Menadione

Menadione
IUPAC name	2-methylnaphthalene-1,4-dione
Identifiers
CAS number	58-27-5
PubChem	4055
SMILES	CC1=CC(=O)C2=CC=CC=C2C1=O
Properties
Molecular formula	C11H8O2
Molar mass	172.18
Melting point	102 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

WikiDoc Resources for Menadione
Articles
Most recent articles on Menadione Most cited articles on Menadione Review articles on Menadione Articles on Menadione in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Menadione Images of Menadione Photos of Menadione Podcasts & MP3s on Menadione Videos on Menadione
Evidence Based Medicine
Cochrane Collaboration on Menadione Bandolier on Menadione TRIP on Menadione
Clinical Trials
Ongoing Trials on Menadione at Clinical Trials.gov Trial results on Menadione Clinical Trials on Menadione at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Menadione NICE Guidance on Menadione NHS PRODIGY Guidance FDA on Menadione CDC on Menadione
Books
Books on Menadione
News
Menadione in the news Be alerted to news on Menadione News trends on Menadione
Commentary
Blogs on Menadione
Definitions
Definitions of Menadione
Patient Resources / Community
Patient resources on Menadione Discussion groups on Menadione Patient Handouts on Menadione Directions to Hospitals Treating Menadione Risk calculators and risk factors for Menadione
Healthcare Provider Resources
Symptoms of Menadione Causes & Risk Factors for Menadione Diagnostic studies for Menadione Treatment of Menadione
Continuing Medical Education (CME)
CME Programs on Menadione
International
Menadione en Espanol Menadione en Francais
Business
Menadione in the Marketplace Patents on Menadione
Experimental / Informatics
List of terms related to Menadione

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Menadione is a polycyclic aromatic ketone, based on 1,4-naphthoquinone, with a 2-methyl substituent.

It was formerly sometimes called vitamin K₃, although derivatives of naphthoquinone without the sidechain in the 3-position cannot exert all the functions of the K vitamins. Menadione is a vitamin precursor of K₂ which utilizes alkylation in the liver to yield menaquinones (MK-n, n=1-13; K₂ vitamers), and hence, is better classified as a provitamin.

Despite the fact that it can serve as a precursor to various types of vitamin K, menadione is generally not used as a nutritional supplement. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to G6PD deficiency, neonatal brain or liver damage, or neonatal death in some cases. Moreover, menadione supplements have been banned by the FDA because of their high toxicity. Menadione has been used experimentally as a chemotherapic agent for cancer, ca 1945, but has lost ground to much safer, human form, vitamin K₂ vitamers. Low level menadione is still used as an inexpensive micronutrient for livestock in many countries.

Lately, menadione has been mentioned again as a treatment for cancer in conjunction with vitamin C (See "The end of cancer" by April Kirkendoll) but modern researchers and trials are investigating nontoxic K₂ vitamers such as menaquinone-4^[2] in conjunction with more comprehensive regimens.

See also

• Vitamin K

de:Menadion