U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C11H8O2
Molecular Weight 172.18
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MENADIONE

SMILES

CC1=CC(=O)C2=C(C=CC=C2)C1=O

InChI

InChIKey=MJVAVZPDRWSRRC-UHFFFAOYSA-N
InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

HIDE SMILES / InChI

Molecular Formula C11H8O2
Molecular Weight 172.18
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3f159f62-0c66-4292-9255-e6747db6208d | http://www.fda.gov/downloads/Food/IngredientsPackagingLabeling/GRAS/NoticeInventory/UCM264117

Menadione, a drug belong to class of Vitamin K, is prescribed for the treatment of hemorrhage, vitamin K deficiency, moderate to severe forms of hypoprothrombinaemia in adults and children. Menadione is a synthetic form of vitamin K, a lipid-soluble vitamin. Vitamin K is a vital cofactor for the biosynthesis of prothrombin, factor VII, IX, X, protein C and protein S. Menadione supports the functions of osteocalcin. Large doses of menadione have been reported to cause adverse outcomes including hemolytic anemia due to glucose-6-phosphate dehydrogenase deficiency, neonatal brain or liver damage, or neonatal death in some rare cases.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MENADIONE

Approved Use

The additive is used or intended for use as a nutritional supplement for the Prevention of vitamin K deficiency as follows: (1) In chicken and turkey feed at a level not to exceed 2 grams per ton of complete feed. (2) In the feed of growing and finishing swine at a level not to exceed 10 grams per ton of feed.

Launch Date

1962
Primary
MENADIONE

Approved Use

Menadione Indications: severe hypoprothrombinaemia

Launch Date

1962
Palliative
MENADIONE

Approved Use

INDICATIONS: For temporary relief of joint pains, bruising, fatigue, abdominal discomfort, diarrhea, and hay fever.
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
yes [IC50 2.36 uM]
yes [IC50 4.39 uM]
yes [IC50 4.51 uM]
yes [IC50 4.6 uM]
yes [IC50 5.58 uM]
yes [IC50 5.76 uM]
yes [IC50 5.92 uM]
yes [IC50 7.02 uM]
yes [IC50 8.01 uM]
yes [IC50 8.24 uM]
yes [IC50 8.51 uM]
yes [IC50 8.91 uM]
yes [IC50 9.77 uM]
yes
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
The genome of Mycobacterium leprae: a minimal mycobacterial gene set.
2001
Menadione induces endothelial dysfunction mediated by oxidative stress and arylation.
2001 Aug 31
Identification of a novel family of putative methyltransferases that interact with human and Drosophila presenilins.
2001 Dec 12
Clustering of isochorismate synthase genes menF and entC and channeling of isochorismate in Escherichia coli.
2001 Dec 30
Ornithinimicrobium humiphilum gen. nov., sp. nov., a novel soil actinomycete with L-ornithine in the peptidoglycan.
2001 Jan
Heterozygosity for the mouse Apex gene results in phenotypes associated with oxidative stress.
2001 Jul 15
Agreia bicolorata gen. nov., sp. nov., to accommodate actinobacteria isolated from narrow reed grass infected by the nematode Heteroanguina graminophila.
2001 Nov
The tetraheme cytochrome c NrfH is required to anchor the cytochrome c nitrite reductase (NrfA) in the membrane of Wolinella succinogenes.
2001 Nov
Sulfide oxidation in gram-negative bacteria by expression of the sulfide-quinone reductase gene of Rhodobacter capsulatus and by electron transport to ubiquinone.
2001 Sep
Paenibacillus jamilae sp. nov., an exopolysaccharide-producing bacterium able to grow in olive-mill wastewater.
2001 Sep
Lateral gene transfer and parallel evolution in the history of glutathione biosynthesis genes.
2002
Synthesis, electrochemical and spectral properties of some omega-N-quinonyl amino acids.
2002
Analysis of the differences in microbial community structures between suspended and sessile microorganisms in rivers based on quinone profile.
2002 Feb
Enzymes of dimethylsulfone metabolism and the phylogenetic characterization of the facultative methylotrophs Arthrobacter sulfonivorans sp. nov., Arthrobacter methylotrophus sp. nov., and Hyphomicrobium sulfonivorans sp. nov.
2002 Feb
Salt effects on the reactions of radical ion pairs formed by electron transfer quenching of triplet 2-methyl-1,4-naphthoquinone by amines. Optical flash photolysis and step-scan FTIR investigations.
2002 Jan
Succinate:quinone oxidoreductases from epsilon-proteobacteria.
2002 Jan 17
Fumarate respiration of Wolinella succinogenes: enzymology, energetics and coupling mechanism.
2002 Jan 17
Menadione biphasically controls JNK-linked cell death in leukemia Jurkat T cells.
2002 Jun
Classification of three airborne bacteria and proposal of Hymenobacter aerophilus sp. nov.
2002 Mar
Paenibacillus koleovorans sp. nov., able to grow on the sheath of Sphaerotilus natans.
2002 Sep
Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults.
2003
Microarray analysis of orthologous genes: conservation of the translational machinery across species at the sequence and expression level.
2003
Complex II from phototrophic purple bacterium Rhodoferax fermentans displays rhodoquinol-fumarate reductase activity.
2003 Apr
A novel membrane-bound respiratory complex from Desulfovibrio desulfuricans ATCC 27774.
2003 Aug 18
Gemmatimonas aurantiaca gen. nov., sp. nov., a gram-negative, aerobic, polyphosphate-accumulating micro-organism, the first cultured representative of the new bacterial phylum Gemmatimonadetes phyl. nov.
2003 Jul
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.
2003 Mar
Patents

