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Identification
Name Phytonadione
Accession Number DB01022 (APRD00464)
Type small molecule
Groups approved
Description

Phytonadione 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
2-Methyl-3-phythyl-1,4-naphthochinon
2', 3'-trans-Vitamin K1
3-Phytylmenadione
alpha-Phylloquinone
Antihemorrhagic vitamin
Phyllochinon
Phylloquinone
Phythyl-menadion (GERMAN)
Phytomenadione
Phytylmenadione
Vitamin K
Vitamin K1
First Prev Next Last
Salts Not Available
Brand names
Name Company
Aqua-Mephytin
AquaMEPHYTON
Combinal K1
K-Ject
Kativ N
Kephton
Kinadion
Konakion
Mephyton
Mono-Kay
Monodion
Synthex P
First Prev Next Last
Brand mixtures Not Available
Categories
  • Antifibrinolytic Agents
  • Vitamins (Vitamin K)
  • Vitamins
CAS number 84-80-0
Weight Average: 450.6957
Monoisotopic: 450.349780716
Chemical Formula C31H46O2
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of haemorrhagic conditions in infants, antidote for coumarin anticoagulants in hypoprothrombinaemia
Pharmacodynamics Phytonadione 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. Phytonadione 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 Phytonadione results in a relief of vitamin K deficiency symptoms which include easy bruisability, epistaxis, gastrointestinal bleeding, menorrhagia and hematuria.
Absorption Oral phytonadione is adequately absorbed from the gastrointestinal tract only if bile salts are present. After absorption, phytonadione 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 phytonadione 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 Not Available
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Hoffmann la roche inc
  • Aton pharma inc
  • Glaxosmithkline
  • International medication system
  • Hospira inc
Packagers
Dosage forms
Form Route Strength
Injection, solution Intramuscular
Injection, solution Intravenous
Injection, solution Subcutaneous
Prices
Unit description Cost Unit
Phytonadione crystal 111.13 USD g
Phytonadione liquid 66.0 USD g
Vitamin k1 liquid 35.0 USD g
Mephyton 5 mg tablet 5.95 USD tablet
Vitamin K1 Pediatric 2 mg/ml 4.79 USD ml
Vitamin K1 10 mg/ml 2.76 USD 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 -20 °C PhysProp
boiling point 142.5 °C at 1.00E-03 mm Hg PhysProp
water solubility Insoluble in water Not Available
logP 9.3 Not Available
Predicted Properties
Property Value Source
water solubility 5.92e-05 g/l 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 ChemAxon
rotatable bond count 14 ChemAxon
refractivity 142.96 ChemAxon
polarizability 55.92 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00148 Link_out
KEGG Compound C02059 Link_out
ChEBI 18067 Link_out
ChEMBL 18067 Link_out
Therapeutic Targets Database DNC001500 Link_out
PharmGKB PA450961 Link_out
Drug Product Database 243876 Link_out
RxList http://www.rxlist.com/cgi/generic3/phytonadione.htm Link_out
Drugs.com http://www.drugs.com/cdi/phytonadione.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Phytonadione Link_out
ATC Codes
  • B02BA01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (72 KB)
Interactions
Drug Interactions
Drug Interaction
Warfarin Phytonadione (vitamin K) may antagonize the anticoagulant effects of warfarin. Monitor for changes in prothrombin time if phytonadione intake (either via supplements or vitamin K-rich foods) is increased or decreased.
Food Interactions Not Available
Targets

1. Vitamin K-dependent gamma-carboxylase

Pharmacological action: yes
Actions: inducer

Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium binding gamma-carboxyglutamate (Gla) residues with the concomitant convertion of the reduced hydroquinone form of vitamin K to vitamin K epoxide

Organism class: human
UniProt ID: P38435 Link_out
Gene: GGCX Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  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
  5. Olson RE: The function and metabolism of vitamin K. Annu Rev Nutr. 1984;4:281-337. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Osteocalcin

Pharmacological action: unknown
Actions: agonist

Constitutes 1-2% of the total bone protein. It binds strongly to apatite and calcium

Organism class: human
UniProt ID: P02818 Link_out
Gene: BGLAP Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
  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
  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
  4. Askim M: [Vitamin K in the Norwegian diet and osteoporosis] Tidsskr Nor Laegeforen. 2001 Sep 20;121(22):2614-6. Pubmed
  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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19