Chemical Component Summary

NamePHYLLOQUINONE
Identifiers2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
FormulaC31 H46 O2
Molecular Weight450.70
TypeNON-POLYMER
Isomeric SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC\C(C)=C\CC1=C(C)C(=O)c2ccccc2C1=O
InChIInChI=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
InChIKeyMBWXNTAXLNYFJB-NKFFZRIASA-N

Chemical Details

Formal Charge0
Atom Count79
Chiral Atom Count2
Chiral AtomsC18, C23
Bond Count80
Aromatic Bond Count6
Leaving Atomsn/a

Drug Info: DrugBank

DrugBank IDDB01022 Different stereochemistry
NamePhylloquinone
Groupsapproved
DescriptionPhylloquinone 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.
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
Brand Names
  • M.V.I. Paediatric
  • M.V.I. Pediatric
  • Mephyton
  • Multi-12/k1 Pediatric
  • Phytonadione
Affected OrganismHumans and other mammals
IndicationFor the treatment of haemorrhagic conditions in infants, antidote for coumarin anticoagulants in hypoprothrombinaemia.
PharmacologyPhylloquinone 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 actionVitamin 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.
Route of administration
  • Intramuscular
  • Intramuscular; Intravenous; Subcutaneous
  • Intramuscular; Parenteral; Subcutaneous
  • Intravenous
  • Oral
Categories
  • Antifibrinolytic Agents
  • Blood and Blood Forming Organs
  • Chemical Actions and Uses
  • Coagulants
  • Diet, Food, and Nutrition
ATC-CodeB02BA01
CAS number84-80-0
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682