Details of the Drug

General Information of Drug (ID: DMSJDTY)

Drug Name
Menadione
Synonyms
menadione; 58-27-5; Vitamin K3; 2-Methyl-1,4-naphthoquinone; Menaphthone; 2-methylnaphthalene-1,4-dione; 2-Methylnaphthoquinone; Thyloquinone; Panosine; Klottone; Kayquinone; Kappaxin; Kayklot; Kolklot; 2-Methyl-1,4-naphthalenedione; Menaphthon; Menadion; Kipca; Kanone; Mitenone; Kativ-G; Kaergona; Aquinone; Prokayvit; Mitenon; Koaxin; Kaykot; Kareon; Hemodal; Aquakay; Synkay; Karcon; K-Thrombyl; K-Vitan; Kipca-Oil Soluble; Juva-K; Vitamin K2(0); Vitamin K0; Menaquinone 0; Vitamin K 3; Menaphtone; Menadionum; 2-Methyl-1,4-naphthochinon; Usaf; Aquakay; Klottone;Koaxin; Memodol; Methylnaphthoquinone; Vicasol; Menadione semiquinone; M0373; VK3; Kappaxan (VAN); Kappaxin (TN); Kipca, oil soluble; Menadione (K3); Menadione (USP); Menadione [USAN:BAN]; Usaf ek-5185; Vitamin-K3; Methyl-1,4-naphthalenedione; Methyl-1,4-naphthoquinone; Vitamin K3 : 2-Methyl-1,4-naphthoquinone; 1,4-Naphthalenedione, 2-methyl-,radical ion(1-); 2-Methyl-1,4-naftochinon; 2-Methyl-1,4-naftochinon [Czech]; 2-Methyl-1,4-naphthochinon [German]; 2-methyl-1,4-naphthoquinone, 5; 3-Methyl-1,4-naphthoquinone; Ascorbic acid/menadione; Triglycyl-lysine-vasopressin
Indication
Disease Entry ICD 11 Status REF
Vitamin K deficiency 5B59 Approved [1]
Prostate cancer 2C82.0 Phase 2 [2]
Therapeutic Class
Vitamins
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 172.18
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption
The absorption of drug is 10-80% []
Metabolism
The drug is metabolized via the hepatic []
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Adverse drug reaction Not Available TUBGCP3 OTFOQY1M [3]
Cytology abnormal Not Available COL4A1 OTL6D1YE [3]
Cytology abnormal Not Available VCL OTPQ0JYS [3]
Investigations Not Available FN1 OTB5ZN4Q [3]
Investigations Not Available B2M OTDWN6NX [3]
Chemical Identifiers
Formula
C11H8O2
IUPAC Name
2-methylnaphthalene-1,4-dione
Canonical SMILES
CC1=CC(=O)C2=CC=CC=C2C1=O
InChI
InChI=1S/C11H8O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3
InChIKey
MJVAVZPDRWSRRC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4055
ChEBI ID
CHEBI:28869
CAS Number
58-27-5
DrugBank ID
DB00170
TTD ID
D03GET
VARIDT ID
DR01167
INTEDE ID
DR1022
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aldehyde oxidase (AOX1) TT3MOS2 AOXA_HUMAN Inhibitor [4]
Vasopressin V1 receptor (V1R) TTPFZJ1 NOUNIPROTAC Agonist [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [7]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [8]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [8]
Methylenetetrahydrofolate reductase (MTHFR) DEOXTPZ MTHR_HUMAN Substrate [9]
NADPH-dependent carbonyl reductase 1 (CBR1) DE9JFMC CBR1_HUMAN Substrate [10]
Methionine synthase reductase (MTRR) DE6NIY9 MTRR_HUMAN Substrate [11]
NADPH:quinone reductase (CRYZ) DE8RYV5 QOR_HUMAN Substrate [12]
NADPH-dependent carbonyl reductase 3 (CBR3) DEIVKZ8 CBR3_HUMAN Substrate [13]
Nitroreductase (NTR) DEPG9C0 A0A5K1UB29_SALTM Substrate [14], [15]
Sepiapterin reductase (SPR) DEJVDAT SPRE_HUMAN Substrate [16]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1) OTG2T749 CP24A_HUMAN Gene/Protein Processing [17]
1-acyl-sn-glycerol-3-phosphate acyltransferase gamma (AGPAT3) OTAUR5TG PLCC_HUMAN Gene/Protein Processing [18]
1-acylglycerol-3-phosphate O-acyltransferase ABHD5 (ABHD5) OTY829Z3 ABHD5_HUMAN Gene/Protein Processing [18]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase epsilon-1 (PLCE1) OTJISZOX PLCE1_HUMAN Gene/Protein Processing [18]
11-beta-hydroxysteroid dehydrogenase type 2 (HSD11B2) OTHF4H9U DHI2_HUMAN Gene/Protein Processing [17]
14-3-3 protein beta/alpha OTGBS3RF 1433B_HUMAN Gene/Protein Processing [18]
2-(3-amino-3-carboxypropyl)histidine synthase subunit 1 (DPH1) OT0QU3JY DPH1_HUMAN Gene/Protein Processing [18]
2-oxoglutarate and iron-dependent oxygenase domain-containing protein 3 (OGFOD3) OT3TAYTX OGFD3_HUMAN Gene/Protein Processing [18]
2-oxoglutarate dehydrogenase-like, mitochondrial (OGDHL) OT1AZK6R OGDHL_HUMAN Gene/Protein Processing [18]
2-phosphoxylose phosphatase 1 (PXYLP1) OTX8T7F6 PXYP1_HUMAN Gene/Protein Processing [18]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 002139.
