramuscular; Intravenous; Subcutaneous	2 mg / mL
Solution		10 mg/1ml
Injection	Intramuscular	10 mg/2ml
Injection	Intramuscular	50 mg/2ml
Injection, solution		10 MG/2ML
Injection	Parenteral	10 mg
Solution	Parenteral	10 mg
Emulsion	Intramuscular; Intravenous; Subcutaneous	10 mg
Solution	Intramuscular; Intravenous; Subcutaneous	1 mg
Injection	Intramuscular; Intravenous; Subcutaneous	10 mg
Tablet	Oral	100 mcg
Capsule
Solution		2 mg/1ml
Injection, suspension		10 mg/1ml
Injection, solution		10 mg/1ml

Prices

Unit description	Cost	Unit
Phytonadione crystal	111.13USD	g
Phytonadione liquid	66.0USD	g
Vitamin k1 liquid	35.0USD	g
Mephyton 5 mg tablet	5.95USD	tablet
Vitamin K1 Pediatric 2 mg/ml	4.79USD	ml
Vitamin K1 10 mg/ml	2.76USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Liquid

Experimental Properties

Property	Value	Source
melting point (°C)	-20 °C	PhysProp
boiling point (°C)	142.5 °C at 1.00E-03 mm Hg	PhysProp
water solubility	Insoluble in water	FDA Review: Vitamine K1

Predicted Properties

Property	Value	Source
Water Solubility	5.92e-05 mg/mL	ALOGPS
logP	8.48	ALOGPS
logP	9.7	Chemaxon
logS	-6.9	ALOGPS
pKa (Strongest Basic)	-7.2	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	34.14 Å²	Chemaxon
Rotatable Bond Count	14	Chemaxon
Refractivity	142.96 m³·mol^-1	Chemaxon
Polarizability	55.92 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.8941
Caco-2 permeable	+	0.7993
P-glycoprotein substrate	Substrate	0.6643
P-glycoprotein inhibitor I	Inhibitor	0.8581
P-glycoprotein inhibitor II	Inhibitor	0.9503
Renal organic cation transporter	Non-inhibitor	0.7232
CYP450 2C9 substrate	Non-substrate	0.7852
CYP450 2D6 substrate	Non-substrate	0.827
CYP450 3A4 substrate	Substrate	0.6854
CYP450 1A2 substrate	Inhibitor	0.9107
CYP450 2C9 inhibitor	Inhibitor	0.8949
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Inhibitor	0.8994
CYP450 3A4 inhibitor	Non-inhibitor	0.8309
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.7542
Ames test	Non AMES toxic	0.8945
Carcinogenicity	Non-carcinogens	0.9183
Biodegradation	Not ready biodegradable	0.9051
Rat acute toxicity	1.1603 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.5675
hERG inhibition (predictor II)	Inhibitor	0.5

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
GC-MS Spectrum - GC-MS	GC-MS	splash10-002r-2930000000-2b32596edebbe7e02cf7
GC-MS Spectrum - GC-MS (1 TMS)	GC-MS	splash10-0002-1290000000-fa752c2db990f115c3c6
GC-MS Spectrum - GC-MS (2 TMS)	GC-MS	splash10-0002-8269080000-4bdc9b3a41d7d08b7265
GC-MS Spectrum - GC-MS (2 TMS)	GC-MS	splash10-0002-7379080000-ba90762b738ee84b3151
GC-MS Spectrum - GC-MS (2 TMS)	GC-MS	splash10-014i-6749020000-c4e58ef0e538e224dad4
GC-MS Spectrum - GC-MS (2 TMS)	GC-MS	splash10-0g4i-3149020000-ad93d4a26002eefa74ce
GC-MS Spectrum - GC-MS (2 TMS)	GC-MS	splash10-00xr-5397040000-221a2f93d46494325e33
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-000i-6895400000-254b168b019b1fc92c97
GC-MS Spectrum - EI-B	GC-MS	splash10-0udl-9740400000-e47d11ed7b15a667d611
GC-MS Spectrum - EI-B	GC-MS	splash10-0udi-2540900000-d08585615fbc2418786a
GC-MS Spectrum - GC-MS	GC-MS	splash10-002r-2930000000-2b32596edebbe7e02cf7
GC-MS Spectrum - GC-MS	GC-MS	splash10-0002-1290000000-fa752c2db990f115c3c6
GC-MS Spectrum - GC-MS	GC-MS	splash10-0002-8269080000-4bdc9b3a41d7d08b7265
GC-MS Spectrum - GC-MS	GC-MS	splash10-0002-7379080000-ba90762b738ee84b3151
GC-MS Spectrum - GC-MS	GC-MS	splash10-014i-6749020000-c4e58ef0e538e224dad4
GC-MS Spectrum - GC-MS	GC-MS	splash10-0g4i-3149020000-ad93d4a26002eefa74ce
GC-MS Spectrum - GC-MS	GC-MS	splash10-00xr-5397040000-221a2f93d46494325e33
GC-MS Spectrum - GC-MS	GC-MS	splash10-002r-2930000000-2b32596edebbe7e02cf7
GC-MS Spectrum - GC-MS	GC-MS	splash10-0002-1290000000-fa752c2db990f115c3c6
GC-MS Spectrum - GC-MS	GC-MS	splash10-0002-8269080000-4bdc9b3a41d7d08b7265
GC-MS Spectrum - GC-MS	GC-MS	splash10-0002-7379080000-ba90762b738ee84b3151
GC-MS Spectrum - GC-MS	GC-MS	splash10-014i-6749020000-c4e58ef0e538e224dad4
GC-MS Spectrum - GC-MS	GC-MS	splash10-0g4i-3149020000-ad93d4a26002eefa74ce
GC-MS Spectrum - GC-MS	GC-MS	splash10-00xr-5397040000-221a2f93d46494325e33
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0udi-5395600000-9bcbc98a3fcb8ca4bb02
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0002-0000900000-f445698f78f0a7176841
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0911300000-c79d3b8a43aa9eed3420
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0abi-9565100000-7bf23ac1c3eb5e22e5fa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-0944700000-182eb93f951204096fee
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0abl-9771200000-2efeb0fd26b2ae27a7c3
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	237.4831176	predicted	DarkChem Lite v0.1.0
[M-H]-	237.7804176	predicted	DarkChem Lite v0.1.0
[M-H]-	240.9278176	predicted	DarkChem Lite v0.1.0
[M-H]-	245.3295176	predicted	DarkChem Lite v0.1.0
[M-H]-	215.58968	predicted	DeepCCS 1.0 (2019)
[M+H]+	237.1698176	predicted	DarkChem Lite v0.1.0
[M+H]+	237.6792176	predicted	DarkChem Lite v0.1.0
[M+H]+	240.8118176	predicted	DarkChem Lite v0.1.0
[M+H]+	245.1318176	predicted	DarkChem Lite v0.1.0
[M+H]+	217.98523	predicted	DeepCCS 1.0 (2019)
[M+Na]+	237.7496176	predicted	DarkChem Lite v0.1.0
[M+Na]+	237.6764176	predicted	DarkChem Lite v0.1.0
[M+Na]+	241.6418176	predicted	DarkChem Lite v0.1.0
[M+Na]+	223.89777	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Vitamin K-dependent gamma-carboxylase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Substrate
Inducer
Cofactor

