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

Details

Stereochemistry ACHIRAL
Molecular Formula C11H8O2
Molecular Weight 172.1804
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MENADIONE

SMILES

CC1=CC(=O)c2ccccc2C1=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

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

-2.51855995E11
Primary
MENADIONE

Approved Use

Menadione Indications: severe hypoprothrombinaemia

Launch Date

-2.51855995E11
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
Role of vitamin K and vitamin K-dependent proteins in vascular calcification.
2001
Content of phylloquinone and menaquinone in the tissues of mummichog Fundulus heteroclitus fed diets containing different forms of vitamin K.
2001 Apr
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
Crossiella gen. nov., a new genus related to Streptoalloteichus.
2001 Jul
Planomicrobium koreense gen. nov., sp. nov., a bacterium isolated from the Korean traditional fermented seafood jeotgal, and transfer of Planococcus okeanokoites (Nakagawa et al. 1996) and Planococcus mcmeekinii (Junge et al. 1998) to the genus Planomicrobium.
2001 Jul
Apoptosis/differentiation-inducing effects of vitamin K2 on HL-60 cells: dichotomous nature of vitamin K2 in leukemia cells.
2001 Jul
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
Gene discovery within the planctomycete division of the domain Bacteria using sequence tags from genomic DNA libraries.
2002
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
Effect of dicumarol, a Nad(P)h: quinone acceptor oxidoreductase 1 (DT-diaphorase) inhibitor on ubiquinone redox cycling in cultured rat hepatocytes.
2002 Apr
Difference in the metabolism of vitamin K between liver and bone in vitamin K-deficient rats.
2002 Apr
Oxidant stress induces gamma-glutamylcysteine synthetase and glutathione synthesis in human bronchial epithelial NCI-H292 cells.
2002 Apr
Roles of NapF, NapG and NapH, subunits of the Escherichia coli periplasmic nitrate reductase, in ubiquinol oxidation.
2002 Apr
Role of reactive oxygen species and NAD(P)H oxidase in alpha(1)-adrenoceptor signaling in adult rat cardiac myocytes.
2002 Apr
The function of methyl-menaquinone-6 and polysulfide reductase membrane anchor (PsrC) in polysulfide respiration of Wolinella succinogenes.
2002 Feb
Generation of oxygen free radicals in thyroid cells and inhibition of thyroid peroxidase.
2002 Feb
Fumarate respiration of Wolinella succinogenes: enzymology, energetics and coupling mechanism.
2002 Jan 17
Gordonia westfalica sp. nov., a novel rubber-degrading actinomycete.
2002 Jul
Isolation and characterization of a Gram-positive polyphosphate-accumulating bacterium.
2002 Jun
Menadione biphasically controls JNK-linked cell death in leukemia Jurkat T cells.
2002 Jun
Role of antioxidant defences in the species-specific response of isolated atria to menadione.
2002 Jun
The expression of gamma-glutamyltransferase in rat colon carcinoma cells is distinctly regulated during differentiation and oxidative stress.
2002 Mar
Saccharomonospora halophila sp. nov., a novel halophilic actinomycete isolated from marsh soil in Kuwait.
2002 Mar
Georgenia muralis gen. nov., sp. nov., a novel actinobacterium isolated from a medieval wall painting.
2002 May
Salinicoccus alkaliphilus sp. nov., a novel alkaliphile and moderate halophile from Baer Soda Lake in Inner Mongolia Autonomous Region, China.
2002 May
Shift of serum osteocalcin components between cord blood and blood at day 5 of life.
2002 Nov
Effects of redox cycling compounds on glutathione content and activity of glutathione-related enzymes in rainbow trout liver.
2002 Nov
Mechanisms for the formation of major oxidation products of adenine upon 365-nm irradiation with 2-methyl-1,4-naphthoquinone as a sensitizer.
2002 Nov 29
Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity.
2002 Nov 29
Halococcus dombrowskii sp. nov., an archaeal isolate from a Permian alpine salt deposit.
2002 Sep
Pseudonocardia spinosispora sp. nov., isolated from Korean soil.
2002 Sep
Paenibacillus koleovorans sp. nov., able to grow on the sheath of Sphaerotilus natans.
2002 Sep
2-Methyl-1,4-naphthoquinone, vitamin K(3), decreases gap-junctional intercellular communication via activation of the epidermal growth factor receptor/extracellular signal-regulated kinase cascade.
2002 Sep 1
Vitamin K(2) (menaquinone 4) reduces serum undercarboxylated osteocalcin level as early as 2 weeks in elderly women with established osteoporosis.
2003
Anthracyclines induce accumulation of iron in ferritin in myocardial and neoplastic cells: inhibition of the ferritin iron mobilization pathway.
2003 Apr
Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.
2003 Feb
Agromyces aurantiacus sp. nov., isolated from a Chinese primeval forest.
2003 Jan
Paenibacillus kribbensis sp. nov. and Paenibacillus terrae sp. nov., bioflocculants for efficient harvesting of algal cells.
2003 Jan
Chryseobacterium defluvii sp. nov., isolated from wastewater.
2003 Jan
Rhodoglobus vestalii gen. nov., sp. nov., a novel psychrophilic organism isolated from an Antarctic Dry Valley lake.
2003 Jul
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.
2003 Mar
Sequential inactivation of reactive oxygen species by combined overexpression of SOD isoforms and catalase in insulin-producing cells.
2003 Mar 15
The menD and menE homologs code for 2-succinyl-6-hydroxyl-2,4-cyclohexadiene-1-carboxylate synthase and O-succinylbenzoic acid-CoA synthase in the phylloquinone biosynthetic pathway of Synechocystis sp. PCC 6803.
2003 Mar 6
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.
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]
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
MENADIONE [EP MONOGRAPH]
Common Name English
PHYTOMENADIONE IMPURITY A [EP]
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 Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
LOINC 3129-4
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
DSLD 4178 (Number of products:1)
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
WHO-VATC QB02BA02
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
WHO-ATC B02BA02
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
EPA PESTICIDE CODE 6319
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
Code System Code Type Description
HSDB
3354
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL590
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
EPA CompTox
58-27-5
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
CAS
58-27-5
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
EVMPD
SUB03142MIG
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
MERCK INDEX
M7169
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB00170
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
RXCUI
6728
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY RxNorm
USP_CATALOG
1381006
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
MENADIONE
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
PUBCHEM
4055
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
MESH
D024483
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-372-6
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
CONCEPT Dietary Supplement
DRUG CENTRAL
1683
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
NCI_THESAURUS
C66086
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY
FDA UNII
723JX6CXY5
Created by admin on Fri Jun 25 21:18:59 UTC 2021 , Edited by admin on Fri Jun 25 21:18:59 UTC 2021
PRIMARY