MENADIONE

First approved in 1940

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 Search

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
Sources: http://www.drugsupdate.com/generic/view/1153/Menadione
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Complement and Coagulation Cascades 1 Target ID: WP558 Sources: http://www.drugsupdate.com/generic/view/1153/Menadione	Modulator 828
Vitamin digestion and absorption 1 Target ID: map04977 Sources: http://www.drugsupdate.com/generic/view/1153/Menadione	Modulator 828

Conditions

Condition	Modality	Highest Phase	Product
Vitamin K deficiency 6 Sources: http://www.drugsupdate.com/generic/view/1153/Menadione	Primary	Approved 8429	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
Severe hypoprothrombinaemia 1 Sources: http://www.drugsupdate.com/generic/view/1153/Menadione	Primary	Approved 8429	MENADIONE Approved Use Menadione Indications: severe hypoprothrombinaemia Launch Date 1962
Allergic rhinitis 100 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3f159f62-0c66-4292-9255-e6747db6208d	Palliative	Approved 8429	MENADIONE Approved Use INDICATIONS: For temporary relief of joint pains, bruising, fatigue, abdominal discomfort, diarrhea, and hay fever.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 110 CYP1A2 1524 CYP1B1 19 CYP2A6 707 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882 CYP3A5 73 CYP3A7 7 P-gp 1461	P-gp 1537	CYP1A1 108 CYP1A2 701

Drug as perpetrator

Target	Modality	Activity
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23435914/	likely
CYP2C8 965	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 2.36 uM]
CYP1A1 218	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 4.39 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 4.51 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 4.6 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 5.58 uM]
CYP2B6 1001	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 5.76 uM]
CYP3A7 22	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 5.92 uM]
CYP1B1 67	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 7.02 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.01 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.24 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.51 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.91 uM]
CYP3A5 130	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 9.77 uM]
CYP1A1 218	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15603920/	yes
CYP1A2 1692	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/15603920/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1537	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23435914/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28869	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28869
ChemicalBook	CB4494726	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB4494726
MolPort	MolPort-001-766-699	https://www.molport.com/shop/molecule-link/MolPort-001-766-699
Selleck Chemicals	Menadione	http://www.selleckchem.com/products/Menadione.html
ZINC	ZINC000000001677	http://zinc15.docking.org/substances/ZINC000000001677
eMolecules	513358	https://www.emolecules.com/cgi-bin/more?vid=513358

