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Menadione

Catalog No. DB00170 Name DrugBank
CAS Number 58-27-5 Website http://www.ualberta.ca/
M. F. C11H8O2 Telephone (780) 492-3111
M. W. 172.18002 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 55

SYNONYMS

IUPAC name
2-methyl-1,4-dihydronaphthalene-1,4-dione
IUPAC Traditional name
menadione
Brand Name
Kappaxin
Kolklot
Panosine
Klottone
Synkavite
Synkayvite
Kayklot
Synonyms
2-Methyl-1,4-Naphthalenedione
2-Methyl-1,4-naphthoquinone
Vitamin K 3
Menaphthone
Thyloquinone
Kayquinone
Vitamin K3

DATABASE IDS

CAS Number 58-27-5
PubChem SID 46505447
PubChem CID 4055

PROPERTIES

Hydrophobicity(logP) 1.6
Solubility Insoluble

DETAILS

Description (English)
Item Information
Drug Groups approved; nutraceutical
Description A synthetic naphthoquinone without the isoprenoid side chain and biological activity, but can be converted to active vitamin K2, menaquinone, after alkylation in vivo. [PubChem]
Indication The primary known function of vitamin K is to assist in the normal clotting of blood, but it may also play a role in normal bone calcification.
Pharmacology Menadione (Vitamin K3) is a fat-soluble vitamin precursor that is converted into menaquinone in the liver. Vitamin K1 and K2 are the naturally occurring types of vitamin K. The former, which is also known as phylloquinone, is synthesized by plants and can be found in such foods as spinach, broccoli, lettuce, and soybeans. The latter, sometimes alternatively referred to as menaquinone, is primarily produced by bacteria in the anterior part of the gut and the intestines. Vitamin K3, on the other hand, is one of the many manmade versions of vitamin K. Also called menadione, this yellowish, synthetic crystalline substance is converted into the active form of the K2 vitamin inside of the animal body. While a vitamin K deficiency can be dangerous, especially to infants that may easily suffer from extensive hemorrhaging, an overdose can be as equally detrimental. Newborns that are administered too great a dosage of vitamin K3 can suffer from kernicterus, a form of severe brain damage that may produce decreased movement, loss of appetite, seizures, deafness, mental retardation, and even death. This condition is associated with an abnormally high concentration of bilirubin, a bile pigment, in the tissues of the brain, which can be caused by the presence of K3. For this reason, K3 is less often utilized medically than it was in former times.
Toxicity Menadione (vitamin K3), which is not used as a nutritional supplemental form of vitamin K for humans, has been reported to cause adverse reactions, including hemolytic anemia. Large doses have also been reported to cause brain damage.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Variable and ranges from 10% to 80%
External Links
Wikipedia
PDRhealth

REFERENCES