Sample Use Guides

Vitamin K deficiency: Oral - 10 mg every six hours Intravenous - 1-5 ug/kg/day Severe hypoprothrombinaemia: Oral - 10 mg three to four times a day Intramuscular - 2.5-10 mg
Route of Administration: Other
In Vitro Use Guide
There was a significant decrease in electrical resistance in the brain endothelial cells, isolated from heterozygous transgenic mice relative to the brain endothelial cells, isolated from heterozygous non-transgenic mice from 1h after the administration of menadione at a concentration of 60 mg/ml.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:21:23 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:23 GMT 2023
Record UNII
723JX6CXY5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MENADIONE
EP   HSDB   INCI   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
MENADIONE [VANDF]
Common Name English
MENAPHTHONE
Common Name English
MENADIONE [USP-RS]
Common Name English
MENADIONE [USP MONOGRAPH]
Common Name English
MENADIONE [HSDB]
Common Name English
MENADIONE [INCI]
Common Name English
MENADIONE [MART.]
Common Name English
MENADIONE [ORANGE BOOK]
Common Name English
NSC-4170
Code English
MENADIONE [MI]
Common Name English
Menadione [WHO-DD]
Common Name English
PHYTOMENADIONE IMPURITY A [EP IMPURITY]
Common Name English
MENADIONE [EP MONOGRAPH]
Common Name English
2-Methyl-1,4-naphthoquinone
Systematic Name English
2-METHYLNAPHTHALENE-1,4-DIONE
Systematic Name English
VITAMIN K 3
Common Name English
VITAMIN K3
Common Name English
1,4-NAPHTHALENEDIONE, 2-METHYL
Common Name English
KAYQUINONE
Brand Name English
Classification Tree Code System Code
LIVERTOX 598
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
LOINC 3129-4
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
DSLD 4178 (Number of products:1)
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
WHO-VATC QB02BA02
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
WHO-ATC B02BA02
Created by admin on Fri Dec 15 15:21:23 GMT 2023 , Edited by admin on Fri Dec 15 15:21:23 GMT 2023
EPA PESTICIDE CODE 6319
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
Code System Code Type Description
NSC
4170
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
HSDB
3354
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL590
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID4021715
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
CAS
58-27-5
Created by admin on Fri Dec 15 15:21:23 GMT 2023 , Edited by admin on Fri Dec 15 15:21:23 GMT 2023
PRIMARY
EVMPD
SUB03142MIG
Created by admin on Fri Dec 15 15:21:23 GMT 2023 , Edited by admin on Fri Dec 15 15:21:23 GMT 2023
PRIMARY
MERCK INDEX
m7169
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB00170
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
RS_ITEM_NUM
1381006
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
RXCUI
6728
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
MENADIONE
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
PUBCHEM
4055
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
CHEBI
28869
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
MESH
D024483
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-372-6
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
CONCEPT Dietary Supplement
DRUG CENTRAL
1683
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
DAILYMED
723JX6CXY5
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
SMS_ID
100000086399
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
NCI_THESAURUS
C66086
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
FDA UNII
723JX6CXY5
Created by admin on Fri Dec 15 15:21:24 GMT 2023 , Edited by admin on Fri Dec 15 15:21:24 GMT 2023
PRIMARY
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