PubMed

Title	Date	PubMed
Gene discovery within the planctomycete division of the domain Bacteria using sequence tags from genomic DNA libraries.	2002	12093378
Lateral gene transfer and parallel evolution in the history of glutathione biosynthesis genes.	2002	12049666
Synthesis, electrochemical and spectral properties of some omega-N-quinonyl amino acids.	2002	12025875
Effect of dicumarol, a Nad(P)h: quinone acceptor oxidoreductase 1 (DT-diaphorase) inhibitor on ubiquinone redox cycling in cultured rat hepatocytes.	2002 Apr	12069105
Difference in the metabolism of vitamin K between liver and bone in vitamin K-deficient rats.	2002 Apr	12064340
Oxidant stress induces gamma-glutamylcysteine synthetase and glutathione synthesis in human bronchial epithelial NCI-H292 cells.	2002 Apr	11972604
Roles of NapF, NapG and NapH, subunits of the Escherichia coli periplasmic nitrate reductase, in ubiquinol oxidation.	2002 Apr	11967083
Reconstitution of coupled fumarate respiration in liposomes by incorporating the electron transport enzymes isolated from Wolinella succinogenes.	2002 Apr	11952800
Purification and characterization of the complex I from the respiratory chain of Rhodothermus marinus.	2002 Dec	12678433
Analysis of the differences in microbial community structures between suspended and sessile microorganisms in rivers based on quinone profile.	2002 Feb	12469314
Differential lipoprotein transport pathways of K-vitamins in healthy subjects.	2002 Feb 15	11960685
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	12659145
Gordonia westfalica sp. nov., a novel rubber-degrading actinomycete.	2002 Jul	12148617
Isolation and characterization of a Gram-positive polyphosphate-accumulating bacterium.	2002 Jun	12469295
Role of antioxidant defences in the species-specific response of isolated atria to menadione.	2002 Jun	12106891
The expression of gamma-glutamyltransferase in rat colon carcinoma cells is distinctly regulated during differentiation and oxidative stress.	2002 Mar	12030384
Saccharomonospora halophila sp. nov., a novel halophilic actinomycete isolated from marsh soil in Kuwait.	2002 Mar	11931168
Classification of three airborne bacteria and proposal of Hymenobacter aerophilus sp. nov.	2002 Mar	11931156
Paenibacillus chinjuensis sp. nov., a novel exopolysaccharide-producing bacterium.	2002 Mar	11931150
Major adenine products from 2-methyl-1,4-naphthoquinone-sensitized photoirradiation at 365 nm.	2002 Mar 15	11883952
Molecular basis of proton motive force generation: structure of formate dehydrogenase-N.	2002 Mar 8	11884747
Georgenia muralis gen. nov., sp. nov., a novel actinobacterium isolated from a medieval wall painting.	2002 May	12054252
Salinicoccus alkaliphilus sp. nov., a novel alkaliphile and moderate halophile from Baer Soda Lake in Inner Mongolia Autonomous Region, China.	2002 May	12054239
Lentibacillus salicampi gen. nov., sp. nov., a moderately halophilic bacterium isolated from a salt field in Korea.	2002 Nov	12508866
Shift of serum osteocalcin components between cord blood and blood at day 5 of life.	2002 Nov	12409510
Effects of redox cycling compounds on glutathione content and activity of glutathione-related enzymes in rainbow trout liver.	2002 Nov	12379427
Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells.	2002 Nov 1	12414654
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	12444632
Halococcus dombrowskii sp. nov., an archaeal isolate from a Permian alpine salt deposit.	2002 Sep	12361290
Pseudonocardia spinosispora sp. nov., isolated from Korean soil.	2002 Sep	12361262
Neocortical neurons cultured from mice with expanded CAG repeats in the huntingtin gene: unaltered vulnerability to excitotoxins and other insults.	2003	12895502
Vitamin K(2) (menaquinone 4) reduces serum undercarboxylated osteocalcin level as early as 2 weeks in elderly women with established osteoporosis.	2003	12720050
Serum markers variation consistent with autoschizis induced by ascorbic acid-menadione in patients with prostate cancer.	2003	12665684
Microarray analysis of orthologous genes: conservation of the translational machinery across species at the sequence and expression level.	2003	12537549
Complex II from phototrophic purple bacterium Rhodoferax fermentans displays rhodoquinol-fumarate reductase activity.	2003 Apr	12694200
Anthracyclines induce accumulation of iron in ferritin in myocardial and neoplastic cells: inhibition of the ferritin iron mobilization pathway.	2003 Apr	12644586
Synthesis and antifilarial evaluation of N1,Nn- xylofuranosylated diaminoalkanes.	2003 Apr 17	12659765
A novel membrane-bound respiratory complex from Desulfovibrio desulfuricans ATCC 27774.	2003 Aug 18	12907302
Paenibacillus kribbensis sp. nov. and Paenibacillus terrae sp. nov., bioflocculants for efficient harvesting of algal cells.	2003 Jan	12656187
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	12892144
Rhodoglobus vestalii gen. nov., sp. nov., a novel psychrophilic organism isolated from an Antarctic Dry Valley lake.	2003 Jul	12892115
Redox regulation of HIF-1alpha levels and HO-1 expression in renal medullary interstitial cells.	2003 Jun	12595275
Jeotgalicoccus halotolerans gen. nov., sp. nov. and Jeotgalicoccus psychrophilus sp. nov., isolated from the traditional Korean fermented seafood jeotgal.	2003 Mar	12710632
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.	2003 Mar	12604835
Sequential inactivation of reactive oxygen species by combined overexpression of SOD isoforms and catalase in insulin-producing cells.	2003 Mar 15	12633745
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	12615349
Halobacillus salinus sp. nov., isolated from a salt lake on the coast of the East Sea in Korea.	2003 May	12807188
Effects of menatetrenone on the bone and serum levels of vitamin K2 (menaquinone derivatives) in osteopenia induced by phenytoin in growing rats.	2003 May	12714099
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	12679191
Epidermal growth factor receptor is a common mediator of quinone-induced signaling leading to phosphorylation of connexin-43: role of glutathione and tyrosine phosphatases.	2003 Oct 3	12874275

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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Code System Code Type Description

NSC

4170

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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

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EPA CompTox

DTXSID4021715

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CAS

58-27-5

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EVMPD

SUB03142MIG

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MERCK INDEX

m7169

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Merck Index

DRUG BANK

DB00170

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RS_ITEM_NUM

1381006

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RXCUI

6728

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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

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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

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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

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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

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DAILYMED

723JX6CXY5

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PRIMARY

SMS_ID

100000086399

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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

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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

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					LR0F81F33L

ALDEHYDE OXIDASE

METABOLIC ENZYME -> INHIBITOR

Qualification:

IC50

Amount:

Related Record Type Details


					A034SE7857

PHYTONADIONE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

Related Record Type Details


					723JX6CXY5

MENADIONE

ACTIVE MOIETY

Details

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Drug as perpetrator