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MENADIONE Drug Record

  • Summary
  • Interactions
  • Claims
  • MENADIONE chembl:CHEMBL590 Approved

    Alternate Names:

    MENADIONE
    MENAPHTHENE
    MENAPHTHONE
    NSC-4170
    KAPPAXIN
    VITAMIN K 3
    KAYQUINONE
    KOLKLOT
    MITENON
    KARCON
    KANONE
    PANOSINE
    2-METHYL-1,4-NAFTOCHINON
    2-METHYL-1,4-NAPHTHALENDIONE
    MNQ
    KAERGONA
    VITAMIN K3
    KLOTTONE
    KAYKOT
    K-THROMBYL
    AQUAKAY
    JUVA-K
    AQUINONE
    MENAQUINONE O
    2-METHYL-1,4-NAPHTHALENEDIONE
    KAPPAXAN
    MITENONE
    K-VITAN
    KATIV-G
    MENAQUINONE
    SYNKAY
    KAYKLOT
    VITAMIN K0
    2-METHYL-1,4-NAPHTHOQUINONE
    KOAXIN
    2-METHYL-1,4-NAPHTHOCHINON
    KIPCA-OIL SOLUBLE
    KAREON
    MENAPHTONE
    2-METHYL-1,4-NAPHTHODIONE
    KAYNONE
    MENAPHTHON
    PROKAYVIT
    3-METHYL-1,4-NAPHTHOQUINONE
    VITAMIN K3: 1,4-DIHYDRO-1,4-DIOXO-2-METHYLNAPHTHALENE
    THYLOQUINONE
    2-METHYL-1,4-DIHYDRONAPHTHALENE-1,4-DIONE
    MENADION
    KIPCA
    HEMODAL
    pubchem.compound:4055
    chembl:CHEMBL590
    rxcui:6728
    chemidplus:58-27-5
    drugbank:00170

    Drug Info:

    Drug Class antifibrinolytic agents
    Year of Approval approved before 1982
    FDA Approval approved
    Drug Class Small Molecule
    Drug Indications for reducing EGFR-inhibitor-induced dermatological side effects
    (1 More Sources)

    Publications:

    Ip et al., 2000, Schisandrin B protects against menadione-induced hepatotoxicity by enhancing DT-diaphorase activity., Mol. Cell. Biochem.
    Chiou et al., 1999, DT-diaphorase protects against menadione-induced oxidative stress., Toxicology
    Munday et al., 1999, Effect of butylated hydroxyanisole on the toxicity of 2-hydroxy-1,4-naphthoquinone to rats., Chem. Biol. Interact.
    Munday et al., 1999, Effect of inducers of DT-diaphorase on the toxicity of 2-methyl- and 2-hydroxy-1,4-naphthoquinone to rats., Chem. Biol. Interact.
    Kishi et al., 2002, Effect of dicumarol, a Nad(P)h: quinone acceptor oxidoreductase 1 (DT-diaphorase) inhibitor on ubiquinone redox cycling in cultured rat hepatocytes., Free Radic. Res.
    Berkessel et al., 2007, Highly enantioselective epoxidation of 2-methylnaphthoquinone (vitamin K3) mediated by new cinchona alkaloid phase-transfer catalysts., Chemistry
    Oldenburg et al., Vitamin K epoxide reductase complex subunit 1 (VKORC1): the key protein of the vitamin K cycle., Antioxid. Redox Signal.
    Stafford, 2005, The vitamin K cycle., J. Thromb. Haemost.
    Imming et al., 2006, Drugs, their targets and the nature and number of drug targets., Nat Rev Drug Discov
    Overington et al., 2006, How many drug targets are there?, Nat Rev Drug Discov
    Wang et al., 1995, The growth inhibitory effects of vitamins K and their actions on gene expression., Hepatology
    Presnell et al., 2002, The vitamin K-dependent carboxylase., Thromb. Haemost.
    Coelho Cerqueira E et al., 2011, Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO., Bioorg Med Chem
    Milgrom et al., 2007, Loss of vacuolar proton-translocating ATPase activity in yeast results in chronic oxidative stress., J. Biol. Chem.
    McCarthy et al., 1989, Retinoid-induced hemorrhaging and bone toxicity in rats fed diets deficient in vitamin K., Toxicol. Appl. Pharmacol.
    Casper et al., 1989, Evaluation of vitamin K3 feed additive for prevention of sweet clover disease., J. Vet. Diagn. Invest.
    Lee et al., 1999, Advantages of calcium green-1 over other fluorescent dyes in measuring cytosolic calcium in platelets., Anal. Biochem.
    Szejtli et al., 1983, Preparation, properties and biological activity of beta-cyclodextrin inclusion complex of menadione., Pharmazie
    Kwiek et al., 2004, Kinetic mechanism of quinone oxidoreductase 2 and its inhibition by the antimalarial quinolines., Biochemistry
    Celli et al., 2006, NRH:quinone oxidoreductase 2 (NQO2) catalyzes metabolic activation of quinones and anti-tumor drugs., Biochem. Pharmacol.
    Boutin et al., 2005, Quinone reductase 2 substrate specificity and inhibition pharmacology., Chem. Biol. Interact.
    Foster et al., 1999, Crystal structure of human quinone reductase type 2, a metalloflavoprotein., Biochemistry
    Long et al., 2002, Disruption of dihydronicotinamide riboside:quinone oxidoreductase 2 (NQO2) leads to myeloid hyperplasia of bone marrow and decreased sensitivity to menadione toxicity., J. Biol. Chem.
    Mallis et al., Irreversible thiol oxidation in carbonic anhydrase III: protection by S-glutathiolation and detection in aging rats., Biol. Chem.
    Chai et al., 1994, Protein S-thiolation in hepatocytes stimulated by t-butyl hydroperoxide, menadione, and neutrophils., Arch. Biochem. Biophys.
  • MENADIONE   PROZ

