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Dequalinium chloride

Pharmaceutical Secondary Standard; Certified Reference Material

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Synonym(s):
1,1′-Decamethylenebis(4-aminoquinaldinium) dichloride
Empirical Formula (Hill Notation):
C30H40Cl2N4
CAS Number:
522-51-0
Molecular Weight:
527.57
EC Number:
208-330-9
MDL number:
MFCD00063502
PubChem Substance ID:
329823288
NACRES:
NA.24

grade

certified reference material
pharmaceutical secondary standard

Quality Level

300

Agency

traceable to Ph. Eur. D0430000

API family

dequalinium

CofA

current certificate can be downloaded

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

mp

≥300 °C (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

storage temp.

2-8°C

SMILES string

[Cl-].[Cl-].Cc1cc(N)c2ccccc2[n+]1CCCCCCCCCC[n+]3c(C)cc(N)c4ccccc34

InChI

1S/C30H38N4.2ClH/c1-23-21-27(31)25-15-9-11-17-29(25)33(23)19-13-7-5-3-4-6-8-14-20-34-24(2)22-28(32)26-16-10-12-18-30(26)34;;/h9-12,15-18,21-22,31-32H,3-8,13-14,19-20H2,1-2H3;2*1H

InChI key

LTNZEXKYNRNOGT-UHFFFAOYSA-N

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General description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Dequalinium chloride (DECA) is a cationic, lipophilic mitochondrial toxin which can act as a cyctotoxic agent on the mitochondrial membrane of specific epithelial carcinoma cells, by inhibiting the cellular energy production. It can have useful applications in cancer therapy.

Application

Dequalinium chloride may be used as a pharmaceutical reference standard for the determination of the analyte in pharmaceutical formulations by high performance liquid chromatography (HPLC).
These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Analysis Note

These secondary standards offer multi-traceability to the USP, EP (PhEur) and BP primary standards, where they are available.

Other Notes

This Certified Reference Material (CRM) is produced and certified in accordance with ISO 17034 and ISO/IEC 17025. All information regarding the use of this CRM can be found on the certificate of analysis.

Footnote

To see an example of a Certificate of Analysis for this material enter LRAC3331 in the slot below. This is an example certificate only and may not be the lot that you receive.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Toxicity of the mitochondrial poison dequalinium chloride in a murine model system
Gamboa-Vujicic G, et al.
Journal of Pharmaceutical Sciences, 82(3), 231-235 (1993)
In-Hwan Lee et al.
Neurochemical research, 33(7), 1393-1400 (2008-03-07)
Intracellular toxic effects of the dequalinium-induced protofibrils of alpha-synuclein have been investigated with the yeast system expressing alpha-synuclein-GFP fusion protein in single copy, which appears in the green halo around the plasma membrane. Intracellular responses of the green fluorescent protein
Pilar Sancho et al.
Experimental biology and medicine (Maywood, N.J.), 237(8), 933-942 (2012-08-10)
Delocalized lipophilic cations, such as dequalinium (DQA), selectively accumulate in mitochondria and display anticancer activity in cells from different malignancies. Previous studies in K562 human leukemic cells indicate that DQA causes cell damage as a consequence of an early disturbance
Vladimir M Korkhov et al.
Journal of molecular biology, 377(4), 1094-1103 (2008-02-26)
EmrE is a Small Multidrug Resistance transporter (SMR) family member that mediates counter transport of protons and hydrophobic cationic drugs such as tetraphenylphosphonium (TPP+), ethidium, propidium and dequalinium. It is thought that the selectivity of the drug binding site in
[Statement of the Polish Gynecological Society expert panel concerning application of Fluomizin].
Ginekologia polska, 84(3), 237-239 (2013-05-25)
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