General Information of Drug (ID: DMMEQUR)

Drug Name
Ethidium
Synonyms
Ethidium; homidium; Ethidium cation; Novidium; 3546-21-2; UNII-EN464416SI; 3,8-Diamino-5-ethyl-6-phenylphenanthridinium; Phenanthridinium, 3,8-diamino-5-ethyl-6-phenyl-; BRN 3627183; CHEBI:42478; EN464416SI; AB00053825_07; CHEMBL284328; NSC84423; NSC522843; 5-ethyl-6-phenyl-phenanthridin-5-ium-3,8-diamine; 5-ethyl-6-phenylphenanthridin-5-ium-3,8-diamine; C21H20N3; Spectrum_001500; AC1L1GCK; Spectrum2_001587; Spectrum5_001263; Spectrum4_000198; UPCMLD-DP076; NCIMech_000529; cid_3624; Piperine & Ethidium bromide; NCIOpen2_009324
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 314.4
Logarithm of the Partition Coefficient (xlogp) 4.2
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 2
Chemical Identifiers
Formula
C21H20N3+
IUPAC Name
5-ethyl-6-phenylphenanthridin-5-ium-3,8-diamine
Canonical SMILES
CC[N+]1=C2C=C(C=CC2=C3C=CC(=CC3=C1C4=CC=CC=C4)N)N
InChI
InChI=1S/C21H19N3/c1-2-24-20-13-16(23)9-11-18(20)17-10-8-15(22)12-19(17)21(24)14-6-4-3-5-7-14/h3-13,23H,2,22H2,1H3/p+1
InChIKey
QTANTQQOYSUMLC-UHFFFAOYSA-O
Cross-matching ID
PubChem CID
3624
ChEBI ID
CHEBI:42478
CAS Number
3546-21-2
TTD ID
D0P0WG
VARIDT ID
DR01442

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human Deoxyribonucleic acid (hDNA) TTUTN1I NOUNIPROTAC Intercalator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
CD59 glycoprotein (CD59) OTSUMQDH CD59_HUMAN Gene/Protein Processing [3]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [4]
Cytochrome b (CYTB) OTAHB98A CYB_HUMAN Gene/Protein Processing [5]
Cytochrome c oxidase subunit 1 (COX1) OTG3O9BN COX1_HUMAN Gene/Protein Processing [6]
Cytochrome c oxidase subunit 2 (COX2) OTTMVBJJ COX2_HUMAN Gene/Protein Processing [5]
NADH-ubiquinone oxidoreductase chain 1 (ND1) OTCLGIXV NU1M_HUMAN Gene/Protein Processing [5]
NADH-ubiquinone oxidoreductase chain 4 (ND4) OT4RQVAA NU4M_HUMAN Gene/Protein Processing [5]
Nuclear respiratory factor 1 (NRF1) OTOXWNV8 NRF1_HUMAN Gene/Protein Processing [5]
P2X purinoceptor 7 (P2RX7) OTNJ9XPL P2RX7_HUMAN Regulation of Drug Effects [7]
Solute carrier family 22 member 1 (SLC22A1) OT7817I4 S22A1_HUMAN Regulation of Drug Effects [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4569).
2 31P NMR spectra of ethidium, quinacrine, and daunomycin complexes with poly(adenylic acid).poly(uridylic acid) RNA duplex and calf thymus DNA. Biochemistry. 1989 Apr 4;28(7):2804-12.
3 Comparison of the mutagenic potential of 17 physical and chemical agents analyzed by the flow cytometry mutation assay. Mutat Res. 2006 Dec 1;602(1-2):14-25. doi: 10.1016/j.mrfmmm.2006.07.009. Epub 2006 Oct 11.
4 Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.
5 The effect of ethidium bromide and chloramphenicol on mitochondrial biogenesis in primary human fibroblasts. Toxicol Appl Pharmacol. 2012 May 15;261(1):42-9. doi: 10.1016/j.taap.2012.03.009.
6 Assessment of mitochondrial toxicity by analysis of mitochondrial protein expression in mononuclear cells. Cytometry B Clin Cytom. 2009 May;76(3):181-90. doi: 10.1002/cyto.b.20458.
7 A Thr357 to Ser polymorphism in homozygous and compound heterozygous subjects causes absent or reduced P2X7 function and impairs ATP-induced mycobacterial killing by macrophages. J Biol Chem. 2006 Jan 27;281(4):2079-86. doi: 10.1074/jbc.M507816200. Epub 2005 Nov 1.
8 Organic cation transporters OCT1, 2, and 3 mediate high-affinity transport of the mutagenic vital dye ethidium in the kidney proximal tubule. Am J Physiol Renal Physiol. 2009 Jun;296(6):F1504-13. doi: 10.1152/ajprenal.90754.2008. Epub 2009 Apr 8.