Chemical Component Summary

NamePHYLLOQUINONE
SynonymsVITAMIN K1; 2-METHYL-3-PHYTYL-1,4-NAPHTHOQUINONE
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 SMILESCC1=C(C(=O)c2ccccc2C1=O)C\C=C(/C)\CCC[C@H](C)CCC[C@H](C)CCCC(C)C
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
Bond Count80
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB01022 
NamePhylloquinone
Groups
  • approved
  • investigational
DescriptionVitamin K1, also called phylloquinone or phytonadione, is a fat soluble vitamin.[L33319,L33345] Phylloquinone is a cofactor of the enzyme γ-carboxylase, which modifies and activates precursors to coagulation factors II, VII, IX, and X.[A234264,A234195,A234259] 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.[L33319] Phylloquinone has been synthesized since at least 1939,[A234384] and was approved by the FDA prior to 1955.[L33389]
Synonyms
  • Phythyl-menadion
  • Phyllochinonum
  • Phytomenadionum
  • Vitamin K
  • Phyllochinon
Brand Names
  • Phytonadione Inj 2mg/ml
  • Phytonadione Phytonadione
  • Infuvite Adult Multiple Vitamins
  • Adeks Tablets
  • Mephyton
IndicationOral 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.[L33345] 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.[L33319] 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.[L33319]
Categories
  • Blood and Blood Forming Organs
  • Coagulants
  • Diet, Food, and Nutrition
  • Diterpenes
  • Drugs that are Mainly Renally Excreted
ATC-CodeB02BA01
CAS number84-80-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Vitamin K-dependent gamma-carboxylaseMAVSAGSARTSPSSDKVQKDKAELISGPRQDSRIGKLLGFEWTDLSSWRR...unknownsubstrate,inducer,cofactor
OsteocalcinMRALTLLALLALAALCIAGQAGAKPSGAESSKGAAFVSKQEGSEVVKRPR...unknownagonist
Leukotriene-B(4) omega-hydroxylase 1MSQLSLSWLGLWPVAASPWLLLLLVGASWLLAHVLAWTYAFYDNCRRLRC...unknownsubstrate
UbiA prenyltransferase domain-containing protein 1MAASQVLGEKINILSGETVKAGDRDPLGNDCPEQDRLPQRSWRQKCASYV...unknownsubstrate
Vitamin K epoxide reductase complex subunit 1MGSTWGSPGWVRLALCLTGLVLSLYALHVKAARARDRDYRALCDVGTAIS...unknownsubstrate,product of
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

Related Resource References

Resource NameReference
PubChem5284607
ChEBICHEBI:18067
ChEMBLCHEMBL1550