Dequalinium Chloride

Names

[ CAS No. ]:
522-51-0

[ Name ]:
Dequalinium Chloride

[Synonym ]:
Quinolinium, 1,1'-(1,10-decanediyl)bis[4-amino-2-methyl-, dichloride
DECA
efisol
dekamin
evazol
le chlorure de dequalinium
dekadin
EINECS 208-330-9
1,1'-Decan-1,10-diylbis(4-amino-2-methylchinolinium)dichlorid
BADQ-10
1,1'-(1,10-Decanediyl)bis(4-amino-2-methylquinolinium) dichloride
dequadin
eriosept
1,1'-Decane-1,10-diylbis(4-amino-2-methylquinolinium) dichloride
Dequalinium Chloride
dequavet
baqd10
Dequadin chloride
Quinolinium, 1,1'-(1,10-decanediyl)bis[4-amino-2-methyl-, chloride (1:2)
MFCD00063502
Dequalinium (Chloride)

Biological Activity

[Description]:

Dequalinium Chloride is a selective blocker of apamin-sensitive K+ channels.Target: Potassium ChannelDequalinium Chloride is a selective blocker of apamin-sensitive K+ channels. Treatment with Dequalinium chloride did not influence conditions caused by haemolytic streptococci -- verified by bacteriological examinations of pharyngeal smears -- inspite of its efficiency in vitro [1]. Dequalinium chloride (DECA), a cationic, lipophilic mitochondrial poison, selectively targets the mitochondrial membrane of certain epithelial carcinoma cells, in which it inhibits cellular energy production. Higher DECA doses under either regimen induced severe toxic effects and mortality [2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Potassium Channel

Research Areas >> Infection

[References]

[1]. Kramer, W., [Treatment of tonsillitis with dequalinium chloride]. Fortschr Med, 1977. 95(16): p. 1108-10.

[2]. Gamboa-Vujicic, G., et al., Toxicity of the mitochondrial poison dequalinium chloride in a murine model system. J Pharm Sci, 1993. 82(3): p. 231-5.

[Related Small Molecules]

Chemical & Physical Properties

[ Melting Point ]:
≥300 °C(lit.)

[ Molecular Formula ]:
C₃₀H₄₀Cl₂N₄

[ Molecular Weight ]:
527.571

[ Exact Mass ]:
526.263000

[ PSA ]:
59.80000

[ LogP ]:
1.34060

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VA0700000

CHEMICAL NAME :: Quinaldinium, 1,1'-decamethylenebis(4-amino-, dichloride

CAS REGISTRY NUMBER :: 522-51-0

LAST UPDATED :: 199603

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C30-H40-N4.2Cl

MOLECULAR WEIGHT :: 527.64

WISWESSER LINE NOTATION :: T66 BKJ C1 EZ B10- BT66 BKJ C1 EZ &Q 2 &G 2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 18300 ug/kg

TOXIC EFFECTS :: Liver - fatty liver degeneration Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 82,231,1993

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 70 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 8,110,1956

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1900 ug/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 8,110,1956 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 90 mg/kg/15W-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: JPMSAE Journal of Pharmaceutical Sciences. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.50- 1961- Volume(issue)/page/year: 82,231,1993

Safety Information

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
VA0700000

[ HS Code ]:
2933499090

Customs

[ HS Code ]: 2933499090

[ Summary ]:
2933499090. other compounds containing in the structure a quinoline or isoquinoline ring-system (whether or not hydrogenated), not further fused. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Antimicrobial topical agents used in the vagina.

Curr. Probl. Dermatol. 40 , 36-47, (2011)

Vaginally applied antimicrobial agents are widely used in the vagina in women with lower genital tract infections. An 'antimicrobial' is a general term that refers to a group of drugs that are effecti...

Dequalinium induces cytotoxicity in human leukemia NB4 cells by downregulation of Raf/MEK/ERK and PI3K/Akt signaling pathways and potentiation of specific inhibitors of these pathways.

Leuk. Res. 38(7) , 795-803, (2014)

Delocalized lipophilic cation dequalinium (DQA) selectively accumulates in mitochondria and displays anticancer activity in different malignancies. Our previous studies indicate a DQA-induced cytotoxi...

N-palmitoyl-ethanolamine (PEA) induces peripheral antinociceptive effect by ATP-sensitive K+-channel activation.

J. Pharmacol. Sci. 118(2) , 156-60, (2012)

Although the antinociceptive effects of N-palmitoyl-ethanolamine (PEA) were first characterized nearly 50 years ago, the identity of the mechanism that mediates these actions has not been elucidated. ...