General Information of Drug (ID: DR1022)
Drug Name
Menadione
Synonyms
Menadion; Menadionum; Menaphthon; Menaphthone; Menaphtone; Menaquinone 0; Mitenon; Mitenone; Panosine; Prokayvit; Synkay; Aquakay; Aquinone; Hemodal; Juva-K; K-Thrombyl; K-Vitan; Kaergona; Kanone; Kappaxin; Karcon; Kareon; Kativ-G; Kayklot; Kaykot; Kayquinone; Kipca-Oil Soluble; Klottone; Koaxin; Kolklot; Thyloquinone; Vitamin K 3; Vitamin K0; Vitamin K2(0); Vitamin K3; menadione; 2-Methyl-1,4-naphthalenedione; 2-Methyl-1,4-naphthochinon; 2-Methyl-1,4-naphthoquinone; 2-Methylnaphthoquinone; 2-methylnaphthalene-1,4-dione; 58-27-5; Kipca
Indication Vitamin deficiency [ICD11: 5B55] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 172.18 Topological Polar Surface Area 34.1
Heavy Atom Count 13 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
4055
PubChem SID
7751 ; 70547 ; 607330 ; 853737 ; 853809 ; 3133921 ; 6380040 ; 7849394 ; 7891061 ; 8136904 ; 8149919 ; 8152543 ; 10321386 ; 10528213 ; 11112142 ; 11120351 ; 11120839 ; 11121327 ; 11335255 ; 11341462 ; 11360494 ; 11361645 ; 11364122 ; 11364936 ; 11366684 ; 11367498 ; 11369246 ; 11370060 ; 11373099 ; 11374123 ; 11375660 ; 11377408 ; 11378230 ; 11408337 ; 11446754 ; 11461466 ; 11466487 ; 11467607 ; 11485003 ; 11486213 ; 11487047 ; 11489010 ; 11492537 ; 11495042 ; 11532917 ; 11533196 ; 12016111 ; 14772598 ; 22389508 ; 24871411
ChEBI ID
ChEBI:28869
CAS Number
58-27-5
TTD Drug ID
D03GET
Formula
C11H8O2
Canonical SMILES
CC1=CC(=O)C2=CC=CC=C2C1=O
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
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[3]
Methionine synthase reductase (MTRR) DME0431 Homo sapiens
MTRR_HUMAN
1.16.1.8
[4]
Methylenetetrahydrofolate reductase (MTHFR) DME0083 Homo sapiens
MTHR_HUMAN
1.5.1.20
[5]
NADPH-dependent carbonyl reductase 1 (CBR1) DME0067 Homo sapiens
CBR1_HUMAN
1.1.1.184
[6]
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Homo sapiens
CBR3_HUMAN
1.1.1.184
[7]
NADPH:quinone reductase (CRYZ) DME0468 Homo sapiens
QOR_HUMAN
1.6.5.5
[8]
Nitroreductase (NTR) DME1063 Salmonella enterica
A0A5K1UB29_SALTM
1.5.1.39
[9] , [10]
Sepiapterin reductase (SPR) DME0570 Homo sapiens
SPRE_HUMAN
1.1.1.153
[11]
Unclear metabolic mechanism (DME-unclear) DME1271 Faecalibacterium prausnitzii Not Available Not Available [12]
⏷ Show the Full List of 11  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
NADPH-dependent carbonyl reductase 3 (CBR3) DME0068 Km = 0.043 microM
CBR3_HUMAN
[7]
Methionine synthase reductase (MTRR) DME0431 Km = 0.0177 microM
MTRR_HUMAN
[4]
References
1 Menadione was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Rat hepatic CYP1A1 and CYP1A2 induction by menadione. Toxicol Lett. 2005 Feb 15;155(2):253-8.
3 CYP2E1 overexpression alters hepatocyte death from menadione and fatty acids by activation of ERK1/2 signaling. Hepatology. 2004 Feb;39(2):444-55.
4 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.
5 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.
6 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.
7 Different functions between human monomeric carbonyl reductase 3 and carbonyl reductase 1. Mol Cell Biochem. 2008 Aug;315(1-2):113-21.
8 Role of glutathione reductase during menadione-induced NADPH oxidation in isolated rat hepatocytes. Biochem Pharmacol. 1987 Nov 15;36(22):3879-84.
9 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.
10 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.
11 Sepiapterin reductase mediates chemical redox cycling in lung epithelial cells. J Biol Chem. 2013 Jun 28;288(26):19221-37.
12 Quinones are growth factors for the human gut microbiota. Microbiome. 2017 Dec 20;5(1):161.

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