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

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. [Article]
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. [Article]
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. [Article]
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. [Article]
Olson RE: The function and metabolism of vitamin K. Annu Rev Nutr. 1984;4:281-337. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Shearer MJ, Newman P: Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. J Lipid Res. 2014 Mar;55(3):345-62. doi: 10.1194/jlr.R045559. Epub 2014 Jan 31. [Article]
Imbrescia K, Moszczynski Z: Vitamin K . [Article]

Details2. Osteocalcin

Kind: Protein
Organism: Humans
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

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. [Article]
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. [Article]
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. [Article]
Askim M: [Vitamin K in the Norwegian diet and osteoporosis]. Tidsskr Nor Laegeforen. 2001 Sep 20;121(22):2614-6. [Article]
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. [Article]
Hauschka PV, Reid ML: Vitamin K dependence of a calcium-binding protein containing gamma-carboxyglutamic acid in chicken bone. J Biol Chem. 1978 Dec 25;253(24):9063-8. [Article]

Enzymes

Details1. Leukotriene-B(4) omega-hydroxylase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Not Available
Specific Function: Not Available
Gene Name: CYP4F2
Uniprot ID: P78329
Uniprot Name: Phylloquinone omega-hydroxylase CYP4F2
Molecular Weight: 59852.825 Da

References

Edson KZ, Prasad B, Unadkat JD, Suhara Y, Okano T, Guengerich FP, Rettie AE: Cytochrome P450-dependent catabolism of vitamin K: omega-hydroxylation catalyzed by human CYP4F2 and CYP4F11. Biochemistry. 2013 Nov 19;52(46):8276-85. doi: 10.1021/bi401208m. Epub 2013 Nov 7. [Article]

Details2. UbiA prenyltransferase domain-containing protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Prenyltransferase that mediates the formation of menaquinone-4 (MK-4) and coenzyme Q10. MK-4 is a vitamin K2 isoform present at high concentrations in the brain, kidney and pancreas, and is required for endothelial cell development. Mediates the conversion of phylloquinone (PK) into MK-4, probably by cleaving the side chain of phylloquinone (PK) to release 2-methyl-1,4-naphthoquinone (menadione; K3) and then prenylating it with geranylgeranyl pyrophosphate (GGPP) to form MK-4. Also plays a role in cardiovascular development independently of MK-4 biosynthesis, by acting as a coenzyme Q10 biosynthetic enzyme: coenzyme Q10, also named ubiquinone, plays an important antioxidant role in the cardiovascular system. Mediates biosynthesis of coenzyme Q10 in the Golgi membrane, leading to protect cardiovascular tissues from NOS3/eNOS-dependent oxidative stress.
Specific Function: Antioxidant activity
Gene Name: UBIAD1
Uniprot ID: Q9Y5Z9
Uniprot Name: UbiA prenyltransferase domain-containing protein 1
Molecular Weight: 36830.745 Da

References

Shearer MJ, Newman P: Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. J Lipid Res. 2014 Mar;55(3):345-62. doi: 10.1194/jlr.R045559. Epub 2014 Jan 31. [Article]

Details3. Vitamin K epoxide reductase complex subunit 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Product of

General Function: Vitamin-k-epoxide reductase (warfarin-sensitive) activity
Specific Function: Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K. Vitamin K is required for the...
Gene Name: VKORC1
Uniprot ID: Q9BQB6
Uniprot Name: Vitamin K epoxide reductase complex subunit 1
Molecular Weight: 18234.3 Da

References

Shearer MJ, Newman P: Recent trends in the metabolism and cell biology of vitamin K with special reference to vitamin K cycling and MK-4 biosynthesis. J Lipid Res. 2014 Mar;55(3):345-62. doi: 10.1194/jlr.R045559. Epub 2014 Jan 31. [Article]
Begent LA, Hill AP, Steventon GB, Hutt AJ, Pallister CJ, Cowell DC: Characterization and purification of the vitamin K1 2,3 epoxide reductases system from rat liver. J Pharm Pharmacol. 2001 Apr;53(4):481-6. doi: 10.1211/0022357011775776. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Vitamin K1

Identification

Structure for Phylloquinone (DB01022)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

Enzymes

References

References

References