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

Molecular Formula C11H8O2
Molecular Weight 172.1804
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

-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
Role of vitamin K and vitamin K-dependent proteins in vascular calcification.
2001
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
Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta.
2001 Jan 30
Pseudonocardia kongjuensis sp. nov., isolated from a gold mine cave.
2001 Jul
Amycolatopsis albidoflavus sp. nov.
2001 Mar
Actinopolymorpha singaporensis gen. nov., sp. nov., a novel actinomycete from the tropical rainforest of Singapore.
2001 Mar
Proposal to transfer Actinomadura carminata to a new subspecies of the genus Nonomuraea as Nonomuraea roseoviolacea subsp. carminata comb. nov.
2001 May
Revival of the genus Lentzea and proposal for Lechevalieria gen. nov.
2001 May
Generation of a proton potential by succinate dehydrogenase of Bacillus subtilis functioning as a fumarate reductase.
2001 May
The tetraheme cytochrome c NrfH is required to anchor the cytochrome c nitrite reductase (NrfA) in the membrane of Wolinella succinogenes.
2001 Nov
Gene discovery within the planctomycete division of the domain Bacteria using sequence tags from genomic DNA libraries.
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
Oxidant stress induces gamma-glutamylcysteine synthetase and glutathione synthesis in human bronchial epithelial NCI-H292 cells.
2002 Apr
Role of reactive oxygen species and NAD(P)H oxidase in alpha(1)-adrenoceptor signaling in adult rat cardiac myocytes.
2002 Apr
Purification and characterization of the complex I from the respiratory chain of Rhodothermus marinus.
2002 Dec
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
Differential lipoprotein transport pathways of K-vitamins in healthy subjects.
2002 Feb 15
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
Molecular basis of proton motive force generation: structure of formate dehydrogenase-N.
2002 Mar 8
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
Lentibacillus salicampi gen. nov., sp. nov., a moderately halophilic bacterium isolated from a salt field in Korea.
2002 Nov
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
Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells.
2002 Nov 1
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
Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults.
2003
Vitamin K(2) (menaquinone 4) reduces serum undercarboxylated osteocalcin level as early as 2 weeks in elderly women with established osteoporosis.
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
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
Redox regulation of HIF-1alpha levels and HO-1 expression in renal medullary interstitial cells.
2003 Jun
Jeotgalicoccus halotolerans gen. nov., sp. nov. and Jeotgalicoccus psychrophilus sp. nov., isolated from the traditional Korean fermented seafood jeotgal.
2003 Mar
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
Halobacillus salinus sp. nov., isolated from a salt lake on the coast of the East Sea in Korea.
2003 May
Effects of menatetrenone on the bone and serum levels of vitamin K2 (menaquinone derivatives) in osteopenia induced by phenytoin in growing rats.
2003 May
Oral administration of trans-resveratrol to guinea pigs increases cardiac DT-diaphorase and catalase activities, and protects isolated atria from menadione toxicity.
2003 May 2
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 Jun 25 21:18:59 UTC 2021
Edited
by admin
on Fri Jun 25 21:18:59 UTC 2021
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]
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
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METABOLIC ENZYME -> INHIBITOR
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