General
Preferred name
DEQUALINIUM
Synonyms
DEQUALINIUM CHLORIDE ()
Dequalinium chloride hydrate ()
Dequafungan ()
Danical ()
Decabis ()
Dequalinium dichloride ()
Dequalinium (Chloride) ()
Cloruro de decualinio ()
Labosept ()
Dequadin ()
Dequacets ()
Decamine ()
Nordman ()
Fluomizin ()
GNF-Pf-5483 ()
Chlorure de dequalinium ()
NSC-166454 ()
Dekamin ()
BAQD 10 ()
BAQD-10 ()
Dequalinium cation ()
P&D ID
PD006879
CAS
6707-58-0
522-51-0
Tags
available
drug
Drug indication
Myelopathy
Drug Status
approved
investigational
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA Dequalinium has a multiple mode of action. It disrupts the cell permeability of the bacteria by absorbing onto the bacterial cell surface and diffusing across the membrane. It also binds to the cytoplasmic membrane with subsequent formation of complexes and protein precipitation and lyses the membrane in adequate concentrations, perturbing osmotic exchange. Loss of normal enzymatic activity is achieved through several different processes. Denaturation of proteins results in inhibition of bacterial cell metabolism. Disruption of bacterial energy production is mediated through inhibition of glucose metabolism and inhibition of mitochondrial ATP synthesis via inhibition of bacterial F1-ATPase. Protein synthesis is also terminated at the level of ribosomes. Bacterial nucleic acids are also affected through direct binding of the drug to DNA in vitro, and precipitation of cytoplasmic material with nucleic acids being the most sensitive [A19280]. ; The cationic form of dequalinium accumulates in the mitochondria and promotes anticancer activity in human leukemia cells. It mediates a cytotoxic effect by altering redox balance in cells and downregulating Raf/MEK/ERK1/2 and PI3K/Akt signaling pathways in these cells which leads to cell death by apoptosis and/or necrosis [A19290, A19291, A19292]. ; Dequalinium inhibits mycothiol ligase activity in Mycobacterium tuberculosis strains [A19298].
DESCRIPTION While the INN-assigned preparation of dequalinium is in complex with chloride, the compound is also available experimentally as the 'parent' salt form. Two of the references listed here refer to the parent compound, while and refer to dequalinium chloride. We show the structure of the parent compound, and our external links are also to this structure. (GtoPdb)
DESCRIPTION Selective blocker of apamin-sensitive K+ channels (LOPAC library)
DESCRIPTION Dequalinium Chloride is a PKC inhibitor with IC50 of 7-18 μM, and also a selective blocker of apamin-sensitive K+ channels with IC50 of 1.1 μM. (BOC Sciences Bioactive Compounds)
Cell lines
0
Organisms
5
Compound Sets
28
BOC Sciences Bioactive Compounds
dequalinium-chloride-cas-522-51-0-item-84-300567
Cayman Chemical Bioactives
17557
ChEMBL Approved Drugs
CHEMBL121663
CHEMBL333826
ChEMBL Drugs
CHEMBL121663
CHEMBL333826
Concise Guide to Pharmacology 2017/18
2313
Concise Guide to Pharmacology 2019/20
2313
Concise Guide to Pharmacology 2021/22
2313
Concise Guide to Pharmacology 2023/24
2313
CZ-OPENSCREEN Bioactive Library
Drug Repurposing Hub
DrugBank
DB04209
DrugBank Approved Drugs
DB04209
DrugCentral
4376
DrugCentral Approved Drugs
4376
DrugMAP
DMXM19W
DrugMatrix
EU-OPENSCREEN Bioactive Compound Library
EOS102343
Guide to Pharmacology
2313
Ki Database
Dequalinium
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL121663
CHEMBL333826
MedChem Express Bioactive Compound Library
HY-B0567
NIH Mechanistic Set
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
TargetMol Bioactive Compound Library
T0979
The Spectrum Collection
External IDs
56
Properties
(calculated by RDKit )
Molecular Weight
456.32
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
2
Rotatable Bonds
11
Ring Count
4
Aromatic Ring Count
4
cLogP
6.17
TPSA
59.8
Fraction CSP3
0.4
Chiral centers
0.0
Largest ring
6.0
QED
0.21
Structural alerts
2
aggregator (ZINC)
Aggregators
aggregator (Aggregator Advisor)
Aggregators
Related compounds
Custom attributes
(extracted from source data)
Pathway
Cytoskeletal Signaling
Anti-infection
Apoptosis
Membrane Transporter/Ion Channel
Neuronal Signaling
Target
PKC
KCNN1, KCNN3
Bacterial
nAChR
Parasite
Potassium Channel
Indication
first-aid antiseptic
MOA
PKC inhibitor
Source data