    Interaction Score: 6.62

    Interaction Types & Directionality:
    activator (activating)

    Interaction Info:

    PMIDs:
    17016423 17139284


    Sources:
    TEND

  • MENADIONE   VKORC1L1

    Interaction Score: 6.62

    Interaction Types & Directionality:
    cofactor (activating)

    Interaction Info:
    Novel drug target Established target
    Trial Name topical menadione lotion

    PMIDs:
    16677080 16102054 17016423 17139284


    Sources:
    TdgClinicalTrial TEND

  • MENADIONE   GGCX

    Interaction Score: 2.76

    Interaction Types & Directionality:
    cofactor (activating)

    Interaction Info:
    Trial Name topical menadione lotion
    Novel drug target Established target

    PMIDs:
    16102054 7657295 12083499


    Sources:
    TdgClinicalTrial TEND

  • MENADIONE   VKORC1

    Interaction Score: 1.32

    Interaction Types & Directionality:
    cofactor (activating)

    Interaction Info:
    Trial Name topical menadione lotion
    Novel drug target Established target

    PMIDs:
    16677080 16102054 17016423 17139284


    Sources:
    TdgClinicalTrial TEND

  • MENADIONE   PROS1

    Interaction Score: 1.1

    Interaction Types & Directionality:
    activator (activating)

    Interaction Info:

    PMIDs:
    12033454 8161215


    Sources:
    TEND

  • MENADIONE   PROC

    Interaction Score: 1.1

    Interaction Types & Directionality:
    activator (activating)

    Interaction Info:

    PMIDs:
    17016423 17139284 17215245


    Sources:
    TEND

  • MENADIONE   NQO2

    Interaction Score: 0.88

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    15078100 16765324 15733542 10433694 12351651


    Sources:
    TEND

  • MENADIONE   NQO1

    Interaction Score: 0.63

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    10939639 10614691 10190578 10654840 12069105


    Sources:
    TEND

  • MENADIONE   F9

    Interaction Score: 0.55

    Interaction Types & Directionality:
    activator (activating)

    Interaction Info:

    PMIDs:
    17348045


    Sources:
    TEND

  • MENADIONE   F2

    Interaction Score: 0.46

    Interaction Types & Directionality:
    activator (activating)

    Interaction Info:

    PMIDs:
    2922761 2484931 10469489 7657295 6867080


    Sources:
    TEND

  • MENADIONE   AOX1

    Interaction Score: 0.44

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    TTD

  • MENADIONE   F10

    Interaction Score: 0.32

    Interaction Types & Directionality:
    activator (activating)

    Interaction Info:

    PMIDs:
    17016423 17139284


    Sources:
    TEND

  • MENADIONE   MAOA

    Interaction Score: 0.17

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    22071524


    Sources:
    DTC

  • MENADIONE   MAOB

    Interaction Score: 0.1

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    22071524


    Sources:
    DTC

  • MENADIONE   HBB

    Interaction Score: 0.08

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   BLM

    Interaction Score: 0.02

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   PPARD

    Interaction Score: 0.02

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   ATXN2

    Interaction Score: 0.01

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   TP53

    Interaction Score: 0.01

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   ALDH1A1

    Interaction Score: 0.01

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   MAPT

    Interaction Score: 0.01

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   VDR

    Interaction Score: 0.0

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   CYP2C19

    Interaction Score: 0.0

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   CYP1A2

    Interaction Score: 0.0

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   CYP2D6

    Interaction Score: 0.0

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   NFE2L2

    Interaction Score: 0.0

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   AR

    Interaction Score: 0.0

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • MENADIONE   EHMT2

    Interaction Score: 0.0

    Interaction Types & Directionality:
    n/a

    Interaction Info:

    PMIDs:
    None found


    Sources:
    DTC

  • TEND: MENADIONE

    • Version: 01-August-2011

    Alternate Names:
    MENADIONE Primary Drug Name

    Drug Info:
    Year of Approval approved before 1982
    Drug Class antifibrinolytic agents

    Publications:

  • TdgClinicalTrial: MENADIONE

    • Version: January-2014

    Alternate Names:

    Drug Info:
    Drug Indications for reducing EGFR-inhibitor-induced dermatological side effects
    Drug Class Small Molecule
    FDA Approval approved

    Publications:

  • DTC: MENADIONE

    • Version: 02-September-2020

    Alternate Names:
    CHEMBL590 ChEMBL Drug ID

    Drug Info:

    Publications:
    Coelho Cerqueira E et al., 2011, Molecular insights into human monoamine oxidase (MAO) inhibition by 1,4-naphthoquinone: evidences for menadione (vitamin K3) acting as a competitive and reversible inhibitor of MAO., Bioorg Med Chem

  • TTD: Menadione

    • Version: 2020.06.01

    Alternate Names:
    D03GET TTD Drug ID

    Drug Info:

    Publications:

  • ChemblDrugs: chembl:CHEMBL590

    • Version: ChEMBL_27

    Alternate Names:

    Drug Info:

    Publications:

Disclaimer: This resource is intended for purely research purposes. It should not be used for emergencies or medical or professional advice.

A finding of a drug-gene interaction or potentially druggable category does not necessarily indicate effectiveness (or lack thereof) of any drug or treatment regimen. A finding of no interaction or no potentially druggable category does not necessarily indicate lack of effectiveness of any drug or treatment regimen. Drug-gene interactions or potentially druggable categories are not presented in ranked order of potential or predicted efficacy.

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DGIdb (v4.2.0 - sha1 afd9f30b) • Last updated 2020-10-21