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=CC=CC=C2C1=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 846
Vitamin digestion and absorption 1 Target ID: map04977 Sources: http://www.drugsupdate.com/generic/view/1153/Menadione	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Vitamin K deficiency 6 Sources: http://www.drugsupdate.com/generic/view/1153/Menadione	Primary	Approved 8583	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 8583	MENADIONE Approved Use Menadione Indications: severe hypoprothrombinaemia Launch Date 1962
Allergic rhinitis 104 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3f159f62-0c66-4292-9255-e6747db6208d	Palliative	Approved 8583	MENADIONE Approved Use INDICATIONS: For temporary relief of joint pains, bruising, fatigue, abdominal discomfort, diarrhea, and hay fever.

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132 CYP1A2 2153 CYP1B1 32 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP3A5 136 CYP3A7 7 P-gp 1741	P-gp 2052	CYP1A1 151 CYP1A2 832

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23435914/	likely
CYP2C8 1117	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 2.36 uM]
CYP1A1 272	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 4.39 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 4.51 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 4.6 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 5.58 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 5.76 uM]
CYP3A7 22	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 5.92 uM]
CYP1B1 93	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 7.02 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.01 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.24 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.51 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 8.91 uM]
CYP3A5 201	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4579064/	yes [IC50 9.77 uM]
CYP1A1 272	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15603920/	yes
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15603920/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 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
eMolecules	513358	https://www.emolecules.com/cgi-bin/more?vid=513358
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

PubMed

Title	Date	PubMed
Epidermal growth factor receptor is a common mediator of quinone-induced signaling leading to phosphorylation of connexin-43: role of glutathione and tyrosine phosphatases.	2003-10-03	12874275
A novel membrane-bound respiratory complex from Desulfovibrio desulfuricans ATCC 27774.	2003-08-18	12907302
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.	2003-07	12892144
Rhodoglobus vestalii gen. nov., sp. nov., a novel psychrophilic organism isolated from an Antarctic Dry Valley lake.	2003-07	12892115
Redox regulation of HIF-1alpha levels and HO-1 expression in renal medullary interstitial cells.	2003-06	12595275
Oral administration of trans-resveratrol to guinea pigs increases cardiac DT-diaphorase and catalase activities, and protects isolated atria from menadione toxicity.	2003-05-02	12679191
Halobacillus salinus sp. nov., isolated from a salt lake on the coast of the East Sea in Korea.	2003-05	12807188
Effects of menatetrenone on the bone and serum levels of vitamin K2 (menaquinone derivatives) in osteopenia induced by phenytoin in growing rats.	2003-05	12714099
Synthesis and antifilarial evaluation of N1,Nn- xylofuranosylated diaminoalkanes.	2003-04-17	12659765
Complex II from phototrophic purple bacterium Rhodoferax fermentans displays rhodoquinol-fumarate reductase activity.	2003-04	12694200
Anthracyclines induce accumulation of iron in ferritin in myocardial and neoplastic cells: inhibition of the ferritin iron mobilization pathway.	2003-04	12644586
Sequential inactivation of reactive oxygen species by combined overexpression of SOD isoforms and catalase in insulin-producing cells.	2003-03-15	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.	2003-03-06	12615349
Jeotgalicoccus halotolerans gen. nov., sp. nov. and Jeotgalicoccus psychrophilus sp. nov., isolated from the traditional Korean fermented seafood jeotgal.	2003-03	12710632
Discriminating redox cycling and arylation pathways of reactive chemical toxicity in trout hepatocytes.	2003-03	12604835
Reactive quinones differentially regulate SAPK/JNK and p38/mHOG stress kinases.	2003-02	12626122
Agromyces aurantiacus sp. nov., isolated from a Chinese primeval forest.	2003-01	12656188
Paenibacillus kribbensis sp. nov. and Paenibacillus terrae sp. nov., bioflocculants for efficient harvesting of algal cells.	2003-01	12656187
Chryseobacterium defluvii sp. nov., isolated from wastewater.	2003-01	12656158
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
Purification and characterization of the complex I from the respiratory chain of Rhodothermus marinus.	2002-12	12678433
Mechanisms for the formation of major oxidation products of adenine upon 365-nm irradiation with 2-methyl-1,4-naphthoquinone as a sensitizer.	2002-11-29	12444632
Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity.	2002-11-29	12351651
Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells.	2002-11-01	12414654
Lentibacillus salicampi gen. nov., sp. nov., a moderately halophilic bacterium isolated from a salt field in Korea.	2002-11	12508866
Shift of serum osteocalcin components between cord blood and blood at day 5 of life.	2002-11	12409510
Effects of redox cycling compounds on glutathione content and activity of glutathione-related enzymes in rainbow trout liver.	2002-11	12379427
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.	2002-09-01	12208742
Halococcus dombrowskii sp. nov., an archaeal isolate from a Permian alpine salt deposit.	2002-09	12361290
Pseudonocardia spinosispora sp. nov., isolated from Korean soil.	2002-09	12361262
Paenibacillus koleovorans sp. nov., able to grow on the sheath of Sphaerotilus natans.	2002-09	12361261
Gordonia westfalica sp. nov., a novel rubber-degrading actinomycete.	2002-07	12148617
Isolation and characterization of a Gram-positive polyphosphate-accumulating bacterium.	2002-06	12469295
Menadione biphasically controls JNK-linked cell death in leukemia Jurkat T cells.	2002-06	12215205
Role of antioxidant defences in the species-specific response of isolated atria to menadione.	2002-06	12106891
Georgenia muralis gen. nov., sp. nov., a novel actinobacterium isolated from a medieval wall painting.	2002-05	12054252
Salinicoccus alkaliphilus sp. nov., a novel alkaliphile and moderate halophile from Baer Soda Lake in Inner Mongolia Autonomous Region, China.	2002-05	12054239
Effect of dicumarol, a Nad(P)h: quinone acceptor oxidoreductase 1 (DT-diaphorase) inhibitor on ubiquinone redox cycling in cultured rat hepatocytes.	2002-04	12069105
Difference in the metabolism of vitamin K between liver and bone in vitamin K-deficient rats.	2002-04	12064340
Oxidant stress induces gamma-glutamylcysteine synthetase and glutathione synthesis in human bronchial epithelial NCI-H292 cells.	2002-04	11972604
Roles of NapF, NapG and NapH, subunits of the Escherichia coli periplasmic nitrate reductase, in ubiquinol oxidation.	2002-04	11967083
The expression of gamma-glutamyltransferase in rat colon carcinoma cells is distinctly regulated during differentiation and oxidative stress.	2002-03	12030384
Analysis of the differences in microbial community structures between suspended and sessile microorganisms in rivers based on quinone profile.	2002-02	12469314
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.	2002-01	12659145
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

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 `Mon Mar 31 17:55:02 GMT 2025` Edited by `admin` on `Mon Mar 31 17:55:02 GMT 2025`
Record UNII	723JX6CXY5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MENADIONE

Official Name

English

KAYQUINONE

Preferred 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 [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

Classification Tree Code System Code

LIVERTOX

598