2 ClinicalTrials.gov (NCT01272830) Double-Blinded Clinical Trial Using ApatoneB for Symptomatic Postoperative Total Joint Replacements. U.S. National Institutes of Health.
3 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
4 Inhibition by SKF-525A of the aldehyde oxidase-mediated metabolism of the experimental antitumour agent acridine carboxamide. Biochem Pharmacol. 1993 May 25;45(10):2159-62.
5 Evidence in hyponatremia related to inappropriate secretion of ADH that V1 receptor stimulation contributes to the increase in renal uric acid clearance. J Am Soc Nephrol. 1996 May;7(5):805-10.
6 The naphthoquinones, vitamin K3 and its structural analogue plumbagin, are substrates of the multidrug resistance linked ATP binding cassette drug transporter ABCG2. Mol Cancer Ther. 2007 Dec;6(12 Pt 1):3279-86.
7 CYP2E1 overexpression alters hepatocyte death from menadione and fatty acids by activation of ERK1/2 signaling. Hepatology. 2004 Feb;39(2):444-55.
8 Rat hepatic CYP1A1 and CYP1A2 induction by menadione. Toxicol Lett. 2005 Feb 15;155(2):253-8.
9 Purification and properties of 5,10-methylenetetrahydrofolate reductase, an iron-sulfur flavoprotein from Clostridium formicoaceticum. J Biol Chem. 1984 Sep 10;259(17):10845-9.
10 Polycyclic aromatic hydrocarbon quinones and glutathione thioethers as substrates and inhibitors of the human placental NADP-linked 15-hydroxyprostaglandin dehydrogenase. J Biol Chem. 1987 Sep 15;262(26):12448-51.
11 Differences in the efficiency of reductive activation of methionine synthase and exogenous electron acceptors between the common polymorphic variants of human methionine synthase reductase. Biochemistry. 2002 Nov 12;41(45):13378-85.
12 Role of glutathione reductase during menadione-induced NADPH oxidation in isolated rat hepatocytes. Biochem Pharmacol. 1987 Nov 15;36(22):3879-84.
13 Different functions between human monomeric carbonyl reductase 3 and carbonyl reductase 1. Mol Cell Biochem. 2008 Aug;315(1-2):113-21.
14 Purification and characterization of wild-type and mutant "classical" nitroreductases of Salmonella typhimurium. L33R mutation greatly diminishes binding of FMN to the nitroreductase of S. typhimurium. J Biol Chem. 1998 Sep 11;273(37):23922-8.
15 Identification and functional characterization of arylamine N-acetyltransferases in eubacteria: evidence for highly selective acetylation of 5-aminosalicylic acid. J Bacteriol. 2001 Jun;183(11):3417-27.
16 Sepiapterin reductase mediates chemical redox cycling in lung epithelial cells. J Biol Chem. 2013 Jun 28;288(26):19221-37.
17 Time series analysis of oxidative stress response patterns in HepG2: a toxicogenomics approach. Toxicology. 2013 Apr 5;306:24-34.
18 Global gene expression analysis reveals differences in cellular responses to hydroxyl- and superoxide anion radical-induced oxidative stress in caco-2 cells. Toxicol Sci. 2010 Apr;114(2):193-203. doi: 10.1093/toxsci/kfp309. Epub 2009 Dec 31.