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

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
Inactivation of both RNA binding and aconitase activities of iron regulatory protein-1 by quinone-induced oxidative stress.	1999 Mar 5	10037708
The genome of Mycobacterium leprae: a minimal mycobacterial gene set.	2001	11532219
Content of phylloquinone and menaquinone in the tissues of mummichog Fundulus heteroclitus fed diets containing different forms of vitamin K.	2001 Apr	11508712
Electron transfer and binding of the c-type cytochrome TorC to the trimethylamine N-oxide reductase in Escherichia coli.	2001 Apr 13	11056172
Menadione induces endothelial dysfunction mediated by oxidative stress and arylation.	2001 Aug 31	11551532
Clustering of isochorismate synthase genes menF and entC and channeling of isochorismate in Escherichia coli.	2001 Dec 30	11779629
Ornithinimicrobium humiphilum gen. nov., sp. nov., a novel soil actinomycete with L-ornithine in the peptidoglycan.	2001 Jan	11211277
Characterization of enzymes participating in carbonyl reduction of 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in human placenta.	2001 Jan 30	11306090
Crossiella gen. nov., a new genus related to Streptoalloteichus.	2001 Jul	11491360
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	11491353
Pseudonocardia kongjuensis sp. nov., isolated from a gold mine cave.	2001 Jul	11491352
Apoptosis/differentiation-inducing effects of vitamin K2 on HL-60 cells: dichotomous nature of vitamin K2 in leukemia cells.	2001 Jul	11455981
Heterozygosity for the mouse Apex gene results in phenotypes associated with oxidative stress.	2001 Jul 15	11454706
Amycolatopsis albidoflavus sp. nov.	2001 Mar	11321110
Effects of modulation of tissue activities of DT-diaphorase on the toxicity of 2,3-dimethyl-1,4-naphthoquinone to rats.	2001 Mar 14	11248224
Proposal of Mycetocola gen. nov. in the family Microbacteriaceae and three new species, Mycetocola saprophilus sp. nov., Mycetocola tolaasinivorans sp. nov. and Mycetocola lacteus sp. nov., isolated from cultivated mushroom, Pleurotus ostreatus.	2001 May	11411718
Generation of a proton potential by succinate dehydrogenase of Bacillus subtilis functioning as a fumarate reductase.	2001 May	11358526
Agreia bicolorata gen. nov., sp. nov., to accommodate actinobacteria isolated from narrow reed grass infected by the nematode Heteroanguina graminophila.	2001 Nov	11760949
Paenibacillus jamilae sp. nov., an exopolysaccharide-producing bacterium able to grow in olive-mill wastewater.	2001 Sep	11594596
Lateral gene transfer and parallel evolution in the history of glutathione biosynthesis genes.	2002	12049666
Difference in the metabolism of vitamin K between liver and bone in vitamin K-deficient rats.	2002 Apr	12064340
Roles of NapF, NapG and NapH, subunits of the Escherichia coli periplasmic nitrate reductase, in ubiquinol oxidation.	2002 Apr	11967083
Analysis of the differences in microbial community structures between suspended and sessile microorganisms in rivers based on quinone profile.	2002 Feb	12469314
Succinate:quinone oxidoreductases from epsilon-proteobacteria.	2002 Jan 17	11803019
Isolation and characterization of a Gram-positive polyphosphate-accumulating bacterium.	2002 Jun	12469295
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
Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity.	2002 Nov 29	12351651
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
Microarray analysis of orthologous genes: conservation of the translational machinery across species at the sequence and expression level.	2003	12537549
Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.	2003 Feb	12626122
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
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
Halobacillus salinus sp. nov., isolated from a salt lake on the coast of the East Sea in Korea.	2003 May	12807188
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.

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

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LOINC

3129-4

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DSLD

4178 (Number of products:1)

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WHO-VATC

QB02BA02

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WHO-ATC

B02BA02

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EPA PESTICIDE CODE

6319

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Code System Code Type Description

NSC

4170

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HSDB

3354

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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

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PUBCHEM

4055

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CHEBI

28869

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MESH

D024483

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ECHA (EC/EINECS)

200-372-6

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NCI_THESAURUS

C1505

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CONCEPT

Dietary Supplement

DRUG CENTRAL

1683

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DAILYMED

723JX6CXY5

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SMS_ID

100000086399

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NCI_THESAURUS

C66086

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FDA UNII

723JX6CXY5

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ACTIVE MOIETY


					723JX6CXY5

MENADIONE

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