(E)-phytonadione

Also known as Vitamin K1, Phytonadione, Konakion, Phytomenadione, 2-Methyl-3-[(2e)-3,7,11,15-tetramethyl-2-hexadecenyl]naphthoquinone, Phyllochinonum, trans-Phylloquinone, 2-Methyl-3-(3,7,11,15-tetramethyl-2-hexadecenyl)-1,4-naphthalenedione

Phytomenadione, also known as vitamin K1, phylloquinone, or phytonadione, is a vitamin found in food and used as a dietary supplement. It is on the World Health Organization's List of Essential Medicines.

Key facts

Drug.image: Vitamin K1.png
Drug.image_class: skin-invert-image
Drug.caption: Above: molecular structure of phytomenadione Below: 3D representation of a phytomenadione molecule
Drug.image2: Phytomenadione 3D.png
Drug.image_class2: bg-transparent
Drug.tradename: Mephyton, Hemophyt, others
Drug.DailyMedID: Phytonadione
Drug.routes_of_administration: By mouth, subcutaneous, intramuscular, intravenous
Drug.ATC_prefix: B02
Drug.ATC_suffix: BA01
Drug.legal_CA: Rx-only
Drug.legal_US: Rx-only
Drug.CAS_number: 84-80-0
Drug.PubChem: 5284607
Drug.DrugBank: DB01022
Drug.ChemSpiderID: 4447652
Drug.UNII: S5Z3U87QHF
Drug.KEGG: D00148

via Wikipedia infobox

Chemical data

Formula: C31H46O2
Molecular weight: 450.7 g/mol
IUPAC name: 2-methyl-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enyl]naphthalene-1,4-dione
SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
InChIKey: MBWXNTAXLNYFJB-NKFFZRIASA-N
XLogP: 10.9
Polar surface area: 34.1 Å²
H-bond donors: 0
H-bond acceptors: 2
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1982
Admin. routes: oral, parenteral
Indications: postmenopausal osteoporosis, cardiovascular disease, osteoporosis, intracerebral hemorrhage

via ChEMBL · EBI

Research

213 papers

Vitamin K.2006
Weekly oral vitamin K prophylaxis in Denmark.Acta paediatrica (Oslo, Norway : 1992) · 2003
Phytonadione Content in Branded Intravenous Fat Emulsions.JPEN. Journal of parenteral and enteral nutrition · 2017
The effects of topical application of phytonadione, retinol and vitamins C and E on infraorbital dark circles and wrinkles of the lower eyelids.Journal of cosmetic dermatology · 2004
Unexpected roles of plastoglobules (plastid lipid droplets) in vitamin K1 and E metabolism.Current opinion in plant biology · 2015

via PubMed

Wikidata facts

Has part: carbon
Mass: 450.35
Has use: medication

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found in taxon: Cucumis sativus
chemical formula: C₃₁H₄₆O₂
isomeric SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)C/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C
canonical SMILES: CC1=C(C(=O)C2=CC=CC=C2C1=O)CC=C(C)CCCC(C)CCCC(C)CCCC(C)C
subject has role: primary metabolite
melting point: -20
Commons category: Phylloquinone
defined daily dose: 20
legal status (medicine): boxed warning
characteristic of: vitamin K

Sources (7)

via Wikidata · CC0

~4 min read

Encyclopedic overview

10 sections

Contents

Terminology
Medical uses
Chemistry
Biological function
Animals
Plants and cyanobacteria
Biosynthesis
Veterinary uses
References
External links

It is used to treat certain bleeding disorders, including warfarin overdose, vitamin K deficiency, and obstructive jaundice. Use is typically recommended by mouth, intramuscular injection or injection under the skin. When given by injection benefits are seen within two hours. It is also recommended for preventing and treating vitamin K deficiency bleeding in infants. Many countries in the world choose intramuscular injections in newborn to keep them safe from vitamin K deficiency bleeding. It is considered a safe treatment and saves many children from death and severe neurologic deficit every year.

Excerpted from Wikipedia’s “(E)-phytonadione” article, available under the CC BY-SA 4.0 licence.

Gallery (2)

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