DGIdb - MENADIONE Drug Record

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:

Novel drug target	Established target
Trial Name	topical menadione lotion

MENADIONE Drug Record

MENADIONE chembl:CHEMBL590 Approved

Alternate Names:

Drug Info:

Publications:

Interaction Types & Directionality: activator (activating)

Interaction Info:

PMIDs: 17016423 17139284

Sources: TEND

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

Interaction Types & Directionality: cofactor (activating)

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

PMIDs: 16102054 7657295 12083499

Sources: TdgClinicalTrial TEND

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

Interaction Types & Directionality: activator (activating)

Interaction Info:

PMIDs: 12033454 8161215

Sources: TEND

Interaction Types & Directionality: activator (activating)

Interaction Info:

PMIDs: 17016423 17139284 17215245

Sources: TEND

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 15078100 16765324 15733542 10433694 12351651

Sources: TEND

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 10939639 10614691 10190578 10654840 12069105

Sources: TEND

Interaction Types & Directionality: activator (activating)

Interaction Info:

PMIDs: 17348045

Sources: TEND

Interaction Types & Directionality: activator (activating)

Interaction Info:

PMIDs: 2922761 2484931 10469489 7657295 6867080

Sources: TEND

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Sources: TTD

Interaction Types & Directionality: activator (activating)

Interaction Info:

PMIDs: 17016423 17139284

Sources: TEND

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 22071524

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 22071524

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Interaction Types & Directionality:

activator (activating)

PMIDs:
17016423 17139284

Sources:
TEND

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

Interaction Types & Directionality:

cofactor (activating)

Interaction Info:

Trial Name topical menadione lotion

Novel drug target Established target

PMIDs:
16102054 7657295 12083499

Sources:
TdgClinicalTrial TEND

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

Interaction Types & Directionality:

activator (activating)

PMIDs:
12033454 8161215

Sources:
TEND

Interaction Types & Directionality:

activator (activating)

PMIDs:
17016423 17139284 17215245

Sources:
TEND

Interaction Types & Directionality:

n/a

PMIDs:
15078100 16765324 15733542 10433694 12351651

Sources:
TEND

Interaction Types & Directionality:

n/a

PMIDs:
10939639 10614691 10190578 10654840 12069105

Sources:
TEND

Interaction Types & Directionality:

activator (activating)

PMIDs:
17348045

Sources:
TEND

Interaction Types & Directionality:

activator (activating)

PMIDs:
2922761 2484931 10469489 7657295 6867080

Sources:
TEND

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
TTD

Interaction Types & Directionality:

activator (activating)

PMIDs:
17016423 17139284

Sources:
TEND

Interaction Types & Directionality:

n/a

PMIDs:
22071524

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
22071524

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
None found